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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

  • Pool
  • Parking included
  • Free WiFi
  • Restaurant
  • Air conditioning
  • Gym
The current price is ₩152,894
₩174,804 total
includes taxes & fees
Aug 23 - Aug 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

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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About the neighborhood

Located in Chestertown, The Lodge at Great Oak Landing is in a rural area and on the waterfront. Garfield Center for the Arts at the Prince Theater and The Mainstay are cultural highlights, and travelers looking to shop may want to visit Queenstown Premium Outlets. Washington College and Church Hill Theatre are two other places to visit that come recommended. Visit our Chestertown travel guide
View more Lodges in Chestertown
Map
22170 Great Oak Landing Rd, Chestertown, MD, 21620

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
  • Garfield Center for the Arts at the Prince Theater
    20 min drive - 19.7 km
  • Historical Society of Kent County Maryland
    20 min drive - 19.7 km

Getting around

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

Restaurants

  • Tolchester Marina Beach Bar
    25 min drive
  • Mangroves Restaurant
    5 min walk
  • Unruh's Carryout
    21 min drive
  • Chestertown Cooking Company
    29 min drive
  • Clark's Store & Laundrymat
    18 min drive

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
    • Gas grills, ATM/banking services, and a dock
    • Coffee/tea in the lobby, outdoor furniture, and a gift shop
  • 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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The price is ₩147,511
₩163,737 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 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 Aug 18, 2026, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Aug 23, 2026 start from ₩152,894, 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 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).

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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