Is parking available at the property?

Yes, free self-parking is available on-site, and it includes uncovered spaces. No reservation is required.

What are the check-in and check-out times?

Check-in is from 3:00 PM to 11:59 PM, and check-out is by 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 offers limited wheelchair accessibility, including a wheelchair-accessible registration desk and on-site restaurant. There are also designated parking spaces for wheelchair users.

Where is the property located in relation to key landmarks?

The Lodge at Great Oak Landing is located in Chestertown, approximately 8.8 miles from Washington College and 9.6 miles from Garfield Center for the Arts at the Prince Theater. It is also close to Chesapeake Bay, just 1.2 miles away.

Does the property have a swimming pool?

Yes, there is a seasonal outdoor swimming pool available from May 23 to September 18, operational from 10:00 AM to 8:00 PM.

Are children allowed at the property?

Children are allowed at the property, but specific age policies for free stays are not detailed.

The Lodge at Great Oak Landing

What guests think

At The Lodge at Great Oak Landing, guests highlight the scenic marina setting with a pool, private beach, and on-site dining, but note dated, small rooms plus inconsistent amenities such as unreliable Wi-Fi and occasional closures.

Staff are frequently praised as friendly and helpful, though some guests struggled to reach anyone at times. Cleanliness feedback is mixed, with some clean, comfortable stays and others reporting odors or maintenance grime. Best for relaxed getaways if you prioritize the grounds and vibe over modern rooms and guaranteed amenities.

Facilities

Cleanliness

Rooms

Service

Location

Dining

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AI-generated summary based on recent guest reviews

Facilities

Marina-style amenities such as the pool, private beach with chairs, on-site bar/entertainment, and even free golf are highlights for several guests. Recurring drawbacks include unreliable Wi-Fi, broken or unavailable machines, occasional seasonal closures (pool/Tiki bar), very cold pool water, and no elevator.

Related guest reviews

10

Stephen

19 Jul 2024

·

Stayed 3 nights

Great little gem in the middle of nowhere….beautiful pool….private beach…great restaurant….free golf course on the property too!!…what else can you ask for?…This is our new get away place away from everything….Chestertown is only a 10 minute drive,if you need supplies….10 stars😀

4

Pam

3 Nov 2024

·

Stayed 2 nights

We felt like we overpaid for what we got. Restaurant was not open. We were given 1 large towel and the rest were small. We did not have any maid service. The ice machine did not work. The coffee machine did not work. Beautiful marina. We felt like the only ones there.

8

Michael

26 Aug 2024

·

Stayed 2 nights

I was a first time visitor and was a bit disappointed when I received a phone call the morning of my arrival about the pool area being closed. The pool and the Tiki bar was all I had heard from others that I traveled with. I feel like I didn't get the full Great Oak Landing experience. with saying that the food at the restaurant was excellent and the staff were friendly and helpful, shoutout to Eden (barmaid) and Johnny who worked on the grounds and was very helpful with information.

4

Steve

27 Sept 2025

·

Stayed 1 night

WIFI did not work. As such WIFI TV apps (Netflix, Prime, etc) were unavailable.

6

George

16 Sept 2024

·

Stayed 1 night

Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.

10

Stephen

15 Jul 2025

·

Stayed 3 nights

We love this place….awesome pool,and free golf….couldn’t ask for more 😃

10

KEVIN

23 Sept 2024

·

Stayed 2 nights

Beautiful views, easy check in and safe, quiet area and the restaurant's food was on point and we loved the live band on Saturday night!! #shawnwasagreatcook #angelawasaexcellentwaitress

10

Ashley

16 Aug 2025

·

Stayed 1 night

Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site.

10

Stephen

20 Jul 2024

·

Stayed 3 nights

Great little gem in the middle of nowhere….beautiful pool….private beach…great restaurant….free golf course on the property too!!…what else can you ask for….10 stars😀

2

Thomas

29 Sept 2024

·

Stayed 1 night

This property is not being maintained at all. Staff work limited hours. Ice machine broken, coke machine removed, only coffee option is a communal K cup machine in the hallway. Water not available to refill it.

