The Lodge at Great Oak Landing

Lodge with private beach, seasonal outdoor pool

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Where to?

Dates

October 2025

November 2025

Private beach nearby, sun loungers, beach volleyball

Room, 1 King Bed with Sofa bed, Marina View | 1 bedroom, free WiFi, bed sheets

The Lodge at Great Oak Landing offers a waterfront stay with a private beach and sun loungers. Enjoy golf, summer drinks at the poolside bar, or evening firepit gatherings. Free in-room WiFi, express check-out, and charcoal grills for outdoor cooking are provided.

Good

Popular amenities

Bar
Gym
Pool
Laundry
Air conditioning
Free WiFi

NT$4,595 total

includes taxes & fees

Oct 7 - Oct 8

Room options

Check availability for these dates

Tonight

Oct 6 - Oct 7

Tomorrow

Oct 7 - Oct 8

All rooms

1 bed

2 beds

3+ beds

Showing 7 of 7 rooms

Room, 2 Queen Beds, Marina View

Excellent

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Water view
Sleeps 4
2 Queen Beds

Standard Room, 1 King Bed

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Sleeps 2
1 King Bed

Room, 1 King Bed with Sofa bed, Marina View

Exceptional

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Water view
Sleeps 3
1 King Bed and 1 Twin Sofa Bed

Standard Room, 2 Double Beds

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Sleeps 4
2 Double Beds

Room, 1 Queen Bed, Accessible

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Sleeps 2
1 Queen Bed

Suite

Very good

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

Room, 1 King Bed

Wonderful

Highlights

Air conditioning

Connecting rooms available

Mini-fridge

Flat-screen TV

Separate bedroom

Hair dryer

Shower/tub combination

Private bathroom

1 bedroom
Sleeps 2
1 King Bed

About the neighborhood

Located in Chestertown, The Lodge at Great Oak Landing is in a rural area and on the waterfront. Garfield Center for the Arts at the Prince Theater and The Mainstay are cultural highlights, and travelers looking to shop may want to visit Queenstown Premium Outlets. Washington College and Church Hill Theatre are two other places to visit that come recommended.

Visit our Chestertown travel guide

View more Lodges in Chestertown

22170 Great Oak Landing Rd, Chestertown, MD, 21620

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 Intl. Airport (BWI) - 101 min drive

Restaurants

‪Jellyfish Joel's - ‬5 min walk
‪Tolchester Marina Beach Bar - ‬25 min drive
‪Mangroves Restaurant - ‬5 min walk
‪Harbor House - ‬13 min drive
‪Chestertown Cooking Company - ‬29 min drive

About this property

The Lodge at Great Oak Landing

Lodge on the waterfront

Take advantage of a golf course, a firepit, and a playground at The Lodge at Great Oak Landing. This lodge is a great place to bask in the sun with a nearby private beach, sun loungers, and beach volleyball. Be sure to enjoy a meal at Fairlee's, the on-site restaurant. Free in-room WiFi, with speed of 25+ Mbps, is available to all guests, along with laundry facilities and an outdoor entertainment area.

You'll also enjoy perks such as:

A seasonal outdoor pool along with sun loungers and pool umbrellas
Free self parking
Outdoor furniture, a gift shop, and a dock
Charcoal grills, smoke-free premises, and ATM/banking services

Room features

All guestrooms at The Lodge at Great Oak Landing feature comforts such as air conditioning, in addition to amenities like free WiFi.

Extra amenities include:

Bathrooms with hair dryers and shampoo
36-inch flat-screen TVs with cable channels
Heating, housekeeping, and phones

Similar properties

Pool
Breakfast included
Pet friendly
Parking included

NT$3,856 total

includes taxes & fees

Nov 3 - Nov 4

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

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

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) and Friday - Saturday (8:30 AM - 6:00 PM)

Guests will receive an email within 24 hours before arrival with check-in instructions and an access code; 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

Frequently asked questions

Does The Lodge at Great Oak Landing have a pool?

Yes, this property has a seasonal outdoor pool. Pool access is from 10:00 AM–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.

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

As of 2025/10/6, prices found for a 1-night stay for 2 adults at The Lodge at Great Oak Landing on 2025/10/7 start from NT$4,019, 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.

Is The Lodge at Great Oak Landing pet-friendly?

No, pets are not allowed at this property.

How much is parking at The Lodge at Great Oak Landing?

Self parking is free at this property.

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

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

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

Check-out is at 11:00 AM.

Where is The Lodge at Great Oak Landing located?

Offering direct access to the beach, this Chestertown lodge is 8.8 mi (14.2 km) from Washington College and within 16 mi (25 km) of Garfield Center for the Arts at the Prince Theater and The Mainstay. Church Hill Theatre and Eastern Neck National Wildlife Refuge are also within 20 mi (32 km).

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The Lodge at Great Oak Landing

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Photo gallery for The Lodge at Great Oak Landing

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Popular amenities

Room options

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

Room, 2 Queen Beds, Marina View

Highlights

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed

Highlights

View all photos for Room, 1 King Bed with Sofa bed, Marina View

Room, 1 King Bed with Sofa bed, Marina View

Highlights

View all photos for Standard Room, 2 Double Beds

Standard Room, 2 Double Beds

Highlights

View all photos for Room, 1 Queen Bed, Accessible

Room, 1 Queen Bed, Accessible

Highlights

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Suite

Highlights

View all photos for Room, 1 King Bed

Room, 1 King Bed

Highlights

About the neighborhood

What's nearby

Getting around

Restaurants

About this property

The Lodge at Great Oak Landing

Similar properties

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Property amenities

Internet

Parking and transportation

Food and drink

Restaurants on site

Things to do

Family friendly

Conveniences

Guest services

Outdoors

Accessibility

More

Room amenities

Bedroom

Bathroom

Entertainment

More

Policies

Check-in

Check-out

Special check-in instructions

Renovations and closures

Access methods

Pets

Children and extra beds

Property payment types

Important information

You need to know

We should mention

Property is also known as

Frequently asked questions

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