The Oaks Waterfront Hotel
From
US$480
/ night
Select dates to see prices and availability
From
US$480
/ night
About this property
Don't miss out on recreational opportunities including a seasonal outdoor pool and bicycles to rent. This bed & breakfast also features complimentary wireless internet access, concierge services, and a picnic area.
Amenities
Don't miss out on recreational opportunities including a seasonal outdoor pool and bicycles to rent. This bed & breakfast also features complimentary wireless internet access, concierge services, and a picnic area.
Business amenities
Featured amenities include a business center, a 24-hour front desk, and luggage storage. Free self parking is available onsite.
Dining
At The Oaks Waterfront, enjoy a satisfying meal at the restaurant. Wrap up your day with a drink at the bar/lounge. A complimentary cooked-to-order breakfast is served daily.
Rooms
Stay in one of 15 guestrooms featuring Smart televisions. Complimentary wireless internet access keeps you connected, and digital programming is available for your entertainment. Private bathrooms have complimentary toiletries and hair dryers. Conveniences include complimentary bottled water and irons/ironing boards, and housekeeping is provided daily.
Location
Located in Easton, The Oaks Waterfront is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery. This bed & breakfast is 16.9 mi (27.2 km) from Chesapeake Bay and 3.6 mi (5.7 km) from Windon Distilling.
What's nearby
Saint Michaels Village(2.9 Miles)
St. Michaels Winery(3.5 Miles)
Windon Distilling(3.6 Miles)
Classic Motor Museum(3.6 Miles)
St. Michaels Museum(3.7 Miles)
Saint Marys Square(3.7 Miles)
Back Creek Park(3.8 Miles)
Saint Marys Square Museum(3.8 Miles)
Church Cove Park(3.8 Miles)
Muskrat Park(3.9 Miles)
St. Michaels Marina(3.9 Miles)
Higgins Yacht Yard and Marina(4 Miles)
Clint S. Bradley Park(4 Miles)
Saint Michaels Town Hall(4.1 Miles)
Chesapeake Bay Maritime Museum(4.2 Miles)
Easton, MD (ESN-Easton - Newnam)(9.9 Miles)
Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional)(60.5 Miles)
Parking
Restaurant
Swimming pool
Non-smoking rooms
Tour desk
Housekeeping
Location
25876 Royal Oaks Road, Easton, Maryland, United States of America
Saint Michaels Village (2.9 Miles)
St. Michaels Winery (3.5 Miles)
Windon Distilling (3.6 Miles)
Classic Motor Museum (3.6 Miles)
St. Michaels Museum (3.7 Miles)
Saint Marys Square (3.7 Miles)
Room options
3
Deluxe Room, 1 Queen Bed
Room details
1 Large Double Bed
Sleeps 2
Air ConditioningHeated FloorWi-Fi (Free)
1
Junior Suite, 1 King Bed with Sofa Bed
Room details
1 Extra-Large Double Bed
and 1 Sofa Bed
Sleeps 4
Air ConditioningHeated FloorWi-Fi (Free)
2
Deluxe Room, 1 King Bed
Room details
1 Extra-Large Double Bed
Sleeps 2
Air ConditioningHeated FloorWi-Fi (Free)
1
Luxury Cottage, 1 King Bed, River View
Room details
1 Extra-Large Double Bed
Sleeps 2
Separate Dining AreaAir ConditioningHeated FloorWi-Fi (Free)
5
Luxury Suite, 1 Bedroom, Balcony
Room details
1 Extra-Large Double Bed
and 1 Sofa Bed
Sleeps 4
BalconyAir ConditioningHeated FloorWi-Fi (Free)
1
Junior Suite, 1 King Bed, Balcony
Room details
1 Extra-Large Double Bed
Sleeps 2
BalconyBalcony or TerraceAir ConditioningHeated FloorWi-Fi (Free)
1
Deluxe Room, 2 Queen Beds
Room details
2 Large Double Beds
Sleeps 4
Air ConditioningHeated FloorWi-Fi (Free)
3
Luxury Cottage, 1 Bedroom, Kitchen, River View
Room details
1 Extra-Large Double Bed
Sleeps 2
Air ConditioningHeated FloorWi-Fi (Free)Fireplace
1
Deluxe Room, 1 King Bed, Private Bathroom
Room details
1 Extra-Large Double Bed
Sleeps 2
Air ConditioningHeated FloorWi-Fi (Free)
1
Deluxe Room, 1 King Bed, Accessible
Room details
1 Extra-Large Double Bed
Sleeps 2
Air ConditioningHeated FloorWi-Fi (Free)
Guest reviews of The Oaks Waterfront Hotel
9.8
Exceptional
Based on 283 verified reviews
Who stays here?