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AI-generated summary based on recent guest reviews

Cleanliness

Reports are mixed: some guests found rooms clean and fresh, while others noted odors, damp or dirty linens, stained or worn rugs, and grime on woodwork. A few also reported no housekeeping during their stay.

Related guest reviews

2

N. Kevin

6 Oct 2024

·

Stayed 3 nights

This hotel was not as advertised. We walked into room and it was like a broke down motel. There was someone’s hair all over the bed. No closet. Bathroom I think was the closet. We informed the front desk and We left immediately How do I get a refund.

6

Jennifer

22 Aug 2025

·

Stayed 1 night

Outdated. Room had a peculiar odor.

4

Ed

3 Oct 2024

·

Stayed 2 nights

At first I couldn't identify the smell but after an hour, I realized it was the scent of abandonment and isolation. The room was clean but everything was very basic. There was a TV but apparently no free programming. This, combined with spotty internet service and just a sense of creepiness led me to flee before dark.

2

Todd

18 Aug 2025

·

Stayed 1 night

Only pro was the bed was comfortable. The room was dirty and everything was old and very outdated. Floorboards, doors and fixtures were dirty. Shower floor was gross. Walls had rust, dirt and holes. Deck was unkempt and dirty. Did not eat there because I didn’t trust the cleanliness of their kitchen based on the room.

8

Paul

27 Oct 2024

·

Stayed 1 night

Generally okay, Clean but property could use some upgrade

6

ANNE

9 Sept 2024

·

Stayed 2 nights

rugs are so stained and worn that they appear to not be clean even if they've been shampoo'd. Woodwork is grimy with dirt no dressers available although there was plenty of room for at least 2 there is no counter space in the bathroom The desk staff was very responsive and pleasant, and the restaurant, the view, and the marina are all really excellent

2

cecilia

28 Sept 2024

·

Stayed 1 night

Not clean sheets were damp terrible experience

6

George

16 Sept 2024

·

Stayed 1 night

Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.

10

Christina

2 Jun 2025

·

Stayed 1 night

Absolutely loved our stay here! The staff were so kind and accommodating. The room was very clean and bed was comfortable. Jellee Fish Joel's (the beach bar) just received a huge makeover and we had a blast! we will be back again soon!

10

Melissa

5 Sept 2025

·

Stayed 1 night

Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!

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AI-generated summary based on recent guest reviews

Rooms

Rooms tend to be dated and small with minimal storage or in-room amenities (e.g., no closet/dresser), and some mention hard beds or pillows. Others liked comfortable beds and water views, though door slams and rattling windows created noise for a few.

Related guest reviews

2

N. Kevin

6 Oct 2024

·

Stayed 3 nights

This hotel was not as advertised. We walked into room and it was like a broke down motel. There was someone’s hair all over the bed. No closet. Bathroom I think was the closet. We informed the front desk and We left immediately How do I get a refund.

8

Charles

8 Nov 2025

·

Stayed 1 night

Beautiful view

10

Stephania

5 Nov 2025

·

Stayed 1 night

Very nice rooms,

8

Mary Beth

13 Oct 2024

·

Stayed 1 night

The hotel was functional but a bit high priced for older facility, and small rooms.

2

Peter

30 Sept 2024

·

Stayed 1 night

It would be great if one was into complete minimalistic accommodations. No decent chair to sit in. No dresser to store clothing. No closet, jus an unsightly pole in corner to hang clothes on. Bed frame that sticks out beyond the mattress to bang your shins on. Terrible bedside lighting. Single coffee pot in the hall for use by all the residents with room door unable to be propped open so you can carry 2 cups of coffee back to the room. This is a prime example of a cost cutting interior that neither the designer nor management has spent any overnight time in.

6

George

16 Sept 2024

·

Stayed 1 night

Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.

6

Tami

3 Oct 2024

·

Stayed 1 night

Hotel is very outdated, beds are hard as a rock!

8

Julie

8 Sept 2024

·

Stayed 1 night

This property is just fine for a 1-2 night stay. The rooms aren't equipped with amenities needed to make a longer stay comfortable.

