Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
From
US$534
/ night
Select dates to see prices and availability
From
US$534
/ night
About this property
Escape to our multiple-acre private paradise where you can enjoy breathtaking sunsets, gaze at countless stars, admire the wildlife, and dip into the water via our 200+ foot private beach. It's an ideal destination that you can enjoy for ho...
Location
Located in Chestertown, this vacation home is in the city center and on the beach. Rolphs Wharf Marina and Cassinelli Winery and Vineyards are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Garfield Center for the Arts at the Prince Theater and Larrabee Arts Center. Traveling with kids? Consider Crumpton Auction and The Mainstay. Kayaking and water tubing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and hunting nearby.
Pet friendly
Sauna
Refrigerator
Coffee/Tea maker
Cable/Satellite TV
Microwave
Guest reviews of Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
9.8
Exceptional
Based on 66 verified reviews
What guests think
AI-generated summary based on recent guest reviews
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! is praised for its peaceful Chester River setting, scenic views and sunsets, abundant wildlife, and a private, quiet atmosphere that offers a restorative escape within an easy drive of Chestertown.
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What guests think
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown! is praised for its peaceful Chester River setting, scenic views and sunsets, abundant wildlife, and a private, quiet atmosphere that offers a restorative escape within an easy drive of Chestertown.
Guests consistently describe the home as clean, spacious, comfortable, and well appointed, with attractive decor and flexible layouts for families and groups. Popular amenities include kayaks and paddleboards with a private pier, a screened porch, a fire pit, a large yard, and indoor games such as foosball. Hosts are friendly, communicative, and helpful, though one reviewer mentioned clutter in some areas and exterior maintenance needing attention. Expect a quiet, well-equipped riverside retreat suited to relaxed gatherings.
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AI-generated summary based on recent guest reviews
Facilities
Guests repeatedly praise the kayaks and paddleboards with a private pier, along with the screened porch, fire pit, and spacious yard. Indoor games (e.g., foosball) and touches like an illuminated pier are also appreciated.
Related guest reviews
10
Madeleine S.
30 Dec 2023
·
Stayed 2 nights
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
10
Elyce R.
19 Aug 2023
·
Stayed 7 nights
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
10
Amy K.
9 Jun 2025
·
Stayed 2 nights
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
10
Karin C.
22 Sept 2023
·
Stayed 3 nights
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
10
Linda E.
7 Oct 2024
·
Stayed 4 nights
This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.
This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.
10
Cindy D.
3 Jun 2024
·
Stayed 2 nights
We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!
We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!
10
Pat O.
30 Jun 2024
·
Stayed 8 nights
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
10
Emily L.
28 May 2023
·
Stayed 3 nights
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
10
Karin C.
23 Sept 2024
·
Stayed 3 nights
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
10
Lynda M.
15 Mar 2023
·
Stayed 4 nights
The illuminated pier at night was a treat!
The illuminated pier at night was a treat!
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AI-generated summary based on recent guest reviews
Cleanliness
Reviews consistently describe the home as clean and well maintained. One guest noted clutter in some areas and exterior upkeep needing attention.
Related guest reviews
10
Madeleine S.
30 Dec 2023
·
Stayed 2 nights
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
10
Carter F.
12 Jan 2025
·
Stayed 2 nights
Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
10
Elyce R.
19 Aug 2023
·
Stayed 7 nights
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
10
Amy K.
9 Jun 2025
·
Stayed 2 nights
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
10
Pat O.
30 Jun 2024
·
Stayed 8 nights
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
8
Debbie F.
22 Sept 2023
·
Stayed 3 nights
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
10
Betsy W.
25 Sept 2025
·
Stayed 2 nights
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
10
Emily L.
28 May 2023
·
Stayed 3 nights
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
10
Adam B.
17 Sept 2023
·
Stayed 2 nights
Our adult family stayed for the weekend to attend a nearby wedding. Property is expansive with all the amenities that you can imagine. House is clean, well equipped and beautifully situated. I highly recommend.
Our adult family stayed for the weekend to attend a nearby wedding. Property is expansive with all the amenities that you can imagine. House is clean, well equipped and beautifully situated. I highly recommend.
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AI-generated summary based on recent guest reviews
Rooms
Rooms are spacious, comfortable, and tastefully decorated, with multiple seating and sleeping areas that work well for families and groups.
Related guest reviews
10
Madeleine S.
30 Dec 2023
·
Stayed 2 nights
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
My family and I stayed over the Christmas holiday and had a wonderful time. The house was cozy, clean, and well appointed. We enjoyed the water views and it was great to be able to use the fireplaces. We would definitely return for another visit and highly recommend to anyone considering!
