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The Lodge at Great Oak Landing

3.5 star property
3.5-star beach lodge with 3 bars/lounges

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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
Private beach nearby, sun loungers, beach volleyball
Point of interest

Reviews

8.0 out of 10
Very good

Popular amenities

  • Bar
  • Pool
  • Gym
  • Laundry
  • Air conditioning
  • Parking included

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

Walk to the beach.At this Chestertown lodge, you'll be within 9 miles (15 km) of Washington College and 12 miles (20 km) of Garfield Center for the Arts at the Prince Theater. The Mainstay is within 16 miles (25 km) and Church Hill Theatre is within 20 miles (32 km).
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
  • ‪Unruh's Carryout - ‬21 min drive
  • ‪Chestertown Cooking Company - ‬29 min drive
  • ‪Harbor House Restaurant - ‬12 min drive

About this property

The Lodge at Great Oak Landing

3.5-star beach lodge with 3 bars/lounges
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.

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.

  • 29 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 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.

Similar properties

Lobby

Comfort Inn & Suites Chestertown

  • Pool
  • Breakfast included
  • Pet friendly
  • Parking included
4.3 out of 5, Excellent, 812 reviews
$110 nightly
The price is $122
Sep 14 - Sep 15
Total with taxes and fees
Comfort Inn & Suites Chestertown

Property amenities

Family friendly

  • Fenced pool
  • Laundry facilities
  • Playground
  • Pool gate
  • Seasonal outdoor pool

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

Things to do

  • 24-hour gym
  • 9-hole golf course
  • Beach volleyball
  • Playground
  • Seasonal outdoor pool

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

Room amenities

Entertainment

  • 36-inch flat-screen TV with cable channels

Bedroom

  • Bedsheets provided

Bathroom

  • Hair dryer
  • Private bathroom
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

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)
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

  • No pets 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
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, 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. 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 each accommodation. Cashless payment methods are available for all transactions.

We should mention

  • The seasonal pool will open May 23 and close September 18.
  • 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

How close is The Lodge at Great Oak Landing to the airport?

The Lodge at Great Oak Landing is 88.1 mi (116-min drive) away from the Baltimore, MD (MTN-Martin State) airport, the closest popular airport to the property.

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

As of Sep 8, 2025, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on Sep 16, 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.

Does The Lodge at Great Oak Landing have an airport shuttle?

Airport shuttle services are not available at The Lodge at Great Oak Landing.

How close is The Lodge at Great Oak Landing to the beach?

This lodge is 14.7 mi (31-min drive) from Betterton Beach and 14.7 mi (35-min drive) from Main Beach. Don't forget your sunscreen!

Does The Lodge at Great Oak Landing offer free breakfast?

The Lodge at Great Oak Landing does not offer free breakfast.

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

No, there is no casino at this lodge.

What time is check-in at The Lodge at Great Oak Landing?

Check-in start time: 3:00 PM; Check-in end time: anytime.

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

This lodge offers free self parking.

Does The Lodge at Great Oak Landing have a pool?

The Lodge at Great Oak Landing features a seasonal outdoor pool. Guests can enjoy pool access from 10:00 AM to 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.

Does The Lodge at Great Oak Landing have a restaurant?

Yes, there is a restaurant on site. The dining venue(s) are closed on Christmas Eve, Christmas Day, New Year's Eve, and New Year's Day.

Does The Lodge at Great Oak Landing have a spa?

There are no spa services available at this lodge.

How close is The Lodge at Great Oak Landing to downtown Chestertown?

The Lodge at Great Oak Landing is 0.2 mi away from Great Oak Landing.

The Lodge at Great Oak Landing Reviews

Reviews

8.0

Very Good

Rating 10 - Excellent. 35 out of 68 reviews
Rating 8 - Good. 13 out of 68 reviews
Rating 6 - Okay. 9 out of 68 reviews
Rating 4 - Poor. 4 out of 68 reviews
Rating 2 - Terrible. 7 out of 68 reviews

8.6/10

Cleanliness

8.8/10

Staff & service

7.6/10

Amenities

7.8/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

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

10/10 Excellent

Sharon

Liked: Cleanliness, staff & service, property conditions & facilities
My only complaint is hard pillows. Loved the surroundings and wish we had more time there.
Stayed 2 nights in Sep 2024

6/10 Okay

George

Traveled with family
Liked: Amenities
Bathroom sink was clogged. No closet for clothes…just a small rack with 1 hanger WiFi poor No elevator to second floor Pool water temperature very cold No breakfast availability, either at hotel or within walking distance elsewhere. Location was excellent, next to boat docks and Tiki Bar. Dinner at hotel restaurant delicious and reasonably priced. Friendly staff. Room was clean. All in all, the marina is an excellent destination, but the hotel facility itself could be better.
Stayed 1 night in Sep 2024

6/10 Okay

ANNE

Liked: Staff & service
Disliked: Cleanliness, amenities, property conditions & facilities
rugs are so stained and worn that they appear to not be clean even if they've been shampoo'd. Woodwork is grimy with dirt no dressers available although there was plenty of room for at least 2 there is no counter space in the bathroom The desk staff was very responsive and pleasant, and the restaurant, the view, and the marina are all really excellent
Stayed 2 nights in Sep 2024