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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 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 campfire in a stone fire pit by a lakeside at sunset.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

Reviews

8.0 out of 10
Very good

Popular amenities

  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
The current price is $137
$124 nightly
$137 total
Total with taxes and fees
Aug 26 - Aug 27

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

9.2 out of 10
Wonderful
(5 reviews)
  • Water view
  • 1 bedroom
  • Sleeps 4
  • 2 Queen Beds
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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

  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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
  • Free WiFi

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  • Pool
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Sep 24 - Sep 25
Total with taxes and fees
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About the neighborhood

Chestertown

With a stay at The Lodge at Great Oak Landing in Chestertown, you'll be 8.8 mi (14.2 km) from Washington College and 12.5 mi (20.1 km) from The Mainstay. .This beach lodge is 16.9 mi (27.2 km) from Church Hill Theatre and 18.1 mi (29.1 km) from Eastern Neck National Wildlife Refuge.
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

About this property

The Lodge at Great Oak Landing

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.
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.

Stay in one of 26 guestrooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Conveniences include phones, and housekeeping is provided on request.
Practice your swing on the golf course or soak up the sunshine on the private beach. This lodge also features complimentary wireless internet access, gift shops/newsstands, and a picnic area.
Satisfy your appetite at one of the lodge's 2 restaurants. Relax with a refreshing drink at one of the 2 bars/lounges.
Featured amenities include laundry facilities, ATM/banking services, and coffee/tea in a common area. Free self parking is available onsite.
UnWined at The Cut - This beachfront bar serves light fare only. Open select days.
UnWined at Great Oak - This restaurant serves lunch and dinner. Guests can enjoy drinks at the bar. Open select days.

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 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

Pets not 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

We should mention

This property does not have elevators
The seasonal pool will be open from May 23 to September 18
Pool access available from 10:00 AM to 8:00 PM
Only registered guests are allowed in the guestrooms
The property has connecting/adjoining rooms, which are subject to availability and can be requested by contacting the property using the number on the booking confirmation
Children under 15 years old are not allowed in the swimming pool or fitness facility without adult supervision
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

8.0

Very Good

Rating 10 - Excellent. 50 out of 102 reviews
Rating 8 - Good. 21 out of 102 reviews
Rating 6 - Okay. 14 out of 102 reviews
Rating 4 - Poor. 8 out of 102 reviews
Rating 2 - Terrible. 9 out of 102 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

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

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

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
Verified review

6/10 Okay

Daniel

For the price off season the room should have had better amenities
Stayed 1 night in Oct 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….10 stars😀
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Angela

Loved the suite!! Great balcony and view!!
Stayed 2 nights in Jul 2024