Business
5%
Couple
45%
Family
40%
Group
10%
What guests think
AI-generated summary based on recent guest reviews
At The Oaks Waterfront Hotel, reviewers highlight a beautifully renovated, tranquil waterfront property with immaculate grounds and welcoming, attentive staff, creating a relaxing escape that feels close to town yet pleasantly removed.
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What guests think
At The Oaks Waterfront Hotel, reviewers highlight a beautifully renovated, tranquil waterfront property with immaculate grounds and welcoming, attentive staff, creating a relaxing escape that feels close to town yet pleasantly removed.
Guests praise the well-kept waterfront grounds, outdoor decks and seating, a saltwater pool, and kayaks, canoes, paddle boards, and bikes, plus a shuttle into nearby St. Michaels. Rooms are freshly renovated, stylish, and comfortable, with several noting excellent beds. Breakfast is widely praised, while on-site dining and bar options beyond breakfast appear limited or inconsistent, so some guests head into town for other meals. Expect a peaceful, amenity-rich waterfront getaway.
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AI-generated summary based on recent guest reviews
Facilities
Guests frequently praise the well-kept grounds, outdoor decks and seating by the water, a saltwater pool, and kayaks, canoes, paddle boards, and bikes. A shuttle to St. Michaels adds convenience.
Related guest reviews
10
David
2 Sept 2025
·
Stayed 2 nights
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
10
Anna
4 Jul 2023
·
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
10
Howard
26 Aug 2025
·
Stayed 2 nights
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
10
John
10 Jul 2023
·
Stayed 2 nights
The property is very well maintained, staff is super friendly and property is newly renovated
The property is very well maintained, staff is super friendly and property is newly renovated
10
Debra
8 Sept 2023
·
Stayed 3 nights
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
10
James
8 Sept 2024
·
Stayed 3 nights
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
8
Thomas
16 Aug 2025
·
Stayed 1 night
The facility designed was out standing and the staff was very good.
The facility designed was out standing and the staff was very good.
10
EDMUND
4 May 2024
·
Stayed 2 nights
Beautiful facility and grounds and friendly staff.
Beautiful facility and grounds and friendly staff.
10
Bryan
31 May 2024
·
Stayed 2 nights
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
10
Erin
19 May 2024
·
Stayed 2 nights
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
Was this helpful?
AI-generated summary based on recent guest reviews
Cleanliness
Reviews consistently describe the property, common areas, and rooms as immaculate and impeccably maintained.
Related guest reviews
10
Lili
13 Aug 2023
·
Stayed 2 nights
Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.
Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.
10
Anna
4 Jul 2023
·
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
10
Howard
26 Aug 2025
·
Stayed 2 nights
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
10
John
10 Jul 2023
·
Stayed 2 nights
The property is very well maintained, staff is super friendly and property is newly renovated
The property is very well maintained, staff is super friendly and property is newly renovated
10
Debra
8 Sept 2023
·
Stayed 3 nights
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
10
Sarah
19 May 2024
·
Stayed 2 nights
Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!
Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!
10
Cary
4 Sept 2024
·
Stayed 1 night
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
10
Bryan
31 May 2024
·
Stayed 2 nights
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
10
Robert
19 Mar 2025
·
Stayed 3 nights
Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!
Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!
10
Deborah
22 Oct 2025
·
Stayed 1 night
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
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AI-generated summary based on recent guest reviews
Rooms
Rooms are newly renovated, tastefully decorated, and comfortable, with many noting excellent beds and quietly elegant accommodations.
