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The Lodge at Great Oak Landing

3.5 star property
Lodge with private beach, seasonal outdoor pool

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Photo gallery for The Lodge at Great Oak Landing

Private beach nearby, sun loungers, beach volleyball
Point of interest
Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets
Point of interest
Private beach nearby, sun loungers, beach volleyball

Reviews

8.0 out of 10
Very good

Popular amenities

  • Bar
  • Pool
  • Gym
  • Laundry
  • Air conditioning
  • Free WiFi

Explore the area

View in a map
22170 Great Oak Landing Rd, Chestertown, MD, 21620
  • Washington College
    ‪23 min drive‬
  • The Mainstay
    ‪33 min drive‬
  • Rock Hall Harbor
    ‪34 min drive‬
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪127 min drive‬

Room options

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

  • 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

  • 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

  • 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)
  • 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)
  • 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)
  • 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)
  • 1 bedroom
  • Marina view
  • Sleeps 5
  • 1 King Bed, 1 Twin Sofa Bed and 1 Double Sofa Bed

About the neighborhood

Chestertown

The Lodge at Great Oak Landing places you 8.8 mi (14.2 km) from Washington College and 9.6 mi (15.5 km) from Garfield Center for the Arts at the Prince Theater. This 3.5-star lodge has 29 rooms and welcomes guests with a restaurant, a golf course, and a private beach.
View more Lodges in ChestertownOpens in a new window

What's nearby

  • Washington College - 23 min drive - 10.8 miles
  • River Arts Chestertown - 24 min drive - 11.6 miles
  • The Mainstay - 33 min drive - 14.7 miles
  • Rock Hall Harbor - 34 min drive - 15.2 miles
  • Eastern Neck National Wildlife Refuge - 44 min drive - 21.7 miles

Getting around

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

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Tolchester Marina Beach Bar - ‬25 min drive
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪Harbor House - ‬13 min drive
  • ‪Chestertown Cooking Company - ‬29 min drive

About this property

The Lodge at Great Oak Landing

Lodge with private beach, seasonal outdoor pool
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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Lobby

Comfort Inn & Suites Chestertown

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  • Breakfast included
  • Pet friendly
  • Parking included
8.6 out of 10, Excellent, 820 reviews
$112 nightly
The price is $124
Sep 28 - Sep 29
Total with taxes and fees
Comfort Inn & Suites Chestertown

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 Monday - Sunday (8:30 AM - 4:30 PM)
Front desk staff will greet guests on arrival at the property
Guests are recommended to download the property's text message mobile app before check-in

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 24, 2025, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Oct 1, 2025 start from $147.0, 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.

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.

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

Yes, uncovered self parking is offered for free at the lodge. 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 good for couples?

This waterfront lodge offers plenty of amenities for couples including 3 bars, a restaurant, and a golf course.

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?

Yes, this lodge has connecting guestrooms 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.

Can I book a room with a balcony 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.