See all properties

The Lodge at Great Oak Landing

3.5 star property

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

Reviews

7.8 out of 10
Good

Popular amenities

  • Bar
  • Pool
  • Gym
  • Laundry
  • Air conditioning
  • Free WiFi
$163
includes taxes & fees
Oct 2 - Oct 3

Explore the area

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

Room options

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 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 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 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 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

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

Similar properties

Lobby

Comfort Inn & Suites Chestertown

  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 825 reviews
Comfort Inn & Suites Chestertown

About this property

The Lodge at Great Oak Landing

3.5-star Chestertown lodge with golf course
Catch some rays on The Lodge at Great Oak Landing's private sand beach, practice your swing at the onsite golf course, or enjoy volleyball. Housekeeping is available on request.
The Lodge at Great Oak Landing offers 29 accommodations with hair dryers. 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.
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.

Unwind on the private sand 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 like a seasonal outdoor pool and a 24-hour fitness center.

The lodge offers a restaurant. Guests can unwind with a drink at one of the lodge's 3 bars/lounges. Wireless Internet access is complimentary. Complimentary uncovered self parking is available on site.

The Lodge at Great Oak Landing is a smoke-free property.

Fairlee's - Onsite restaurant. Guests can enjoy drinks at the bar.

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

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

Reviews

The Lodge at Great Oak Landing Reviews

7.8

Good

8.6/10

Cleanliness

8.6/10

Staff & service

7.6/10

Amenities

7.6/10

Property conditions & facilities

8.2/10

Eco-friendliness
Rating 10 - Excellent. 35 out of 70 reviews
Rating 8 - Good. 13 out of 70 reviews
Rating 6 - Okay. 9 out of 70 reviews
Rating 4 - Poor. 5 out of 70 reviews
Rating 2 - Terrible. 8 out of 70 reviews

Reviews

10/10 Excellent

Gaines

Traveled 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

Traveled 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

Traveled with family and small children, Traveled with family
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

Traveled 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

Traveled 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

Traveled 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

Traveled 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

10/10 Excellent

KRISTIAN

Stayed 2 nights in Oct 2024

2/10 Terrible

N. Kevin

Traveled with family
Disliked: Cleanliness, amenities, property conditions & facilities
This hotel was not as advertised. We walked into room and it was like a broke down motel. There was someone’s hair all over the bed. No closet. Bathroom I think was the closet. We informed the front desk and We left immediately How do I get a refund.
Stayed 3 nights in Sep 2024

4/10 Poor

Ed

Liked: Cleanliness
Disliked: Staff & service, property conditions & facilities, room comfort

Outta here!

At first I couldn't identify the smell but after an hour, I realized it was the scent of abandonment and isolation. The room was clean but everything was very basic. There was a TV but apparently no free programming. This, combined with spotty internet service and just a sense of creepiness led me to flee before dark.
Stayed 2 nights 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

10/10 Excellent

Kimberly

Business traveler
Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Stayed 1 night in Oct 2024

2/10 Terrible

Peter

Traveled with partner
Disliked: Amenities
It would be great if one was into complete minimalistic accommodations. No decent chair to sit in. No dresser to store clothing. No closet, jus an unsightly pole in corner to hang clothes on. Bed frame that sticks out beyond the mattress to bang your shins on. Terrible bedside lighting. Single coffee pot in the hall for use by all the residents with room door unable to be propped open so you can carry 2 cups of coffee back to the room. This is a prime example of a cost cutting interior that neither the designer nor management has spent any overnight time in.
Stayed 1 night in Sep 2024

10/10 Excellent

mark

Traveled with family
Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 2 nights in Sep 2024

8/10 Good

Marion

Traveled with partner
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

2/10 Terrible

Thomas

Disliked: Cleanliness, staff & service, property conditions & facilities
This property is not being maintained at all. Staff work limited hours. Ice machine broken, coke machine removed, only coffee option is a communal K cup machine in the hallway. Water not available to refill it.
Stayed 1 night in Sep 2024

4/10 Poor

Kimberly

Disliked: Amenities
Stayed 2 nights in Sep 2024

2/10 Terrible

Teri

The room was clean although it smelled like an old campground. The location is very remote and has little to no security. I would not recommend staying here alone if you are a woman. The front desk closes at 6pm. Anyone can enter the lodge at any time. The stairwells and halls are not secured. The doors have digital locks, but can only be secured from the inside with a chain latch. My daughter and I did not feel safe. Especially coming in after dark. We decided not to stay.
Stayed 2 nights in Sep 2024

2/10 Terrible

cecilia

Traveled with family
Disliked: Amenities
Not clean sheets were damp terrible experience
Stayed 1 night in Sep 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

10/10 Excellent

KEVIN

Traveled with group
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