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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

Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.
Relax by the pool surrounded by lounge chairs and a deck.
Stately brick building with a central entrance and two tall chimneys, set amidst well-maintained lawns and mature trees.
Enjoy serene lakeside views and relax on the sandy shore with picnic tables and lounge chairs.
Stroll through the serene garden, surrounded by a tranquil fountain and beautifully landscaped greenery.

Popular amenities

  • Bar
  • Pool
  • Gym
  • Laundry
  • Air conditioning
  • Parking included
The current price is AU$220
includes taxes & fees
3 Aug - 4 Aug

Explore the area

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

Standard Room, 1 King Bed

Highlights

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

View all photos for Room, 1 King Bed

Room, 1 King Bed

Room, 1 King Bed

8.0 out of 10
Very good
(1 review)

Highlights

Air conditioning
Connecting rooms available
Mini-fridge
Flat-screen TV
Separate bedroom
Shower/bath combination
Hairdryer
Private bathroom
  • 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
Shower/bath combination
Hairdryer
Private bathroom
  • Water view
  • Sleeps 3
  • 1 King Bed and 1 Single Sofa Bed

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

Room, 2 Queen Beds, Marina View

Room, 2 Queen Beds, Marina View

9.0 out of 10
Wonderful
(2 reviews)

Highlights

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

Highlights

Furnished balcony
Separate sitting area
Individually furnished
Individually decorated
Air conditioning
Connecting rooms available
Fridge
Flat-screen TV
  • Marina view
  • Sleeps 5
  • 1 King Bed, 1 Single Sofa Bed and 1 Double Sofa 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 - 23 min drive - 17.3 km
  • River Arts Chestertown - 24 min drive - 18.7 km
  • The Mainstay - 33 min drive - 23.7 km
  • Rock Hall Harbor - 34 min drive - 24.4 km
  • Eastern Neck National Wildlife Refuge - 44 min drive - 34.9 km

Getting around

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

Restaurants

  • ‪Jellyfish Joel's - ‬5 min walk
  • ‪Mears Great - ‬5 min walk
  • ‪Tolchester Restaurant - ‬25 min drive
  • ‪JR's Watermark Grille - ‬5 min walk
  • ‪Inn At Worton Creek - ‬12 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.

  • 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 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.

Languages

English

Similar properties

Welcome to our reception area, where friendly staff are available to assist with your stay.

Comfort Inn & Suites Chestertown

  • Pool
  • Breakfast included
  • Pet-friendly
  • Parking included
4.3 out of 5, Excellent, 787 reviews
The price is AU$193
includes taxes & fees
3 Aug - 4 Aug
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
  • 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 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 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 31 July 2025, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on 3 Aug 2025 start from AU$219.85, 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

8.0

Very good

Rating 10 - Excellent. 28 out of 57 reviews
Rating 8 - Good. 13 out of 57 reviews
Rating 6 - Okay. 7 out of 57 reviews
Rating 4 - Poor. 4 out of 57 reviews
Rating 2 - Terrible. 5 out of 57 reviews

8.6/10

Cleanliness

8.8/10

Staff & service

7.4/10

Amenities

7.8/10

Property conditions & facilities

8.2/10

Eco-friendliness

Reviews

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

10/10 Excellent

KRISTIAN

Stayed 2 nights in Oct 2024

2/10 Terrible

N. Kevin

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

2/10 Terrible

Peter

Travelled 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

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

8/10 Good

Marion

Travelled 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

Travelled with family
Disliked: Amenities
Not clean sheets were damp terrible experience
Stayed 1 night in Sep 2024

8/10 Good

Verified traveller

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

Travelled 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

Travelled 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

8/10 Good

Julie, Schaumburg

Liked: Cleanliness, staff & service
This property is just fine for a 1-2 night stay. The rooms aren't equipped with amenities needed to make a longer stay comfortable.
Stayed 1 night in Sep 2024

8/10 Good

Thomas

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Stayed 2 nights in Jul 2024