Cheshire Chalets

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Chalets in Cheshire

Little Longbow Lakefront Chalet

Becket MA

A stay at this chalet places you in the heart of Becket, within a 5-minute drive of Pyramid Lake and Jacob's Pillow.

Kitchen

Washer

28 Acre Private Luxury Chalet-Hot Tub-Heated Pool-Game Rooms-16 ppl-pet friendly

Cropseyville NY

Located in Cropseyville, this chalet is in a rural location, within a 15-minute drive of Grafton Lakes State Park and Pineridge Cross Country Ski Center.

Sunny Chalet Nestled in the Woods of Ashfield

Ashfield MA

Located in Ashfield, this chalet is on the waterfront, within a 5-minute drive of Steady Lane/Hill Cemetery and Land of Providence.

SRC-Hudson Valley/Berkshires Cultural Corridor

Canaan NY

Located in Canaan, this chalet is in the mountains, a 5-minute drive from Queechy Lake and 8 minutes from Furnace Brook Winery at Hilltop Orchards.

Secluded Mountain Chalet

Whitingham VT

Located in Whitingham, this chalet is in the mountains, within a 10-minute drive of Harriman Reservoir and Jacksonville Pond.

Cozy 3-bedroom chalet with mountain views

Canaan NY

Located in Canaan, this chalet is a 4-minute drive from Queechy Lake and 5 minutes from Furnace Brook Winery at Hilltop Orchards.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.