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The Lodge at Great Oak Landing

3.5 star property
Lodge with private beach, seasonal outdoor pool

Photo gallery for The Lodge at Great Oak Landing

Private beach nearby, sun-loungers, beach volleyball
Point of interest
Point of interest
Private beach nearby, sun-loungers, beach volleyball
Room, 1 King Bed with Sofa bed, Marina View

Reviews

7.8 out of 10
Good

Popular amenities

  • Pool
  • Parking included
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
  • Gym
The current price is AU$169
includes taxes & fees
4 Jan - 5 Jan 2026

Explore the area

View map
22170 Great Oak Landing Rd, Chestertown, MD, 21620
  • Place, Washington College
    ‪19 min drive‬
  • Place, River Arts Chestertown
    ‪20 min drive‬
  • Place, Historical Society of Kent County Maryland
    ‪20 min drive‬
  • Airport, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall)
    ‪107 min drive‬

Room options

View all photos for Room, 2 Queen Beds, Marina View

Room, 2 Queen Beds, Marina View

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
Hairdryer
Shower/bath combination
Private bathroom
  • 1 bedroom
  • Water view
  • Sleeps 4
  • 2 Queen Beds

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Standard Room, 1 King Bed

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Hairdryer
Shower/bath combination
Private bathroom
  • 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

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
Hairdryer
Shower/bath combination
Private bathroom
  • 1 bedroom
  • Water view
  • Sleeps 3
  • 1 King Bed and 1 Single Sofa Bed

View all photos for Standard Room, 2 Double Beds

Standard Room, 2 Double Beds

Standard Room, 2 Double Beds

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Hairdryer
Shower/bath combination
Private bathroom
  • 1 bedroom
  • Sleeps 4
  • 2 Double Beds

View all photos for Room, 1 Queen Bed, Accessible

Room, 1 Queen Bed, Accessible

Room, 1 Queen Bed, Accessible

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Hairdryer
Shower/bath combination
Private bathroom
  • 1 bedroom
  • Sleeps 2
  • 1 Queen Bed

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
Fridge
Flat-screen TV
  • 1 bedroom
  • Marina view
  • Sleeps 5
  • 1 King Bed, 1 Single Sofa Bed and 1 Double Sofa Bed

View all photos for Room, 1 King Bed

Room, 1 King Bed

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
Hairdryer
Shower/bath combination
Private bathroom
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

About the area

Chestertown

At The Lodge at Great Oak Landing, you'll be 14.2 km (8.8 mi) from Washington College and 15.5 km (9.6 mi) from Garfield Center for the Arts at the Prince Theater. Highlights at this beach lodge include 3 bars/lounges, a golf course and a nearby private beach. .Enjoy the 24-hour gym, seasonal outdoor swimming pool and pool loungers as well as access to a playground. The lodge's restaurant is a nice spot to grab a bite. Other amenities include free Wi-Fi in public areas, coffee/tea in a common area and laundry facilities. There's also the convenience of free self parking. .With a stay at this 3.5-property class Chestertown lodge, you'll be 20.1 km (12.5 mi) from The Mainstay and 27.2 km (16.9 mi) from Church Hill Theatre.
View more Lodges in ChestertownOpens in a new window

What's nearby

  • Washington College - 19 min drive - 17.7 km
  • River Arts Chestertown - 20 min drive - 19.0 km
  • Wilmer Park - 20 min drive - 19.4 km
  • Historical Society of Kent County Maryland - 20 min drive - 19.4 km
  • Chestertown Historic District - 20 min drive - 19.4 km

Getting around

  • Baltimore Washington International Airport (BWI) - 101 min drive

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Tolchester Marina Beach Bar - ‬25 min drive
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪Table - ‬17 min walk
  • ‪Chestertown Cooking Company - ‬29 min drive

About this property

The Lodge at Great Oak Landing

Lodge with private beach, seasonal outdoor pool
Unwind on the private sandy beach, located just 0.25 miles away. Summer fun is a breeze at The Lodge at Great Oak Landing, where you can play a round of golf at the golf course and enjoy amenities such as a seasonal outdoor pool and a 24-hour fitness centre.

There's a restaurant on site. You can unwind with a drink at one of the 3 bars/lounges. WiFi is free in public spaces. Free self parking is available.

This 3.5-star Chestertown lodge is smoke free.

  • 26 guestrooms or units
  • 3 bars or lounges
  • Beach lounge chairs
  • Poolside lounge chairs
  • Umbrellas for the pool
  • Coffee in lobby
  • Self-service laundry
  • BBQ grill(s)
  • Outdoor picnic space
  • Gift shop
  • ATM
  • No smoking on site
  • Dining venue
The Lodge at Great Oak Landing offers 26 accommodations with a hairdryer. 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.

Similar properties

Lobby
Comfort Inn & Suites Chestertown
  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
4.3 out of 5, Excellent, 861 reviews
The price is AU$173
includes taxes & fees
29 Dec - 30 Dec
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 transport

  • Free uncovered self parking on site
  • Limited on-site self parking
  • 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 (81 centimetre high)
  • Wheelchair-accessible restaurant

More

  • Smoke-free property

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 and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 11:00 AM
Contactless check-out

Special check-in instructions

The front desk is open Monday - Sunday (8:30 AM - 4:00 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
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 16 September to 23 May:
  • 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
  • Restaurant

Access methods

Access code, staffed front desk

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.
  • Rollaway/extra beds are not available.
  • Cots (infant beds) are not available.