Related guest reviews
10
Debra
8 Sept 2023
·
Stayed 3 nights
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
10
Richard
19 Feb 2024
·
Stayed 2 nights
Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there
Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there
10
Cary
4 Sept 2024
·
Stayed 1 night
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
10
Barbara
25 Jul 2025
·
Stayed 2 nights
Loved the Oaks! Fabulous accommodations and excellent staff
Loved the Oaks! Fabulous accommodations and excellent staff
10
Bryan
31 May 2024
·
Stayed 2 nights
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
10
FRANCES
9 Mar 2024
·
Stayed 3 nights
Wonderful place. Beautiful. Staff was top notch. Accommodations were outstanding.
Wonderful place. Beautiful. Staff was top notch. Accommodations were outstanding.
10
Erin
19 May 2024
·
Stayed 2 nights
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10
Deborah
22 Oct 2025
·
Stayed 1 night
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
10
Kate
3 Mar 2024
·
Stayed 2 nights
Exquisite and gracious service. Stunning appointments throughout. Just beautiful.
Exquisite and gracious service. Stunning appointments throughout. Just beautiful.
10
Jeffrey
1 Nov 2025
·
Stayed 3 nights
Staff, breakfast, and room were all superb!
Staff, breakfast, and room were all superb!
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AI-generated summary based on recent guest reviews
Service
Service stands out as friendly, attentive, and proactive, with quick responses and thoughtful extras like early breakfast bags and local recommendations.
Related guest reviews
10
David
2 Sept 2025
·
Stayed 2 nights
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
10
Anna
4 Jul 2023
·
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
10
James
28 Nov 2025
·
Stayed 2 nights
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.
10
Howard
26 Aug 2025
·
Stayed 2 nights
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
10
Debra
8 Sept 2023
·
Stayed 3 nights
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
10
Sarah
19 May 2024
·
Stayed 2 nights
Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!
Where to begin with this amazing stay? My husband and I went for a weekend to run the St. Michaels half marathon. We were looking for a quiet, relaxing place and the Oaks Waterfront surpassed our expectations. The property is impeccably maintained and, Linda, made us special early breakfast bags for the race since we would have to leave at 5AM, before breakfast service. She helped us find restaurants, get dinners, it was incredible. The property is so beautiful. We didn't bring our children but it would be a great place for them too!
10
Sarah
31 Jul 2023
·
Stayed 2 nights
I would give this property and staff a 12 if ratings went that high.
I would give this property and staff a 12 if ratings went that high.
10
Geeti
14 Apr 2024
·
Stayed 2 nights
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
10
Bryan
31 May 2024
·
Stayed 2 nights
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
10
Deborah
22 Oct 2025
·
Stayed 1 night
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
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AI-generated summary based on recent guest reviews
Location
The serene waterfront setting offers pleasant views, and the hotel is a short drive from downtown St. Michaels, with a shuttle available for trips into town.
Related guest reviews
10
Lili
13 Aug 2023
·
Stayed 2 nights
Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.
Our stay at the Oaks at Waterfront was wonderful. The hotel has gone through a major renovation and is absolutely beautiful. The staff were so helpful and friendly. No hesitation that we are coming back for another visit. Stay in this little gem of a inn in the St Michael’s area.
10
Anna
4 Jul 2023
·
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
We loved our stay here! The facility and grounds are immaculate. The staff, especially Linda, Lamond and Joe, make sure that you feel welcome and are taken care of. Serenity at its best! Highlights were (all included with stay) delicious gourmet breakfast, saltwater pool, on-site activities, and shuttle to town. Highly recommend The Oaks for your stay in St. Michaels! We will definitely be back!
10
Richard
19 Feb 2024
·
Stayed 2 nights
Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there
Outstanding boutique hotel on the water. Everything is new. Staff is fantastic. Lovely romantic weekend there
10
James
8 Sept 2024
·
Stayed 3 nights
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
8
Marka
3 Jun 2023
·
Stayed 3 nights
The property was recently renovated and is absolutely beautiful and relaxing. I think more eating and drinking options on the property would be helpful. The bar wasn’t really open and the only food option is breakfast at 8:30 am. You must leave the property and drive to town for all your drinks and meals which felt like a hassle sometimes.
