Skip to main content

The Lodge at Great Oak Landing

3.5 star property
Beach lodge in Chestertown with golf course and restaurant

Choose dates to view prices

Nestled on the waterfront, The Lodge at Great Oak Landing offers a serene retreat with a private beach and sun loungers. Enjoy golfing, sipping cocktails at the poolside bar or simply unwind by the firepit. With free in-room WiFi, express check-out and charcoal grills available.

Reviews

8.0 out of 10
Very good

Popular amenities

  • Bar
  • Connecting rooms available
  • Gym
  • Pool
  • Laundry facilities
  • Air conditioning

Main amenities (12)

  • Housekeeping (on request)
  • Golf course
  • Private beach
  • Restaurant and 3 bars/lounges
  • 24-hour fitness center
  • Beach sun loungers
  • Seasonal outdoor pool
  • Coffee/tea in a common area
  • ATM/banking services
  • Self-serve laundry
  • Gift shops/newsstands
  • Picnic area

Feel at home (6)

  • Playground on site
  • Connecting/adjoining rooms available
  • Private bathroom
  • Laundry facilities
  • In-room climate control (air conditioning)
  • Cable TV service
The current price is CNY703
CNY803 total
includes taxes & fees
Nov 18 - Nov 19

Room options

Available filters for rooms
Showing 7 of 7 rooms

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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 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

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 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
Refrigerator
Flat-screen TV
  • 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)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Private bathroom
Shower/tub combination
Hair dryer
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

Similar properties

Lobby
Comfort Inn & Suites Chestertown
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
8.6 out of 10, Excellent, 847 reviews
The price is CNY724
CNY803 total
includes taxes & fees
Nov 18 - Nov 19
Comfort Inn & Suites Chestertown
Mod logo
Sign in to view eligible discounts and perks. More rewards for more adventures!
Sign inSign up, it's free

About the neighborhood

Map
22170 Great Oak Landing Rd, Chestertown, MD, 21620

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 Intl. Airport (BWI) - 101 min drive
  • Baltimore, MD (MTN-Martin State) - 116 min drive

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Tolchester Marina Beach Bar - ‬25 min drive
  • ‪Mangroves Restaurant - ‬5 min walk
  • ‪Clark's Store & Laundrymat - ‬18 min drive
  • ‪Table - ‬17 min walk

About this property

The Lodge at Great Oak Landing

A great stay at The Lodge at Great Oak Landing can include a round of golf at the 9-hole course. You can splash around at the seasonal outdoor pool, visit the restaurant for a bite to eat, or unwind with a drink at one of the 3 bars/lounges.

At a glance

DONE

Hotel size

    • 26 rooms
DONE

Arriving/Leaving

    • Check-in start time: 3:00 PM; Check-in end time: anytime
    • Contactless check-in available
    • Minimum check-in age: 21
    • Check-out time is 11:00 AM
    • Contactless check-out available
DONE

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
DONE

Required at check-in

    • Credit card, debit card, or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 21
DONE

Children

    • No cribs (infant beds)
DONE

Pets

    • Pets not allowed
WIFI

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms (speed: 25+ Mbps)
LOCAL_PARKING

Parking

    • Free uncovered onsite self parking
    • Wheelchair-accessible parking on site
DONE

Other information

    • Smoke-free property

Property amenities

Food and drink

  • 3 bars/lounges
  • Restaurant
  • Coffee/tea in a common area
  • Charcoal grills

Traveling with children

  • Playground
  • Pool gate
  • Fence around the pool

What to do

  • Beach volleyball
  • Private beach access

Services

  • Laundry facilities
  • Beach sun loungers
  • Pool loungers
  • Pool umbrellas

Facilities

  • ATM/banking
  • Picnic area
  • 24-hour fitness center
  • Golf course on site
  • Seasonal outdoor pool
  • Dock
  • Firepit
  • Outdoor entertainment area
  • Outdoor furniture
  • Walkway to water

Accessibility

  • Wheelchair-accessible parking
  • 2 on-site accessible parking spaces
  • Wheelchair-accessible registration desk
  • Wheelchair-accessible registration desk height (inches): 32
  • Wheelchair-accessible restaurant
  • Front entrance ramp
  • Upper floors accessible by stairs only

Room amenities

Be entertained

  • 36-inch flat-screen TV
  • Cable TV channels

Home comfort

  • Climate-controlled air conditioning and heating

Sleep well

  • Bed sheets provided

Freshen up

  • Private bathroom
  • Soap and shampoo
  • Hair dryer
  • Towels
  • Toilet paper

Stay connected

  • Free WiFi (speed of 25+ Mbps)
  • Phone

More

  • Housekeeping on request
  • Connecting/adjoining rooms available

Special features

Dining

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

Fees & policies

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)

