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The Lodge at Great Oak Landing

3.5 star property
3.5-star beach lodge with 3 bars/lounges

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Photo gallery for The Lodge at Great Oak Landing

Private beach nearby, sun loungers, beach volleyball
Point of interest
Room, 1 King Bed with Sofa bed, Marina View
Private beach nearby, sun loungers, beach volleyball
Point of interest

Reviews

7.8 out of 10
Good

Popular amenities

  • Bar
  • Pool
  • Gym
  • Laundry
  • Air conditioning
  • Free WiFi

Explore the area

View in a map
22170 Great Oak Landing Rd, Chestertown, MD, 21620
  • Place, Washington College
    ‪19 min drive‬
  • Place, River Arts Chestertown
    ‪20 min drive‬
  • Place, Historical Society of Kent County Maryland
    ‪20 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪107 min drive‬

Room options

View all photos for Room, 2 Queen Beds, Marina View

Room, 2 Queen Beds, Marina View

Room, 2 Queen Beds, Marina View

8.8 out of 10
Excellent
(3 reviews)
  • 1 bedroom
  • Water view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Standard Room, 1 King Bed

  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Room, 1 King Bed with Sofa bed, Marina View

Room, 1 King Bed with Sofa bed, Marina View

Room, 1 King Bed with Sofa bed, Marina View

10.0 out of 10
Exceptional
(2 reviews)
  • 1 bedroom
  • Water view
  • Sleeps 3
  • 1 King Bed and 1 Twin Sofa Bed

View all photos for Standard Room, 2 Double Beds

Standard Room, 2 Double Beds

Standard Room, 2 Double Beds

  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Room, 1 Queen Bed, Accessible

Room, 1 Queen Bed, Accessible

Room, 1 Queen Bed, Accessible

  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite

Suite | Balcony view

Suite

8.0 out of 10
Very good
(1 review)
  • 1 bedroom
  • Marina view
  • Sleeps 5
  • 1 King Bed, 1 Twin Sofa Bed and 1 Double Sofa Bed

View all photos for Room, 1 King Bed

Room, 1 King Bed

Room, 1 King Bed

9.0 out of 10
Wonderful
(2 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

About the area

Chestertown

Walk to the beach.At this Chestertown lodge, you'll be within 9 miles (15 km) of Washington College and 12 miles (20 km) of Garfield Center for the Arts at the Prince Theater. The Mainstay is within 16 miles (25 km) and Church Hill Theatre is within 20 miles (32 km).
View more Lodges in ChestertownOpens in a new window

What's nearby

  • Washington College - 19 min drive - 17.7 km
  • River Arts Chestertown - 20 min drive - 19.0 km
  • Wilmer Park - 20 min drive - 19.4 km
  • Historical Society of Kent County Maryland - 20 min drive - 19.4 km
  • Chestertown Historic District - 20 min drive - 19.4 km

Getting around

  • Baltimore Washington Intl. Airport (BWI) - 101 min drive

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Tolchester Marina Beach Bar - ‬25 min drive
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪Table - ‬17 min walk
  • ‪Chestertown Cooking Company - ‬29 min drive

About this property

The Lodge at Great Oak Landing

3.5-star beach lodge with 3 bars/lounges
Unwind on the private sand beach, located just 0.25 miles away. Summer fun is a breeze at The Lodge at Great Oak Landing, where you can play a round of golf at the golf course and enjoy amenities like a seasonal outdoor pool and a 24-hour fitness center.

There's a restaurant on site. You can unwind with a drink at one of the 3 bars/lounges. WiFi is free in public spaces. Free self parking is available.

This 3.5-star Chestertown lodge is smoke free.

  • 26 guestrooms or units
  • 3 bars or lounges
  • Beach lounge chairs
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Coffee in lobby
  • Self-service laundry
  • BBQ grill(s)
  • Outdoor picnic space
  • Gift shop
  • ATM
  • No smoking on site
  • Dining venue
The Lodge at Great Oak Landing offers 26 accommodations with hair dryers. 36-inch flat-screen televisions come with cable channels. Guests can surf the web using the complimentary wireless Internet access (speed: 25+ Mbps). Housekeeping is provided on request.

Similar properties

Lobby
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
4.3 out of 5, Excellent, 858 reviews
The price is CA $142
CA $158 total
includes taxes & fees
Dec 28 - Dec 29
Comfort Inn & Suites Chestertown

Property amenities

Family friendly

  • Fenced pool
  • Laundry facilities
  • Playground
  • Pool gate
  • Seasonal outdoor pool

Internet

  • Available in all rooms: Free WiFi
  • In-room WiFi speed: 25+ Mbps
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free uncovered self parking on site
  • Wheelchair-accessible parking available

Food and drink

  • 3 bars/lounges
  • A restaurant
  • Coffee and tea in common areas

Things to do

  • 24-hour gym
  • 9-hole golf course
  • Beach volleyball
  • Playground
  • Seasonal outdoor pool

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • 2 accessible parking spaces
  • Front entrance ramp
  • Upper floors accessible by stairs only
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible registration desk (32 inches high)
  • Wheelchair-accessible restaurant

