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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
Property grounds
Point of interest
Private beach nearby, sun loungers, beach volleyball
Reception

Reviews

7.8 out of 10
Good

Popular amenities

  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym

Explore the area

View in a map
22170 Great Oak Landing Rd, Chestertown, MD, 21620
  • Place, Washington College
    ‪19 min drive‬
  • Place, Garfield Center for the Arts at the Prince Theater
    ‪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 | 1 bedroom, free WiFi, bed sheets

Room, 2 Queen Beds, Marina View

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

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | 1 bedroom, free WiFi, bed sheets

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 | 1 bedroom, free WiFi, bed sheets

Room, 1 King Bed with Sofa bed, Marina View

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

View all photos for Standard Room, 2 Double Beds

Standard Room, 2 Double Beds | 1 bedroom, free WiFi, bed sheets

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 | 1 bedroom, free WiFi, bed sheets

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)
  • Marina view
  • 1 bedroom
  • 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 | 1 bedroom, free WiFi, bed sheets

Room, 1 King Bed

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

About the neighborhood

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 - 11.0 miles
  • River Arts Chestertown - 20 min drive - 11.8 miles
  • Wilmer Park - 20 min drive - 12.1 miles
  • Garfield Center for the Arts at the Prince Theater - 20 min drive - 12.1 miles
  • Historical Society of Kent County Maryland - 20 min drive - 12.1 miles

Getting around

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

Restaurants

  • ‪Tolchester Marina Beach Bar - ‬25 min drive
  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪O'Brien Compound Maryland Edition - ‬27 min drive
  • ‪JR's Watermark Grille - ‬5 min walk

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

Free daily full breakfast
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 873 reviews
$100 nightly
The price is $111
Feb 24 - Feb 25
Total with taxes and fees
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 - Friday (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

Frequently asked questions

How close is The Lodge at Great Oak Landing to the airport?

The Lodge at Great Oak Landing is 88.1 mi (116-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

How much does it cost to stay at The Lodge at Great Oak Landing?

As of Feb 14, 2026, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Mar 2, 2026 start from $120.0, excluding taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Does The Lodge at Great Oak Landing have an airport shuttle?

Airport shuttle services are not available at The Lodge at Great Oak Landing.

How close is The Lodge at Great Oak Landing to the beach?

This lodge is 14.7 mi (31-min drive) from Betterton Beach and 14.7 mi (35-min drive) from Main Beach. Don't forget your sunscreen!

Does The Lodge at Great Oak Landing offer free breakfast?

The Lodge at Great Oak Landing does not offer free breakfast.

Is there a casino at The Lodge at Great Oak Landing?

No, there is no casino at this lodge.

What time is check-in at The Lodge at Great Oak Landing?

Check-in start time: 3:00 PM; Check-in end time: anytime.

Is there free parking at The Lodge at Great Oak Landing?

This lodge offers free self parking.

Does The Lodge at Great Oak Landing have a pool?

The Lodge at Great Oak Landing features a seasonal outdoor pool. Guests can enjoy pool access from 10:00 AM to 8:00 PM.The pool is closed seasonally each year from September 16 to May 23. The pool is closed on Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day.

Does The Lodge at Great Oak Landing have a restaurant?

Yes, there is a restaurant on site. The dining venue(s) are closed on Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day.

Does The Lodge at Great Oak Landing have a spa?

There are no spa services available at this lodge.

How close is The Lodge at Great Oak Landing to downtown Chestertown?

The Lodge at Great Oak Landing is 0.2 mi away from 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

Reviews

8/10 Good

Charles

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

10/10 Excellent

Stephania

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice rooms,
Stayed 1 night in Oct 2025

6/10 Okay

Daniel

For the price off season the room should have had better amenities
Stayed 1 night in Oct 2025

10/10 Excellent

Lauri

Stayed 1 night in Oct 2025

10/10 Excellent

Tisha

Stayed 1 night in Sep 2025

4/10 Poor

Steve

Traveled with family
Liked: Cleanliness, staff & service, room comfort
WIFI did not work. As such WIFI TV apps (Netflix, Prime, etc) were unavailable.
Stayed 1 night in Sep 2025

2/10 Terrible

George

Traveled with family
Disliked: Cleanliness, staff & service, property conditions & facilities
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.
Stayed 1 night in Sep 2025

10/10 Excellent

Melissa

Traveled 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

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

6/10 Okay

jamie

Traveled 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

Traveled with family and small children, Traveled with family
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

Traveled 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

Traveled 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

Traveled with family and small children, Traveled with family
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