Pool, spa, & gym (if applicable)

  • Pool access available from 10:00 AM to 8:00 PM
  • The seasonal pool is open from May 23 to September 18
  • Children under 15 years old are not allowed in the swimming pool or fitness facility without adult supervision

Policies

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.
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.
Noise-free guestrooms cannot be guaranteed.
Only registered guests are allowed in the guestrooms.
This property does not have elevators.
Guests can rest easy knowing there's a smoke detector and outdoor lighting on site.
This property welcomes guests of all sexual orientations and gender identities (LGBTQ+ friendly).
This property accepts credit cards, debit cards and cash.
Credit cards accepted: Visa, Mastercard, American Express, Discover
Cashless transactions are available.

Also known as

The At Great Oak Landing

Frequently asked questions

Does The Lodge at Great Oak Landing offer free cancellation for a full refund?

Yes, The Lodge at Great Oak Landing does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in depending on the property's cancellation policy. Just make sure to check this property's cancellation policy for the exact terms and conditions.

Is there a pool at The Lodge at Great Oak Landing?

Yes, there's a seasonal outdoor pool. Guests have pool access from 10:00 AM to 8:00 PM.

Are pets allowed at The Lodge at Great Oak Landing?

Sorry, pets aren't allowed.

Is parking offered on site at The Lodge at Great Oak Landing?

Yes, there's free self parking.

What are the check-in and check-out times at The Lodge at Great Oak Landing?

Check-in start time: 3:00 PM; Check-in end time: anytime. Check-out time is 11:00 AM. Contactless check-in and check-out are available.

What is there to do at The Lodge at Great Oak Landing and nearby?

Have fun with onsite activities such as volleyball, and practice your swing at the golf course. Enjoy amenities like 3 bars, a seasonal outdoor pool, and a 24-hour fitness center. The Lodge at Great Oak Landing also has a picnic area.

Are there restaurants at or near The Lodge at Great Oak Landing?

Yes, there's an onsite restaurant, Fairlee's.

What's the area around The Lodge at Great Oak Landing like?

The Lodge at Great Oak Landing is located on the waterfront. Popular attractions include Chesapeake Bay, which is 5 minutes away by car.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

The Lodge at Great Oak Landing Reviews

8.0

Very Good

8.6

Cleanliness

7.6

Amenities

8.6

Staff & service

8.2

Eco-friendliness

7.6

Property conditions & facilities

What guests liked

  • The property offers a private beach with comfortable amenities, including chairs and umbrellas. (3 reviews)
AI Sparkle IconFrom real guest reviews summarized by AI.

Reviews

10/10 Exceptional

Nice weekend getaway, friendly staff and good restaurant on premises. Great beach and marina location.
Michelle, 2-night trip

10/10 Exceptional

They've definitely spent a lot of money.
Mark, 1-night trip

10/10 Exceptional

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
KEVIN, 2-night trip

8/10 Very good

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.
Marion, 1-night trip

6/10 Good

Hotel is very outdated, beds are hard as a rock!
Tami, 1-night trip

8/10 Very good

Respite

Generally okay, Clean but property could use some upgrade
Paul, 1-night trip

10/10 Exceptional

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.
Helen, 2-night trip

2/10 Poor

Not clean sheets were damp terrible experience
cecilia, 1-night trip

2/10 Poor

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.
N. Kevin, 3-night trip

4/10 Fair

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.
Ed, 2-night trip

4/10 Fair

WIFI did not work. As such WIFI TV apps (Netflix, Prime, etc) were unavailable.
Steve, 1-night trip

6/10 Good

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
jamie, 1-night trip

2/10 Poor

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.
Todd, 1-night trip

10/10 Exceptional

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.
Ashley, 1-night trip

10/10 Exceptional

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
Francis, 1-night trip

10/10 Exceptional

Getaway

We love this place….awesome pool,and free golf….couldn’t ask for more 😃
Stephen, 3-night trip

8/10 Very good

Great place to get some quiet rest by the water
Philip, 1-night trip

10/10 Exceptional

not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd
Gaines, 1-night trip

6/10 Good

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? 😎
John, 1-night trip

10/10 Exceptional

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!
Christina, 1-night trip

10/10 Exceptional

Wonderful quiet place. Enjoyed our night.
ashley, 1-night trip

6/10 Good

.
Anna, 2-night trip

4/10 Fair

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.
Pam, 2-night trip

8/10 Very good

Over prived

The hotel was functional but a bit high priced for older facility, and small rooms.
Mary Beth, 1-night trip

2/10 Poor

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.
Peter, 1-night trip