Skip to Main Content.
List your propertySupportTrips
Member discount illustration

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Sign in
Learn about Expedia Rewards
Feedback

The Lodge at Great Oak Landing

3.5 star property
Lodge with private beach, seasonal outdoor pool

Choose dates to view prices

Photo gallery for The Lodge at Great Oak Landing

Private beach nearby, sun loungers, beach volleyball
Private beach nearby, sun loungers, beach volleyball
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
Point of interest
Point of interest
Nestled on the waterfront, The Lodge at Great Oak Landing offers a serene retreat with a private beach and sun loungers. Enjoy golfing, sipping cocktails at the poolside bar or simply unwind by the firepit. With free in-room WiFi, express check-out and charcoal grills available.

Reviews

8.0 out of 10
Very good

Popular amenities

  • Bar
  • Gym
  • Pool
  • Laundry
  • Air conditioning
  • Free WiFi
The current price is ￥19,440
￥21,578 total
includes taxes & fees
Aug 27 - Aug 28
Private beach nearby, sun loungers, beach volleyball

Near the beach

This lodge is located on the waterfront and offers direct access to a private beach 0.25 miles away. Take advantage of the beach loungers at the sandy beach. An on-site activity to enjoy while visiting is beach volleyball.

Beach bar
What guests liked about the beach

The property offers a private beach with comfortable amenities, including chairs and umbrellas.

Room options

Available filters for rooms
Showing 7 of 7 rooms

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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 1 bedroom
  • Sleeps 2
  • 1 King 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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 1 bedroom
  • Sleeps 2
  • 1 Queen 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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 1 bedroom
  • Water view
  • Sleeps 3
  • 1 King Bed and 1 Twin Sofa Bed

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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/tub combination
Private bathroom
Hair dryer
  • 1 bedroom
  • Water view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Suite

Suite | Balcony view

Suite

8.0 out of 10
Very good
(1 review)

Highlights

Furnished balcony
Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Refrigerator
Flat-screen TV
  • 1 bedroom
  • Marina view
  • Sleeps 5
  • 1 King Bed, 1 Twin Sofa Bed and 1 Double Sofa Bed
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!
Sign inSign up, it's free

About the neighborhood

Map
21620, MD, Chestertown, 22170 Great Oak Landing Rd

What's nearby

  • Washington College - 23 min drive - 17.3 km
  • River Arts Chestertown - 24 min drive - 18.7 km
  • The Mainstay - 33 min drive - 23.7 km
  • Rock Hall Harbor - 34 min drive - 24.4 km
  • Eastern Neck National Wildlife Refuge - 44 min drive - 34.9 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
  • ‪Unruh's Carryout - ‬21 min drive
  • ‪Chestertown Cooking Company - ‬29 min drive
  • ‪Harbor House Restaurant - ‬12 min drive

About this property

The Lodge at Great Oak Landing

Lodge on the waterfront
Take advantage of a golf course, a firepit, and a playground at The Lodge at Great Oak Landing. This lodge is a great place to bask in the sun with a nearby private beach, sun loungers, and beach volleyball. Be sure to enjoy a meal at Fairlee's, the on-site restaurant. Free in-room WiFi, with speed of 25+ Mbps, is available to all guests, along with laundry facilities and an outdoor entertainment area.
You'll also enjoy perks such as:
  • A seasonal outdoor pool with sun loungers and pool umbrellas
  • Free self parking
  • Charcoal grills, outdoor furniture, and a dock
  • ATM/banking services, a gift shop, and coffee/tea in the lobby
Room features
All guestrooms at The Lodge at Great Oak Landing feature comforts such as air conditioning, in addition to amenities like free WiFi.
Extra amenities include:
  • Bathrooms with hair dryers and shampoo
  • 36-inch flat-screen TVs with cable channels
  • Heating, housekeeping, and phones

Languages

English

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

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

Restaurants on site

  • Fairlee's

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)
Front desk staff will greet guests on arrival at the property

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

Frequently asked questions

Does The Lodge at Great Oak Landing have a pool?

Yes, this property has a seasonal outdoor pool. Pool access is from 10:00 AM–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.

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

As of Aug 26, 2025, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Aug 27, 2025 start from ￥19,440, 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.

Is The Lodge at Great Oak Landing pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Lodge at Great Oak Landing?

Self parking is free at this property.

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

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

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

Check-out is at 11:00 AM.

Where is The Lodge at Great Oak Landing located?

Offering direct access to the beach, this Chestertown lodge is 8.8 mi (14.2 km) from Washington College and within 16 mi (25 km) of Garfield Center for the Arts at the Prince Theater and The Mainstay. Church Hill Theatre and Eastern Neck National Wildlife Refuge are also within 20 mi (32 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

The Lodge at Great Oak Landing Reviews

Reviews

8.0

Very Good

Rating 10 - Excellent. 33 out of 66 reviews
Rating 8 - Good. 13 out of 66 reviews
Rating 6 - Okay. 9 out of 66 reviews
Rating 4 - Poor. 4 out of 66 reviews
Rating 2 - Terrible. 7 out of 66 reviews

8.6/10

Cleanliness

8.8/10

Staff & service

7.4/10

Amenities

7.6/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

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

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

10/10 Excellent

Mark

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

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

10/10 Excellent

ashley

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

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

6/10 Okay

Jennifer

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

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

6/10 Okay

John

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

Susan

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

8/10 Good

Camille

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

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

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

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities
The room was very clean and comfortable. No frills but perfect for our overnight stay. The view from the queen bed room was lovely. The waitress at the restaurant was exceptional and the food was delicious and hot. We enjoyed the private beach and the areas to walk around the marina.
Stayed 1 night in Sep 2024

6/10 Okay

Anna

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

10/10 Excellent

Angela

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

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

8/10 Good

Marion

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great stay. Season was ending soon but bubbler was empty and not refilled, Keurig in the hall convenient but would be nice to have better creamers available in the room and water at the keurig stations refilled.
Stayed 1 night in Sep 2024

10/10 Excellent

Sharon

Liked: Cleanliness, staff & service, property conditions & facilities
My only complaint is hard pillows. Loved the surroundings and wish we had more time there.
Stayed 2 nights in Sep 2024

10/10 Excellent

Cheryl

The Marina and taking a walk along the Chesepeake Bay seeking bay glass
Stayed 2 nights in Jul 2024

8/10 Good

Mary Beth

Over prived

The hotel was functional but a bit high priced for older facility, and small rooms.
Stayed 1 night in Oct 2024

6/10 Okay

Tami

Liked: Staff & service
Disliked: Property conditions & facilities
Hotel is very outdated, beds are hard as a rock!
Stayed 1 night in Aug 2024

8/10 Good

Paul

Liked: Cleanliness, staff & service, room comfort

Respite

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

10/10 Excellent

Helen

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stay was great. Loved the bands and bars. It would be nice if we didn’t have to drive 10 miles for breakfast. Eric is fantastic. Did not know golf was free. ( next time will bring clubs)Is there a website? We got all info from Hotels.com. All staff were extremely friendly and helpful.
Stayed 2 nights in Aug 2024

6/10 Okay

George

Liked: Amenities
Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.
Stayed 1 night in Sep 2024