The property was recently renovated and is absolutely beautiful and relaxing. I think more eating and drinking options on the property would be helpful. The bar wasn’t really open and the only food option is breakfast at 8:30 am. You must leave the property and drive to town for all your drinks and meals which felt like a hassle sometimes.
10
diane mc
23 Sept 2024
·
Stayed 2 nights
delightful and charming! great views and peaceful! We really enjoyed our stay!
delightful and charming! great views and peaceful! We really enjoyed our stay!
10
Cary
4 Sept 2024
·
Stayed 1 night
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
Gorgeous clean property, stunning location & comfy bed! Worth every penny and we will stay again!
10
Geeti
14 Apr 2024
·
Stayed 2 nights
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
10
Bryan
31 May 2024
·
Stayed 2 nights
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
The Oaks Waterfront Hotel is a beautiful property located only 3 miles from downtown St. Michael’s but felt like our own private getaway. The accommodations are quietly elegant and the grounds are wonderfully maintained. What really made our stay outstanding was the hotel staff, from our hostess, to our bartenders and servers and the gardener we met on our last day. Their hospitality and regard for their profession was apparent in how well we were considered in every service they provided. The property was beautiful and the staff was equally outstanding.
10
Erin
19 May 2024
·
Stayed 2 nights
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
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AI-generated summary based on recent guest reviews
Dining
Breakfast is widely praised for quality, but on-site dining and bar options beyond breakfast appear limited or inconsistent, so some guests head into town for other meals.
Related guest reviews
10
David
2 Sept 2025
·
Stayed 2 nights
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
10
Seth
21 Feb 2025
·
Stayed 2 nights
Beautiful property, wonderful staff, excellent food service.
Beautiful property, wonderful staff, excellent food service.
10
Debra
8 Sept 2023
·
Stayed 3 nights
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
Wonderful property. Staff was polite, helpful and friendly. Great options for breakfast and food was delicious. Kayaks were nice and easy launching area. King room with water view and balcony was comfortable and clean. Will return!!
10
James
8 Sept 2024
·
Stayed 3 nights
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
Gorgeous property, incredible landscaping, beautiful rooms, lots of decks, chairs by water, absolute delicious breakfast & dinners on the terrace. Kayak, canoe, bikes & paddle boards. Great salt water pool. The staff was extremely accommodating. Just a great tranquil place to go to just relax, eat, drink & enjoy each other. St. Michaels is just 5 minutes away to shop or just go eat. We had wonderful experience.
8
Marka
3 Jun 2023
·
Stayed 3 nights
The property was recently renovated and is absolutely beautiful and relaxing. I think more eating and drinking options on the property would be helpful. The bar wasn’t really open and the only food option is breakfast at 8:30 am. You must leave the property and drive to town for all your drinks and meals which felt like a hassle sometimes.
The property was recently renovated and is absolutely beautiful and relaxing. I think more eating and drinking options on the property would be helpful. The bar wasn’t really open and the only food option is breakfast at 8:30 am. You must leave the property and drive to town for all your drinks and meals which felt like a hassle sometimes.
10
Geeti
14 Apr 2024
·
Stayed 2 nights
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
Beautiful newly renovated picturesque place, we had a great weekend stay. It’s conveniently located close to Saint Michael and Easton downtown close to great food options, museums and shopping. Staff is attentive unobtrusive and Linda deserves a special mention for excellent recommendations for food and things to do. You can see Oaks is a great wedding venue with pretty interiors and exteriors and we were lucky to have a quiet weekend before it’s unavailable with weddings booked for the entire year. Want to especially mention the delicious breakfast and service every morning. We had a lovely stay and found lots of things to do close by. Highly recommend especially if looking for a top notch bed and breakfast experience with pretty deluxe touches all around.
10
Robert
19 Mar 2025
·
Stayed 3 nights
Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!