6

Kait

20 Nov 2025

·

Stayed 2 nights

Felt less up to date than pictured

8

Luca

6 Oct 2023

·

Stayed 2 nights

The place is beautiful. The rooms are little small and could use updating. When I turned the air on the windows rattled so loud. I had to keep it on low to avoid the noise. No microwave in the room and be prepared for the slamming door at 6am. Other than those things we really enjoyed our time.

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AI-generated summary based on recent guest reviews

Service

Many describe staff as friendly, welcoming, and helpful with check-in issues. However, some guests struggled to reach staff or found limited availability, and a few noted no housekeeping.

Related guest reviews

10

Helen

2 Sept 2024

·

Stayed 2 nights

Stay was great. Loved the bands and bars. It would be nice if we didn’t have to drive 10 miles for breakfast. Eric is fantastic. Did not know golf was free. ( next time will bring clubs)Is there a website? We got all info from Hotels.com. All staff were extremely friendly and helpful.

8

Michael

26 Aug 2024

·

Stayed 2 nights

I was a first time visitor and was a bit disappointed when I received a phone call the morning of my arrival about the pool area being closed. The pool and the Tiki bar was all I had heard from others that I traveled with. I feel like I didn't get the full Great Oak Landing experience. with saying that the food at the restaurant was excellent and the staff were friendly and helpful, shoutout to Eden (barmaid) and Johnny who worked on the grounds and was very helpful with information.

6

ANNE

9 Sept 2024

·

Stayed 2 nights

rugs are so stained and worn that they appear to not be clean even if they've been shampoo'd. Woodwork is grimy with dirt no dressers available although there was plenty of room for at least 2 there is no counter space in the bathroom The desk staff was very responsive and pleasant, and the restaurant, the view, and the marina are all really excellent

6

George

16 Sept 2024

·

Stayed 1 night

Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.

10

Francis

28 Jul 2025

·

Stayed 1 night

Staff was very helpful in dealing with some confusion at check in. Every on went above and beyond to deal with the situation and was very welcoming during the process.

2

George

27 Sept 2025

·

Stayed 1 night

Reserved 2 rooms but only given code for one. No staff on property or reachable by phone to address situation. Waiting around and hoping for the best. And it smells bad and WiFi doesn’t work.

10

Christina

2 Jun 2025

·

Stayed 1 night

Absolutely loved our stay here! The staff were so kind and accommodating. The room was very clean and bed was comfortable. Jellee Fish Joel's (the beach bar) just received a huge makeover and we had a blast! we will be back again soon!

10

Melissa

5 Sept 2025

·

Stayed 1 night

Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!

2

Thomas

29 Sept 2024

·

Stayed 1 night

This property is not being maintained at all. Staff work limited hours. Ice machine broken, coke machine removed, only coffee option is a communal K cup machine in the hallway. Water not available to refill it.

2

Teri

29 Sept 2024

·

Stayed 2 nights

The room was clean although it smelled like an old campground. The location is very remote and has little to no security. I would not recommend staying here alone if you are a woman. The front desk closes at 6pm. Anyone can enter the lodge at any time. The stairwells and halls are not secured. The doors have digital locks, but can only be secured from the inside with a chain latch. My daughter and I did not feel safe. Especially coming in after dark. We decided not to stay.

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AI-generated summary based on recent guest reviews

Location

Waterfront marina location offers pretty views, sunsets, and a quiet, remote feel with a private beach. Some guests found approach roads bumpy and the property isolated.

Related guest reviews

8

Charles

8 Nov 2025

·

Stayed 1 night

Beautiful view

6

John

16 Jun 2025

·

Stayed 1 night

Other properties we looked for at same price points had better/newer amenities. The approach roads were really bumpy which pained my wife who has arthritis. Golf course was well kept. Maybe the grounds keeper should manage the lodge facilities? 😎

8

Camille

26 Jul 2024

·

Stayed 2 nights

Great sunsets!

8

Philip

15 Jul 2025

·

Stayed 1 night

Great place to get some quiet rest by the water

10

Cheryl

26 Jul 2024

·

Stayed 2 nights

The Marina and taking a walk along the Chesepeake Bay seeking bay glass

10

Sharon

22 Sept 2024

·

Stayed 2 nights

My only complaint is hard pillows. Loved the surroundings and wish we had more time there.

