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The Lodge at Great Oak Landing

Property class: 3.5

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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 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 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 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

The Lodge at Great Oak Landing places you 8.8 mi (14.2 km) from Washington College. This 3.5-star lodge has 26 rooms and welcomes guests with 2 restaurants, a golf course, and a private beach.
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

Guests staying at The Lodge at Great Oak Landing enjoy access to a golf course, a 24-hour gym, and free WiFi in public areas. You can put free parking to good use if you drive. Other amenities at this beach lodge include a seasonal outdoor pool, coffee/tea in a common area, and laundry facilities.
36-inch flat-screen TVs come with cable channels, and guests can stay connected with free WiFi. Hair dryers and phones are also standard. Housekeeping is available on request.
Guests can play rounds at the 9-hole golf course. In addition to a seasonal outdoor pool, other recreational amenities include a 24-hour fitness center.

Children under 15 years old are not allowed in the swimming pool or fitness facility without adult supervision.

The recreational activities listed below are available either on site or nearby; fees may apply.

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8.6 out of 10, Excellent, 975 reviews
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The price is $115
Oct 4 - Oct 5
Total with taxes and fees
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Property amenities

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

Restaurants on site

  • UnWined at Great Oak
  • UnWined at The Cut

Things to do

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

Family friendly

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

Conveniences

  • ATM
  • Gift shop/newsstand
  • Laundry facilities

Guest services

  • Housekeeping (on request)

Outdoors

  • Barbecue grill
  • Beach loungers
  • Direct access to a private beach
  • Dock
  • Firepit
  • On the bay
  • Outdoor entertainment area
  • Outdoor furniture
  • Picnic area
  • Pool loungers
  • Pool umbrellas

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

More

  • Smoking not allowed

Room amenities

Bedroom

  • Bedsheets provided

Bathroom

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

Entertainment

  • 36-inch flat-screen TV with cable channels

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

  • This property doesn't allow pets

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
  • Check-in: 3:00 PM—-anytime
  • Check-out: 11:00 AM
  • Minimum check-in age: 21
Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

  • 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.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • This property accepts credit cards, debit cards, and cash.
  • Onsite safety features include a smoke detector and outdoor lighting.
  • Cashless payment methods are available for all transactions.

Additional information about polices, regulations, and more:

  • The seasonal pool is open from May 23 to September 18.
  • Pool access available from 10:00 AM to 8:00 PM.
  • Registered guests are the only ones allowed in guestrooms.
  • Connecting or adjoining rooms can be requested, but all rooms are subject to availability. Contact the property using the phone number on your booking confirmation.
  • There are no elevators.
  • No cribs or infant beds are available.
  • No rollaway or extra beds are available.
  • Noise-free rooms can't be guaranteed.
  • 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

Are free cancellation options available at The Lodge at Great Oak Landing?

The Lodge at Great Oak Landing provides free cancellation on certain room rates. For additional details, look at the cancellation policy on our site.

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

As of Sep 12, 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.

What can I see within easy reach of The Lodge at Great Oak Landing?

This lodge is located in Chestertown, close to Pooles Island Light, Kinnairds Point Drive, and Still Pond Station Park. You'll also find Chesapeake Bay and Northern Chesapeake Bay within a short drive.

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

Yes, uncovered self parking is offered for free at the lodge. Wheelchair-accessible parking is also available for guests.

Does The Lodge at Great Oak Landing have a casino?

No, The Lodge at Great Oak Landing doesn't have a casino.

Will I find an indoor pool at The Lodge at Great Oak Landing?

No, this lodge doesn't have an indoor pool; however, there is an outdoor pool. Guests have access between 10:00 AM and 8:00 PM and the seasonal pool will be open from May 23 until September 18.

Is The Lodge at Great Oak Landing a good place to stay for couples?

This waterfront lodge offers plenty of amenities for couples including a private beach (direct access), a beachfront restaurant, and 2 bars/lounges.

Does The Lodge at Great Oak Landing have a hot tub?

No, this lodge doesn't have a spa tub.

Does The Lodge at Great Oak Landing have a restaurant that serves breakfast?

No, The Lodge at Great Oak Landing doesn't have a restaurant that serves breakfast.

Will The Lodge at Great Oak Landing allow pets to stay free of charge?

No, pets aren't allowed at The Lodge at Great Oak Landing.

Does The Lodge at Great Oak Landing have connecting rooms available?

Yes, this lodge has connecting rooms you can book for your group event or vacation.

What is the closest airport to The Lodge at Great Oak Landing?

The closest major airport to The Lodge at Great Oak Landing is Baltimore, MD (MTN-Martin State), which is about 12.6 mi away. Another top airport is Baltimore Washington Intl. Airport (BWI), which is around 25.8 mi away.

Are there rooms with balconies at The Lodge at Great Oak Landing?

Yes, some guestrooms at The Lodge at Great Oak Landing offer a furnished balcony and may feature marina views.

The Lodge at Great Oak Landing Reviews

Reviews

8.0

Very Good

Rating 10 - Excellent. 53 out of 106 reviews
Rating 8 - Good. 21 out of 106 reviews
Rating 6 - Okay. 15 out of 106 reviews
Rating 4 - Poor. 8 out of 106 reviews
Rating 2 - Terrible. 9 out of 106 reviews

8.6/10

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

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

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

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