Room amenities

Entertainment

  • 36-inch flat-screen TV with cable channels

Bedroom

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

More

  • Air conditioning (climate-controlled)
  • Connecting rooms available
  • Heating (climate-controlled)
  • Phone

Policies

Check-in

Check-in start time: 3:00 PM; Check-in end time: anytime
Contactless check-in available
Minimum check-in age: 21

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

The front desk is open Monday - Sunday (8:30 AM - 4:00 PM)
Guests will receive an email within 48 hours before arrival with check-in instructions and an access code; front desk staff will greet guests on arrival at the property
Information provided by the property may be translated using automated translation tools

Renovations and closures

The following facilities are closed seasonally each year. They will be closed from September 16 to May 23:
  • Bar/Lounge
  • Swimming pool
The property is closed: Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day.
The following facilities are closed on Monday, Tuesday, Wednesday, and Thursday:
  • Bar/lounge
  • Dining venue(s)

Access methods

Access code, staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cribs (infant beds) are not available.

Property payment types

Important information

You need to know

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, debit cards, and cash
Cashless transactions are available
Noise-free guestrooms cannot be guaranteed
Safety features at this property include a smoke detector and outdoor lighting
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. 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. This property accepts Visa, Mastercard, American Express, Discover, debit cards, and cash. Noise-free guestrooms cannot be guaranteed. For guests' safety, the property includes a smoke detector and outdoor lighting in each accommodation. Cashless payment methods are available for all transactions.

We should mention

  • The seasonal pool will open May 23 and close September 18.
  • Pool access available from 10:00 AM to 8:00 PM.
  • Registered guests are the only ones allowed to be in guestrooms.
  • Connecting/adjoining rooms are subject to availability and can be requested by contacting the property at the number on your booking confirmation.
  • This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).

Property is also known as

The At Great Oak Landing

The Lodge at Great Oak Landing Reviews

Reviews

7.8

Good

Rating 10 - Excellent. 38 out of 77 reviews
Rating 8 - Good. 14 out of 77 reviews
Rating 6 - Okay. 11 out of 77 reviews
Rating 4 - Poor. 5 out of 77 reviews
Rating 2 - Terrible. 9 out of 77 reviews

8.6/10

Cleanliness

8.6/10

Staff & service

7.6/10

Amenities

7.6/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

8/10 Good

Charles

Travelled with partner
Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view
Stayed 1 night in Nov 2025

10/10 Excellent

Melissa

Travelled with group
Liked: Amenities
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!!
Stayed 1 night in Sep 2025

6/10 Okay

Jennifer

Outdated. Room had a peculiar odor.
Stayed 1 night in Aug 2025

2/10 Terrible

Bely

Travelled with family and small children
Liked: Cleanliness, staff & service
Stayed 1 night in Aug 2025

6/10 Okay

jamie

Travelled with group
Liked: Cleanliness
Considering the time of year, I expected it to be a bit pricey, but I thought that the room and amenities would be better considering the price
Stayed 1 night in Aug 2025

2/10 Terrible

Todd

Disliked: Cleanliness, staff & service, property conditions & facilities

Dirty and gross

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.
Stayed 1 night in Aug 2025

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Aug 2025

10/10 Excellent

Ashley

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Aug 2025

10/10 Excellent

Mark

Liked: Cleanliness, amenities
They've definitely spent a lot of money.
Stayed 1 night in Aug 2025

10/10 Excellent

Bob

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2025

10/10 Excellent

Francis

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Great staff

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.
Sunset over the marina
Stayed 1 night in Jul 2025

10/10 Excellent

Eileen

Stayed 1 night in Jul 2025

10/10 Excellent

Wendy

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in May 2025

10/10 Excellent

Stephen

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Getaway

We love this place….awesome pool,and free golf….couldn’t ask for more 😃
Stayed 3 nights in Jul 2025

8/10 Good

Philip

Liked: Cleanliness, staff & service, property conditions & facilities
Great place to get some quiet rest by the water
Stayed 1 night in Jul 2025

10/10 Excellent

Gaines

Travelled with family
Liked: Cleanliness, property conditions & facilities
not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd
Stayed 1 night in Jun 2025

6/10 Okay

John

Travelled with partner
Liked: Cleanliness, staff & service
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? 😎
Stayed 1 night in Jun 2025

10/10 Excellent

Shannon

Stayed 1 night in Jun 2025

10/10 Excellent

Christina

Travelled with family, Travelled with family and small children
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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!
Stayed 1 night in May 2025

10/10 Excellent

Keith

Stayed 1 night in Apr 2025

10/10 Excellent

ashley

Travelled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Wonderful quiet place. Enjoyed our night.
Stayed 1 night in Apr 2025

6/10 Okay

Anna

Travelled with partner
Liked: Cleanliness, staff & service
.
Stayed 2 nights in Apr 2025

4/10 Poor

Larry, Ocean View

Stayed 1 night in Oct 2024

4/10 Poor

Pam

Travelled with group
Disliked: Staff & service
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.
Stayed 2 nights in Nov 2024

8/10 Good

Paul

Travelled with group
Liked: Cleanliness, staff & service, room comfort

Respite

Generally okay, Clean but property could use some upgrade
Stayed 1 night in Oct 2024