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The Lodge at Great Oak Landing

Property class: 3.5
3.5-star beach lodge near Chesapeake Bay

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Photo gallery for The Lodge at Great Oak Landing

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

Reviews

8.0 out of 10
Very good

Popular amenities

  • 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, River Arts Chestertown
    ‪20 min drive‬
  • Place, Chestertown Historic District
    ‪20 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪127 min drive‬

Room options

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

A hotel room with two beds, a wooden headboard, a nightstand, a lamp, a painting, and a window with curtains.

Room, 2 Queen Beds, Marina View

9.4 out of 10
Exceptional
(6 reviews)
  • Water view
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 King Bed

A hotel room with a bed, a desk, a chair, a window with curtains, a wall-mounted TV, a painting, and a floor lamp.

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

A hotel room with a bed, a desk, a chair, a window with curtains, and artwork on the walls.

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

A hotel room with two beds, a wooden headboard, a desk with a lamp, a chair, and a window with curtains.

Standard Room, 2 Double Beds

7.0 out of 10
Good
(4 reviews)
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Room, 1 Queen Bed, Accessible

A hotel room with a bed, a chair, a table with a basket, a lamp, and two paintings on the wall.

Room, 1 Queen Bed, Accessible

  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

View all photos for Suite

A marina with boats docked, surrounded by greenery and a white pergola with seating.

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

A bedroom with a bed, a desk, a TV, and a window with curtains.

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.Stay at this Chestertown lodge and you'll be within 9 miles (15 km) of Washington College and 16 miles (25 km) of The Mainstay. Church Hill Theatre and Eastern Neck National Wildlife Refuge are also within 20 miles (32 km).
View more Lodges in ChestertownOpens in a new window

What's nearby

  • Washington College - 19 min drive - 11.2 miles
  • River Arts Chestertown - 20 min drive - 12.0 miles
  • Chestertown Historic District - 20 min drive - 12.3 miles
  • Historical Society of Kent County Maryland - 20 min drive - 12.3 miles
  • Wilmer Park - 20 min drive - 12.3 miles

Getting around

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

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪Unruh's Carryout - ‬21 min drive
  • ‪Clarks Country Store - ‬18 min drive
  • ‪JR's Watermark Grille - ‬5 min walk

About this property

The Lodge at Great Oak Landing

3.5-star beach lodge near Chesapeake Bay
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 are 2 restaurants on site. You can unwind with a drink at one of the 2 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
  • 2 dining venues
  • 2 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
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
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  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 974 reviews
$104 nightly
The price is $115
Oct 4 - Oct 5
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

  • 2 bars/lounges
  • 2 restaurants
  • 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 on-site 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 Sunday - Thursday (8:30 AM - 4:30 PM) and Friday - Saturday (8:30 AM - 6:00 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

To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation

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 Sep 11, 2026, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Sep 13, 2026 start from $137, including 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?

There are 2 onsite restaurants, offering options like a beachfront location and light fare. 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

8.0

Very Good

Rating 10 - Excellent. 53 out of 105 reviews
Rating 8 - Good. 21 out of 105 reviews
Rating 6 - Okay. 14 out of 105 reviews
Rating 4 - Poor. 8 out of 105 reviews
Rating 2 - Terrible. 9 out of 105 reviews

8.8/10

Cleanliness

8.6/10

Staff & service

7.6/10

Amenities

7.8/10

Property conditions & facilities

Reviews

Verified review

8/10 Good

Nicola

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again
Stayed 1 night in May 2026
Verified review

8/10 Good

Gail

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
clean, comfortable, and staff was friendly and helpful.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Myrna

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
This property is situated in a beautiful marina with excellent facilities. Guests staying at the Lodge can also enjoy complimentary golf, which was a great bonus. We thoroughly enjoyed our stay and would happily return. The only drawback was that the Wi-Fi service was somewhat inconsistent.
Stayed 1 night in Jun 2026
Verified review

8/10 Good

Zan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
A lovely spot with views of the marina. We went in the offseason, so there were very few hotel guests and the price was extremely reasonable. Memory foam mattresses. Nothing fancy, but it had a small fridge and free coffee from a station in the hall. Note: no elevator, so if mobility is an issue, request the first floor.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Michelle

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice weekend getaway, friendly staff and good restaurant on premises. Great beach and marina location.
Stayed 2 nights in Aug 2024
Verified review

10/10 Excellent

Stephania

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

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
Verified review

8/10 Good

Charles

Liked: Cleanliness, staff & service, property conditions & facilities
Beautiful view
Stayed 1 night in Nov 2025
Verified review

6/10 Okay

Kevin

Liked: Cleanliness
There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. We made it work, we would do it again.
Stayed 2 nights in May 2026
Verified review

10/10 Excellent

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities
Very short stay but enjoyed the amenities available
Stayed 1 night in Jun 2024
Verified review

10/10 Excellent

ashley

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

10/10 Excellent

Alicia

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We arrived late Friday night. I called earlier in the day to let them know we would be late for checking. They sent a text with our room number and door code. They also called to confirm later that evening that I received the text with my information. The Lodge is older but in great shape. The location is beautiful and the marina is well taken care of.
Stayed 2 nights in Apr 2026
Verified review

10/10 Excellent

Melissa

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
Verified review

10/10 Excellent

Melissa

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay. We will be back next year.
Stayed 1 night in Jul 2024
Verified review

8/10 Good

Camille

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great sunsets!
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Gaines

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
Verified review

4/10 Poor

Mary

Liked: Cleanliness
Disliked: Amenities
I was very disappointed because the post was misleading. Nothing was open - not the bar or the pool and there was no entertainment. The post advertised a Tiki Bar, a Restaurant and a pool. None of this was open and there is a 15 minute drive to get to the nearest town. The whole point of staying there was not to have to leave the site. Dinner, music, and entertainment were advertised but I paid for a vacant facility with no food, no bar and no pool. Expedia needs to make this right!
Stayed 1 night in May 2026
Verified review

10/10 Excellent

Ashley

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
Verified review

2/10 Terrible

Barbara

I was unaware that this hotel was a seasonal place to stay. When we arrived the place was a ghosttown. The two employees i
Stayed 1 night in Dec 2025
Verified review

10/10 Excellent

Stephen

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

Great vacation

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😀
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Christina

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
Verified review

6/10 Okay

jamie

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
Verified review

10/10 Excellent

Ryon

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Absolutely gorgeous property, friendly travelers and staff! So wonderful I will be back! Thank you!
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

KEVIN

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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
Stayed 2 nights in Sep 2024
Verified review

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

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