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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    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 and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. This property accepts Visa, Mastercard, American Express, Discover, debit cards and cash. Noise-free guestrooms cannot be guaranteed. For guests' safety, the property includes a smoke detector and outdoor lighting in all accommodation. Cashless payment methods are available for all transactions.

We should mention

  • The seasonal pool will open on 23 May and close on 18 September.
  • Pool access available from 10:00 AM to 8:00 PM
  • Registered guests are the only ones allowed to be in guestrooms.
  • Connecting/adjoining rooms are subject to availability and can be requested by contacting the property at the number on your booking confirmation.
  • 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

What is the cancellation policy at The Lodge at Great Oak Landing?

The Lodge at Great Oak Landing offers free cancellation on select room rates. Check out the cancellation policy for more info.

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

As of 24 Dec 2025, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on 4 Jan 2026 start from AU$168.88, including 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 parking available at The Lodge at Great Oak Landing?

Yep, The Lodge at Great Oak Landing has a free self car park.

Are there any beaches close to The Lodge at Great Oak Landing?

The closest beach to The Lodge at Great Oak Landing is Miami Beach (15.3 km).

Does The Lodge at Great Oak Landing have a pool?

The Lodge at Great Oak Landing has a seasonal outdoor pool. Grab your bathers and lounge poolside while enjoying under the shade of an umbrella. The pool is open 10:00 AM to 8:00 PM (Seasonal outdoor pool open from May 23 to September 18). The swimming pool is closed on Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

Is there a free airport shuttle available at The Lodge at Great Oak Landing?

No, The Lodge at Great Oak Landing does not offer an airport shuttle service.

Is there a bar or restaurant at The Lodge at Great Oak Landing?

Yep, you can grab a meal at The Lodge at Great Oak Landing's onsite restaurant.The dining venue is closed on Monday, Tuesday, Wednesday and Thursday. The bar is closed seasonally each year from September 16 until May 23. The dining venue is closed on Christmas Eve, Christmas Day, New Year's Eve and New Year's Day.

What time are check-in & check-out at The Lodge at Great Oak Landing?

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Are pets allowed at The Lodge at Great Oak Landing?

No, pets are not allowed.

Is there a golf course on site at The Lodge at Great Oak Landing?

Yep, The Lodge at Great Oak Landing has a 9-hole golf course.

The Lodge at Great Oak Landing Reviews

Reviews

7.8

Good

Rating 10 - Excellent. 38 out of 77 reviews
Rating 8 - Good. 14 out of 77 reviews
Rating 6 - Okay. 11 out of 77 reviews
Rating 4 - Poor. 5 out of 77 reviews
Rating 2 - Terrible. 9 out of 77 reviews

8.6/10

Cleanliness

8.6/10

Staff & service

7.6/10

Amenities

7.6/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

10/10 Excellent

Melissa

Travelled with group
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

6/10 Okay

Jennifer

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

2/10 Terrible

Bely

Travelled with family and small children
Liked: Cleanliness, staff & service
Stayed 1 night in Aug 2025

6/10 Okay

jamie

Travelled with group
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

2/10 Terrible

Todd

Disliked: Cleanliness, staff & service, property conditions & facilities

Dirty and gross

Only pro was the bed was comfortable. The room was dirty and everything was old and very outdated. Floorboards, doors and fixtures were dirty. Shower floor was gross. Walls had rust, dirt and holes. Deck was unkempt and dirty. Did not eat there because I didn’t trust the cleanliness of their kitchen based on the room.
Stayed 1 night in Aug 2025

10/10 Excellent

Peter

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in Aug 2025

10/10 Excellent

Ashley

Travelled with family, Travelled with family and small children
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

Bob

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 2 nights in Aug 2025

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

10/10 Excellent

Eileen

Stayed 1 night in Jul 2025

10/10 Excellent

Wendy

Liked: Cleanliness, staff & service, property conditions & facilities
Stayed 1 night in May 2025

10/10 Excellent

Stephen

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

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

Gaines

Travelled with family
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

6/10 Okay

John

Travelled with partner
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

Shannon

Stayed 1 night in Jun 2025

10/10 Excellent

Christina

Travelled with family, Travelled with family and small children
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

10/10 Excellent

Keith

Stayed 1 night in Apr 2025

10/10 Excellent

ashley

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

6/10 Okay

Anna

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

4/10 Poor

Larry, Ocean View

Stayed 1 night in Oct 2024

4/10 Poor

Pam

Travelled with group
Disliked: Staff & service
We felt like we overpaid for what we got. Restaurant was not open. We were given 1 large towel and the rest were small. We did not have any maid service. The ice machine did not work. The coffee machine did not work. Beautiful marina. We felt like the only ones there.
Stayed 2 nights in Nov 2024

8/10 Good

Paul

Travelled with group
Liked: Cleanliness, staff & service, room comfort

Respite

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