Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chestertown Flight + Hotel packages

Chestertown Hotels

See all 157 Hotels in Chestertown
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown
2.0 out of 5.0
5.0 out of 5 (1 reviews)

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

$125

$125
Friends Lake Inn

Friends Lake Inn

963 Friends Lake Rd, Chestertown
4.0 out of 5.0
5.0 out of 5 (1 reviews)

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 romantic vacation home is within 12 mi (20 km) of Natural Stone Bridge and Caves, Avalanche Lake, and Tannery Pond Community ...

Lily Pad South @ Loon Lake, in the Adirondacks Near Gore Mountain

Lily Pad South @ Loon Lake, in the Adirondacks Near Gore Mountain

7131 State Route 9, Chestertown

Located in the heart of Chestertown, this apartment is within 12 mi (20 km) of Natural Stone Bridge and Caves, Avalanche Lake, and Moxham Mountain. Tannery Pond ...

The Lily Pad North at Loon Lake, in the Adirondacks Near Gore Mountain

The Lily Pad North at Loon Lake, in the Adirondacks Near Gore Mountain

7131 State Route 9, Chestertown

Located in the heart of Chestertown, this historic apartment is within 12 mi (20 km) of Natural Stone Bridge and Caves, Avalanche Lake, and Moxham Mountain. ...

The Lily Pad @ Loon Lake w/ Dock Near Lake George & Gore Mountain

The Lily Pad @ Loon Lake w/ Dock Near Lake George & Gore Mountain

7131 State Route 9, Chestertown

Located in the heart of Chestertown, this historic vacation home is within 12 mi (20 km) of Natural Stone Bridge and Caves, Avalanche Lake, and Moxham Mountain. ...

Eagles Nest at Loon Lake With Dock Near Lake George & Gore Mountain

Eagles Nest at Loon Lake With Dock Near Lake George & Gore Mountain

7129 State Route 9, Chestertown

Located in the heart of Chestertown, this romantic vacation home is within 12 mi (20 km) of Natural Stone Bridge and Caves, Avalanche Lake, and Moxham Mountain. ...

Wingate by Wyndham Lake George

Wingate by Wyndham Lake George

4054 State Route 9L, Lake George
2.5 out of 5.0
4.2 out of 5 (87 reviews)

Situated in Lake George, this hotel is within a 15-minute walk of Water Slide World and Fort William Henry. Lake George Beach is 0.9 mi (1.4 km) away.

$76

$76
Lake George Diamond Cove

Lake George Diamond Cove

3648 Lake Shore Dr, Lake George
3.0 out of 5.0

This Lake George hotel is on the beach, 1.6 mi (2.6 km) from Hearthstone Point Campground, and within 6 mi (10 km) of Lake George Beach and Million Dollar Beach. ...

Map

* Prices reflect the lowest "base rate" found over the next 30 days. Rates are subject to change and may not include taxes and fees, hotel service charges, extra person charges, or incidentals, such as room service. All rates are displayed in USD unless otherwise noted. Converted rates are provided for your convenience. They are based on today's exchange rate, but the hotel will charge you in the local currency.