The Lodge at Great Oak Landing

Property class: 3.5

Choose dates to view prices

Consider a stay at The Lodge at Great Oak Landing and take advantage of a golf course, a firepit, and a playground. With a nearby private beach, beachfront dining, and sun loungers, this lodge is the perfect place to soak up some sun. Be sure to enjoy lunch, dinner, and light fare at the two on-site restaurants. Enjoy the 24-hour gym, as well as activities like beach volleyball. Free in-room WiFi, with speed of 25+ Mbps, is available to all guests, along with laundry facilities and an outdoor entertainment area.

Reviews

8.0 out of 10
Very good

Popular amenities

  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
The current price is ￥16,843
￥19,258 total
includes taxes & fees
Sep 23 - Sep 24

Room options

Available filters for rooms
Showing 7 of 7 rooms

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

8.6 out of 10
Excellent
(7 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

  • 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
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About the neighborhood

Located in Chestertown, The Lodge at Great Oak Landing is in a rural area and on the waterfront. The area's natural beauty can be seen at Eastern Neck National Wildlife Refuge, while The Mainstay and Church Hill Theatre are cultural highlights. Washington College is another place to visit that comes recommended. Visit our Chestertown travel guide
View more Lodges in Chestertown
Map
21620, MD, Chestertown, 22170 Great Oak Landing Rd

What's nearby

  • A field of soybeans with a barn and silos in the background.
    Washington College
    19 min drive - 18.0 km
  • River Arts Chestertown
    20 min drive - 19.4 km
  • Chestertown Historic District
    20 min drive - 19.7 km
  • Historical Society of Kent County Maryland
    20 min drive - 19.7 km
  • Wilmer Park
    20 min drive - 19.7 km

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

  • Lodge near Chesapeake Bay
  • 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, beachfront dining, and sun loungers. Be sure to enjoy lunch, dinner, and light fare at the two on-site restaurants. Enjoy the 24-hour gym, as well as activities like beach volleyball. 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 along with sun loungers and pool umbrellas
    • Free self parking
    • Outdoor furniture, a gift shop, and a dock
    • Charcoal grills, smoke-free premises, and ATM/banking services
  • 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

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8.6 out of 10, Excellent, 982 reviews
The price is ￥16,818
￥18,668 total
includes taxes & 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

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)

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 Sep 19, 2026, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Sep 23, 2026 start from ￥16,843, 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?

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 20 mi (32 km) of The Mainstay and Church Hill Theatre. Eastern Neck National Wildlife Refuge is 18.1 mi (29.1 km) away.

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

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Reviews

The Lodge at Great Oak Landing Reviews

8.0

Very Good

8.8

Cleanliness

7.8

Amenities

8.6

Staff & service

8.0

Property conditions & facilities
Rating 10 - Excellent. 54 out of 110 reviews
Rating 8 - Good. 24 out of 110 reviews
Rating 6 - Okay. 15 out of 110 reviews
Rating 4 - Poor. 8 out of 110 reviews
Rating 2 - Terrible. 9 out of 110 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun.
Stayed 2 nights in Aug 2026
Verified review

8/10 Good

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

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

Liked: Cleanliness, property conditions & facilities
Old facility but everywhere clean. There have a private beach. It was so nice. So cute place but restaurants are closed weekday. Microwave and coffee are not in room.AC was noisy.
Stayed 2 nights in Jun 2026
Verified review

10/10 Excellent

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

8/10 Good

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

8/10 Good

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

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

10/10 Excellent

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

6/10 Okay

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

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

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

8/10 Good

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

10/10 Excellent

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

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

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

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

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

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

10/10 Excellent

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

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

8/10 Good

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
Verified review

10/10 Excellent

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
Verified review

10/10 Excellent

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

Fun girls weekend

Wonderful weekend on a girls trip, rooms were clean with great ac! We loved Michelle at the pool bar, she makes delicious frozen drinks! All of our food was delicious at the restaurant too. Not crowded and all staff was extremely nice!
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

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