10

Michelle

5 Aug 2024

·

Stayed 2 nights

Nice weekend getaway, friendly staff and good restaurant on premises. Great beach and marina location.

10

KEVIN

23 Sept 2024

·

Stayed 2 nights

Beautiful views, easy check in and safe, quiet area and the restaurant's food was on point and we loved the live band on Saturday night!! #shawnwasagreatcook #angelawasaexcellentwaitress

10

Ashley

16 Aug 2025

·

Stayed 1 night

Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site.

2

Teri

29 Sept 2024

·

Stayed 2 nights

The room was clean although it smelled like an old campground. The location is very remote and has little to no security. I would not recommend staying here alone if you are a woman. The front desk closes at 6pm. Anyone can enter the lodge at any time. The stairwells and halls are not secured. The doors have digital locks, but can only be secured from the inside with a chain latch. My daughter and I did not feel safe. Especially coming in after dark. We decided not to stay.

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AI-generated summary based on recent guest reviews

Dining

Food at the on-site restaurant and beach bar is often praised, with occasional live music. Availability can vary, with reports of closures, no on-site breakfast, and coffee limited to communal stations.

Related guest reviews

10

Helen

2 Sept 2024

·

Stayed 2 nights

Stay was great. Loved the bands and bars. It would be nice if we didn’t have to drive 10 miles for breakfast. Eric is fantastic. Did not know golf was free. ( next time will bring clubs)Is there a website? We got all info from Hotels.com. All staff were extremely friendly and helpful.

10

Melissa

14 Jul 2024

·

Stayed 2 nights

Wonderful weekend on a girls trip, rooms were clean with great ac! We loved Michelle at the pool bar, she makes delicious frozen drinks! All of our food was delicious at the restaurant too. Not crowded and all staff was extremely nice!

10

Gaines

22 Jun 2025

·

Stayed 1 night

not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd

4

Pam

3 Nov 2024

·

Stayed 2 nights

We felt like we overpaid for what we got. Restaurant was not open. We were given 1 large towel and the rest were small. We did not have any maid service. The ice machine did not work. The coffee machine did not work. Beautiful marina. We felt like the only ones there.

8

Michael

26 Aug 2024

·

Stayed 2 nights

I was a first time visitor and was a bit disappointed when I received a phone call the morning of my arrival about the pool area being closed. The pool and the Tiki bar was all I had heard from others that I traveled with. I feel like I didn't get the full Great Oak Landing experience. with saying that the food at the restaurant was excellent and the staff were friendly and helpful, shoutout to Eden (barmaid) and Johnny who worked on the grounds and was very helpful with information.

6

George

16 Sept 2024

·

Stayed 1 night

Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.

10

Michelle

5 Aug 2024

·

Stayed 2 nights

Nice weekend getaway, friendly staff and good restaurant on premises. Great beach and marina location.

10

KEVIN

23 Sept 2024

·

Stayed 2 nights

Beautiful views, easy check in and safe, quiet area and the restaurant's food was on point and we loved the live band on Saturday night!! #shawnwasagreatcook #angelawasaexcellentwaitress

10

Melissa

5 Sept 2025

·

Stayed 1 night

Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!

10

Ashley

16 Aug 2025

·

Stayed 1 night

Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site.

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AI-generated summary based on recent guest reviews

Su	Mo	Tu	We	Th	Fr	Sa
1	2	3	4	5	6	7
8	9	10 $120	11 $124	12 $124	13 $137	14 $133
15 $109	16 $120	17 $124	18 $124	19 $124	20 $145	21 $150
22 $124	23 $124	24 $124	25 $120	26 $124	27 $145	28 $150
29 $120	30 $124

The Lodge at Great Oak Landing

About this property

Location

Room options

Room, 2 Queen Beds, Marina View

Room, 1 Queen Bed, Accessible

Standard Room, 1 King Bed

Room, 1 King Bed

Standard Room, 2 Double Beds

Room, 1 King Bed with Sofa Bed, Marina View

Suite

Guest reviews of The Lodge at Great Oak Landing

What guests think

Property policies

Check-in instructions

Good to know

FAQs about The Lodge at Great Oak Landing

Prices for upcoming dates