Beautiful decor, exceptional staff, food was delicious. Serene surroundings. Excellent stay!
10
Erin
19 May 2024
·
Stayed 2 nights
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10/10 beautifully renovated 1700s resort. Transportion available until 10 pm, chef made breakfast included in your stay. Great beds, canoes available to use.
10
Deborah
22 Oct 2025
·
Stayed 1 night
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
10
Jeffrey
1 Nov 2025
·
Stayed 3 nights
Staff, breakfast, and room were all superb!
Staff, breakfast, and room were all superb!
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AI-generated summary based on recent guest reviews
10
James
28 Nov 2025
·
Stayed 2 nights
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.
Our stay at The Oaks exceeded our expectations. It was recommended to us by a family friend. All staff were very informative and helpful. We will definitely make it a point to return.
10
Jeffrey
1 Nov 2025
·
Stayed 3 nights
Staff, breakfast, and room were all superb!
Staff, breakfast, and room were all superb!
10
Deborah
22 Oct 2025
·
Stayed 1 night
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
This was one of the nicest hotels I've stayed at. The property was absolutely beautiful. The public and guest rooms were immaculate and nicely decorated. All staff went out of their way to be helpful and make you feel welcome. We had breakfast and dinner in the restaurant and the food was phenomenal, and the beautiful view of the water was a bonus.
10
David
2 Sept 2025
·
Stayed 2 nights
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
Everyone and everything was great customer service is at all time best. The Oaks goes out of way to insure nice stay. Food although limited is still fantastic. The grounds are also spectacular. Hats of to Beth?
10
Howard
26 Aug 2025
·
Stayed 2 nights
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
Everything was amazing at The Oaks. So many places to find quiet and comfort — 2 nd floor deck, pier enclosure, outdoor Adirondack chairs. The welcoming area is quietly and responsibly staffed with beverages available 24/7. Assistance was always available texts answered immediately — nice touch. The luxurious bed and the heated bathroom floor added substantially to our lovely accommodations. The grounds and building interior and exterior were impeccably maintained. Loved our stay and only have scratched the surface on all the extras —pool, bicycles and kayaks. Will return, for sure.
FAQs about The Oaks Waterfront Hotel
Is parking available at the property?
Yes, free self-parking is available on-site. However, parking is limited.
What type of breakfast is offered and what are the serving hours?
A complimentary cooked-to-order breakfast is served daily. Specific serving hours are not provided.
Does the property allow pets?
Yes, pets are allowed in specific rooms only, with a fee of USD 150 per pet, per stay. Service animals are exempt from fees.
What are the standard check-in and check-out times?
Check-in is from 3:00 PM to 5:00 PM, and check-out is at 11:00 AM. Early or late check-in/check-out may be available upon request, and guests should contact the property at least 24 hours before arrival for arrangements.
What accessibility features are available for guests with disabilities?
The property features step-free entrances and wheelchair-accessible facilities in public areas. Specific details about room accessibility are not provided.
What is the location of the property in relation to key landmarks?
The property is located on the waterfront in Easton, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery. It is approximately 16.9 miles from Chesapeake Bay and 3.6 miles from Windon Distilling.
Is there a swimming pool at the property?
Yes, there is a seasonal outdoor pool, which is open from May to September.
What are the policies for guests staying with children?
Children are allowed at the property, but specific age policies regarding free stays for children are not provided.
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Instant AI responses are based on hotel information
Prices for upcoming dates
September 2026
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Cheaper
Pricier
Average nightly price across deals, with taxes & fees.
Prices in USD for 2 guests, updated daily.