10
Carter F.
12 Jan 2025
·
Stayed 2 nights
Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again.
10
Amy K.
9 Jun 2025
·
Stayed 2 nights
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
10
Karin C.
22 Sept 2023
·
Stayed 3 nights
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
10
Cindy D.
3 Jun 2024
·
Stayed 2 nights
We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!
We really enjoyed our stay here. It was well appointed with kayaks and other outdoor activities, comfortable and beautiful views from the within the and the kitchen supplies were wonderful!! It is situated right on the river and we enjoyed our morning coffee at the end of the short pier. We are hoping to return!!!
10
Crystal P.
22 Jun 2023
·
Stayed 3 nights
This home was a lovely place to stay and relax. Very charming. Beautifully decorated but still comfortable. After 3 days in D.C., this was a great getaway. If we get back to the Maryland area, will likely stay here again if available. ❤️
This home was a lovely place to stay and relax. Very charming. Beautifully decorated but still comfortable. After 3 days in D.C., this was a great getaway. If we get back to the Maryland area, will likely stay here again if available. ❤️
10
Pat O.
30 Jun 2024
·
Stayed 8 nights
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
8
Debbie F.
22 Sept 2023
·
Stayed 3 nights
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
I have to start by saying that the property was not exactly as pictured. The pictures show a tidy uncluttered space inside and out, but that was not the case. The screened in porch was cluttered with too much furniture and other items. Some other spaces of the home were more cluttered than pictured as well. There were lights duct taped under the kitchen cabinets that were falling down. The exterior property maintenance could have been much better. For what we paid, we expected more. With all of this being said, it is a great house on the river that was clean on the interior when we arrived. There were six of us and we had plenty of room. We enjoyed our weekend despite the disappointment in some areas.
10
Suzan B.
30 Sept 2025
·
Stayed 3 nights
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
10
Karin C.
23 Sept 2024
·
Stayed 3 nights
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
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AI-generated summary based on recent guest reviews
Service
Hosts are friendly, responsive, and communicative, often offering helpful local suggestions and maintaining smooth communication.
Related guest reviews
10
Michael F.
30 Mar 2024
·
Stayed 7 nights
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
10
Elyce R.
19 Aug 2023
·
Stayed 7 nights
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
We had an amazing week at this incredible waterside property. The home is exactly as pictured, and the outdoor space offered plenty to keep us entertained. Despite some rainfall making swimming/floating in the river not possible a few days, we had lots of other options. My husband took our 4 year-old kayaking, which she loved. During our week stay, we explored Chestertown (a quick drive away), visited Rock Hall, and did chartered cruises out of Chesapeake City and St. Michael’s. You can tell the hosts take great care in their riverside home, and we are so glad they decided to share it. We’d love to come back!
10
Bryn M.
22 Apr 2024
·
Stayed 2 nights
Beautiful home and property! Host was very communicative and even gave suggestions for places to go in town. Would definitely book again.
Beautiful home and property! Host was very communicative and even gave suggestions for places to go in town. Would definitely book again.
10
Betsy W.
25 Sept 2025
·
Stayed 2 nights
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
10
Emily L.
28 May 2023
·
Stayed 3 nights
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
Everything you would want in a vacation home right on the Chester River. Great location, clean, lots of toys to play with, both on the water and in the home. The manager is a delight to work with….what more can you say FABULOUS!
10
Suzan B.
30 Sept 2025
·
Stayed 3 nights
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
10
Melanie B.
31 Jul 2023
·
Stayed 3 nights
My two young kids loved swimming in the river. One has sensory needs and enjoyed the muddy waters immensely. The house was nicely set up to give my family of four and my mother in law a little privacy in the evenings. Would recommend and come again. Communication with hosts easy and prompt.
My two young kids loved swimming in the river. One has sensory needs and enjoyed the muddy waters immensely. The house was nicely set up to give my family of four and my mother in law a little privacy in the evenings. Would recommend and come again. Communication with hosts easy and prompt.
10
Kathryn W.
30 May 2023
·
Stayed 3 nights
Thank you for sharing your wonderful home with us! Everything was perfect for our stay-we look forward to staying again soon!
Thank you for sharing your wonderful home with us! Everything was perfect for our stay-we look forward to staying again soon!
10
John P.
17 Jun 2025
·
Stayed 4 nights
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
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AI-generated summary based on recent guest reviews
Location
Scenic, quiet riverside setting with privacy, wildlife, and sunsets. It is a short drive to Chestertown for shops and restaurants.
Related guest reviews
10
Amy K.
