Beginning of main content

location Chestertown is highly rated for Lakes and Coffee by 29 people

Search 590,000 properties worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Check prices on hotels in Chestertown

Tonight Tonight Feb 20 - Feb 21
This weekend This weekend Feb 23 - Feb 25
Next weekend Next weekend Mar 2 - Mar 4

Top 10 Hotels in Chestertown

See all 5 Hotels in Chestertown
Friends Lake Inn

Friends Lake Inn

963 Friends Lake Rd, Chestertown
4.5 out of 5.0
Last booking: 4 days ago
6 others viewing this property now

Located in the mountains, this ski-in/ski-out hotel in Chestertown is within 12 mi (20 km) of Pack Demonstration Forest and Natural Stone Bridge and Caves and ...

$189

$189
The Fern Lodge

The Fern Lodge

46 Fiddlehead Bay Rd, Chestertown
3.5 out of 5.0

Situated on a lake, this bed & breakfast is 8.1 mi (13 km) from Pack Demonstration Forest and within 16 mi (25 km) of Natural Stone Bridge and Caves and Hickory ...

$395

$395
Loon Lake Retreat With Private Dock

Loon Lake Retreat With Private Dock

112 Marina Rd, Chestertown

Situated in a rural location, this vacation home is in the same area as Natural Stone Bridge and Caves. Regional attractions also include Tannery Pond Community ...

Get Rates

Get Rates
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown
2.5 out of 5.0
1 others viewing this property now

Situated near the beach, this motel is within 12 mi (20 km) of Pack Demonstration Forest, Natural Stone Bridge and Caves, and Avalanche Lake. Tannery Pond Community ...

Get Rates

Get Rates
Gore Mountain Lodge

Gore Mountain Lodge

881 Peaceful Valley Roads, North Creek
Last booking: 2 days ago
2 others viewing this property now

Situated on a river, this motel is within 2 mi (3 km) of Tannery Pond Community Center, North Creek Depot Museum, and Gore Mountain Ski Resort. Straightbrook ...

$159

$159
Sunset Mountain Lodge

Sunset Mountain Lodge

7296 Route 8, Brant Lake
3.5 out of 5.0

Situated on a lake, this cottage is within 16 mi (25 km) of Avalanche Lake, Natural Stone Bridge and Caves, and Up Yonda Farm Environmental Education Center. ...

Get Rates

Get Rates
Sale Fall Foliage! Relax and Explore W/walking Trail, Fields, & Moss Beds!

Sale Fall Foliage! Relax and Explore W/walking Trail, Fields, & Moss Beds!

State Route 8, Wevertown

Situated in a rural location, this vacation home is in the same area as Gore Mountain Ski Resort, North Creek Ski Bowl Town Park, and Tannery Pond Community ...

Get Rates

Get Rates
SKI Gore Mountain! Beautiful NEW Home Sleeps 10 AND Close TO Skiing AND Village

SKI Gore Mountain! Beautiful NEW Home Sleeps 10 AND Close TO Skiing AND Village

721 Peaceful Valley Rd, North Creek

Situated in North Creek, this property is close to Gore Mountain Ski Resort, North Creek Ski Bowl Town Park, and Tannery Pond Community Center. Local attractions ...

Get Rates

Get Rates
Adirondack Waterfront Log Cabin-with Wifi

Adirondack Waterfront Log Cabin-with Wifi

1288 Schroon River Rd, Warrensburg

Situated in Warrensburg, this property is in the same area as The Sembrich, Pack Demonstration Forest, and Up Yonda Farm Environmental Education Center. Area ...

Get Rates

Get Rates
Alynn's Butterfly Inn Bed & Breakfast

Alynn's Butterfly Inn Bed & Breakfast

69 Route 28, Warrensburg
3.5 out of 5.0

Situated in Warrensburg, this romantic bed & breakfast is 2.1 mi (3.4 km) from Pack Demonstration Forest and within 9 mi (15 km) of Hickory Ski Center and Black ...

Get Rates

Get Rates
Map

Recent Reviews in Chestertown