- 2026-09-26: NO DATA
- 2026-09-27: 482.47604605407713USD
- 2026-09-28: 482.47604605407713USD
- 2026-09-29: NO DATA
- 2026-09-30: 482.47604605407713USD
- 2026-10-01: 482.47604605407713USD
- 2026-10-02: NO DATA
- 2026-10-03: NO DATA
- 2026-10-04: 482.20823518981933USD
- 2026-10-05: 483.6930489807129USD
- 2026-10-06: 483.16086874694827USD
- 2026-10-07: 483.14960567321776USD
- 2026-10-08: 482.47604605407713USD
- 2026-10-09: NO DATA
- 2026-10-10: NO DATA
- 2026-10-11: 482.47604605407713USD
- 2026-10-12: 482.47604605407713USD
- 2026-10-13: 483.6930489807129USD
- 2026-10-14: 483.58458975219725USD
- 2026-10-15: NO DATA
- 2026-10-16: NO DATA
- 2026-10-17: NO DATA
- 2026-10-18: 483.6930489807129USD
- 2026-10-19: NO DATA
- 2026-10-20: NO DATA
- 2026-10-21: 483.6930489807129USD
- 2026-10-22: NO DATA
- 2026-10-23: NO DATA
- 2026-10-24: NO DATA
- 2026-10-25: 482.47604605407713USD
- 2026-10-26: 482.47604605407713USD
- 2026-10-27: 483.6930489807129USD
- 2026-10-28: 482.47604605407713USD
- 2026-10-29: 483.7582983306885USD
- 2026-10-30: 493.50043995666505USD
- 2026-10-31: 483.6930489807129USD
- 2026-11-01: 483.7912184875488USD
- 2026-11-02: 483.49194749450686USD
- 2026-11-03: 483.6930489807129USD
- 2026-11-04: 483.6930489807129USD
- 2026-11-05: NO DATA
- 2026-11-06: NO DATA
- 2026-11-07: NO DATA
- 2026-11-08: 483.6930489807129USD
- 2026-11-09: 484.53597185668946USD
- 2026-11-10: 483.6930489807129USD
- 2026-11-11: NO DATA
- 2026-11-12: 483.7912184875488USD
- 2026-11-13: 482.47604605407713USD
- 2026-11-14: 482.47604605407713USD
- 2026-11-15: 483.60509967041014USD
- 2026-11-16: 537.4067866516114USD
- 2026-11-17: 482.47604605407713USD
- 2026-11-18: 482.47604605407713USD
- 2026-11-19: 483.58458975219725USD
- 2026-11-20: 483.7912184875488USD
- 2026-11-21: 482.47604605407713USD
- 2026-11-22: 483.7912184875488USD
- 2026-11-23: 537.5458021820068USD
- 2026-11-24: 483.6930489807129USD
- 2026-11-25: 483.58458975219725USD
- 2026-11-26: 483.7582983306885USD
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation. If you are planning to arrive after 5 PM please contact the property in advance using the information on the booking confirmation. Guests must contact the property in advance for check-in instructions. Front desk staff will greet guests on arrival at the property. For any questions, please contact the property using the information on the booking confirmation. Information provided by the property may be translated using automated translation tools. Check-in is from 3-5 PM.
Check-in must be done by someone who is at least 18 years old.
- Extra-person charges may apply and vary depending on property policy
- Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
- Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
- This property accepts credit cards; cash is not accepted
- Safety features at this property include a fire extinguisher, a smoke detector, and a first aid kit
- This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
- Please note that cultural norms and guest policies may differ by country and by property; the policies listed are provided by the property
- The seasonal pool will be open from May to September.
- Reservations are required for massage services. Reservations can be made by contacting the bed & breakfast prior to arrival, using the contact information on the booking confirmation.
Popular amenities
Parking
Restaurant
Swimming pool
Non-smoking rooms
Tour desk
Housekeeping
Services
Tour desk
Housekeeping
Banquet facilities
Safe-deposit box
Bicycle rental
Luggage storage
Designated smoking area
Express check-in/check-out
24-Hour Front Desk
Concierge Services
Parking
Parking
Free parking
Electric car charging station
Area Shuttle (free)
Parking (Limited)
Parking Onsite
Activities
Swimming pool
Garden
Golf course (nearby)
Cycling
Canoeing
Pool outdoor
Outdoor Fireplace
Outdoor Furniture
Pool (Seasonal Outdoor)
Terrace
General
Restaurant
Non-smoking rooms
Picnic area/Tables
Packed lunches
Beach Sun Loungers
Internet
Free wi-fi