9 Jun 2025
·
Stayed 2 nights
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
This home on the Chester River exceeded expectations. It was super clean, bright & roomy. It had great sleeping options for a 7-person group of women. The backyard up against the river was terrific. The water was so still for kayaking. There are multiple seating areas: fire pit, table on the pier, table off of the patio. The screened in patio was wonderful to use.
10
Linda E.
7 Oct 2024
·
Stayed 4 nights
This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.
This is a great house! My husband fished off the dock and caught some catfish. We played board games on the long table and relaxed. We walked around Chestertown during the day and found a small fair for our 2-year-old grandson to visit. Each night, we sat around the firepit which overlooked the water - so lovely. Very quiet area.
10
Michael F.
22 Apr 2023
·
Stayed 3 nights
We have been back to Ina's beautiful house several times and each time is a pleasure. We enjoy the quiet, the birds, the river's ebbs and flows, and the spectacular sunsets.
We have been back to Ina's beautiful house several times and each time is a pleasure. We enjoy the quiet, the birds, the river's ebbs and flows, and the spectacular sunsets.
10
Betsy W.
25 Sept 2025
·
Stayed 2 nights
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
Beautiful location on the river, helpful and communicative owners, clean and comfortable. A great place for our family to gather for a wedding in the area.
10
Betty M.
5 Mar 2023
·
Stayed 2 nights
Our stay was short, but absolutely fantastic! Great house, stunning view. We will definitely be back it must be even more gorgeous in the summer. ♥️
Our stay was short, but absolutely fantastic! Great house, stunning view. We will definitely be back it must be even more gorgeous in the summer. ♥️
10
Suzan B.
30 Sept 2025
·
Stayed 3 nights
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
10
Suzan B.
25 May 2024
·
Stayed 2 nights
This was the perfect place to gather our family of 5 adults and our 3 fur babies to celebrate Mother’s Day over the weekend. The house is beautifully decorated and we thoroughly enjoyed the large property that was very private and had not only access to the water but also stunning views. We look forward to coming back.
This was the perfect place to gather our family of 5 adults and our 3 fur babies to celebrate Mother’s Day over the weekend. The house is beautifully decorated and we thoroughly enjoyed the large property that was very private and had not only access to the water but also stunning views. We look forward to coming back.
10
John P.
17 Jun 2025
·
Stayed 4 nights
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
10
kathy g.
23 Apr 2023
·
Stayed 4 nights
Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown
Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown
10
Michael F.
27 Oct 2024
·
Stayed 3 nights
We have enjoyed our stays here in all seasons, but autumn is particularly beautiful with the leaves changing color and the migratory birds passing through. Such a great breather from city life.
We have enjoyed our stays here in all seasons, but autumn is particularly beautiful with the leaves changing color and the migratory birds passing through. Such a great breather from city life.
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AI-generated summary based on recent guest reviews
Dining
The kitchen is well stocked and well appointed for cooking, and several guests enjoyed restaurants and provisions in nearby Chestertown.
Related guest reviews
10
Michael F.
30 Mar 2024
·
Stayed 7 nights
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
We have come to this wonderful get away on the Chester river again and again over the last 4 years. We never grow inured to its charms. For us the glorious sunsets, peaceful evenings, and avian visitations create a state of continuous wonder. We have fallen in love with the quiet peace of the place. Ina has always been a caring and responsive host. And Chestertown is a great source of indulgent provisions.
10
Karin C.
22 Sept 2023
·
Stayed 3 nights
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
This is a lovely property with beautiful river views and no neighbors in sight. The house is well outfitted with everything we needed and extras like a fooseball table. It even had a "community pantry" with take-one-leave-one treats. The beds were comfortable and there were lots of places to sit and eat, play games, and do a jigsaw puzzle. Our two adult daughters said they would like to return, so that is high praise indeed.
10
Pat O.
30 Jun 2024
·
Stayed 8 nights
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
This is our second stay at this home and we loved it just as much as the first time. The location on the Chester River is wonderful. We used the kayaks and paddle boards every day. The home was immaculate and the kitchen well appointed. We enjoyed sitting and eating on the screened in porch and sipping wine around the fire pit every night. Our adult children stayed with us and there was ample room for relaxing and gathering around the large dinner table. Chestertown is just a short drive away and great for shopping and dining. We will definitely be back.
10
Suzan B.
30 Sept 2025
·
Stayed 3 nights
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
This was our third time hosting a family gathering at this site. The house is well equipped, beautifully furnished, and sits on a property that provides easy access to the river, a spectacular view and privacy. It’s also a short drive to nearby stores, restaurants and a farmers market. The host is also very friendly and available if you have any questions or concerns.
10
Karin C.
23 Sept 2024
·
Stayed 3 nights
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
It was our second time staying. The house is lovely with lots of homey touches--books, games, throw blankets. And the grounds are lovely -- a big yard right on the river. We loved kayaking and letting our dog explore the yard and the river front. The kitchen is well stocked (but if you have a favorite pan you might want to bring that). The screened in porch was a favorite place to eat and play games looking at the beautiful view. I hope we can return some time soon.
10
John P.
17 Jun 2025
·
Stayed 4 nights
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
We enjoyed our stay in Chestertown. It was very quiet and peaceful. The house had everything needed in regards to amenities. Our favorite part was the screened in porch where we enjoyed our morning coffee and breakfast. It’s a short ride into town where there is a supermarket in case anything is needed. The local restaurants were very good. If you need a more lively atmosphere then will have to drive out a bit to Chesapeake area but if looking to getaway from it all you can’t go wrong here. We bought our dog who loved the huge yard and the big shady tree to lay under. One warning is that if you bring pets that there are deer in the area. Just be careful of the surroundings. Thank you to Ina and Maynor for a wonderful stay.
10
kathy g.
23 Apr 2023
·
Stayed 4 nights
Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown
Beautiful property on the river . lots of amenities. Quick drive into quaint Chestertown
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AI-generated summary based on recent guest reviews
10
Michael F.
8 Apr 2026
·
Stayed 7 nights
We love coming here for peaceful getaways of bird watching and quiet days on the river.
We love coming here for peaceful getaways of bird watching and quiet days on the river.
10
David J.
8 Mar 2026
·
Stayed 2 nights
This property was great for families and pets. Very accessible waterfront for dogs. It had nice and relaxing fire pit area and outdoor sauna was a fun experience. The house had everything that we needed. Quick responses from host
This property was great for families and pets. Very accessible waterfront for dogs. It had nice and relaxing fire pit area and outdoor sauna was a fun experience. The house had everything that we needed. Quick responses from host
10
Cory F.
11 Jan 2026
·
Stayed 3 nights
Location. Host was commutative and helped with process.
Location. Host was commutative and helped with process.
10
Michael F.
2 Jan 2026
·
Stayed 4 nights
Even in the darkest days around the winter solstice the beauty of the river at the house is a wonder. We welcomed in a new year by sweating out the old year in the sauna and by communing with the cacophonous geese and the stoic eagles. Wishing all of us new beginnings in 2026!
Even in the darkest days around the winter solstice the beauty of the river at the house is a wonder. We welcomed in a new year by sweating out the old year in the sauna and by communing with the cacophonous geese and the stoic eagles. Wishing all of us new beginnings in 2026!
10
Nick O.
11 Dec 2025
·
Stayed 3 nights
Had a wonderful visit! Beautiful home
Had a wonderful visit! Beautiful home
Property policies
Check-in
Check-out
Check-in from 15:00
Before 11:00
FAQs about Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Are pets allowed at the property?
Pets are allowed, with a limit of two dogs. Service animals are exempt from this restriction. Guests are requested not to allow pets on the furniture.
What are the check-in and check-out times?
Check-in time is at 15:00 and check-out time is at 11:00. Early or late check-in/check-out options and any associated costs are not specified.
What accessibility features are available for guests with disabilities?
The property has limited wheelchair accessibility features, including step-free entrances and some wheelchair-accessible facilities.
Where is the property located in relation to key landmarks?
The property is located in Chestertown, Maryland, in the city center and on the beach. It is close to Rolphs Wharf Marina, Cassinelli Winery and Vineyards, and various local attractions such as the Garfield Center for the Arts and Larrabee Arts Center.
Are children allowed at the property?
Children are allowed at the property, with ages 0-17 permitted to stay for free.
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Instant AI responses are based on hotel information
Check-in must be done by someone who is at least 21 years old.
Popular amenities
Pet friendly
Sauna
Refrigerator
Coffee/Tea maker
Cable/Satellite TV
Microwave
General
Pet friendly
Sauna
Refrigerator
Cable/Satellite TV
Coffee/Tea maker
Microwave
Hair dryer
Desk
Shower
Ice machine
Fireplace
Beach Sun Loungers
Children's Games
Smoke-Free Property
Wheelchair Accessible (Limited)
Activities
Garden
Playground
Kayaking
Hiking
Fitness facilities
Bicycle (on site)
Books
Firepit
Games
Hiking/Biking (nearby)
Outdoor Furniture
Public Winery Tours
Services
Laundry Facilities
Internet
Free wi-fi