Pittsfield Chalets

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Chalets in Pittsfield

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.

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

Cropseyville NY

$1,324 nightly

$1,470 total

Apr 1 - Apr 2

Total with taxes and fees

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.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut

Monterey MA

Located in Monterey, this chalet is on a lake, within a 15-minute drive of Bidwell House Museum and Ashintully Gardens.

Joia Verde: Mtn Chalet -120 Acres -Adventure Ski Hike

Charlemont MA

When you stay at this chalet in Charlemont, you'll be in the mountains, within a 5-minute drive of Deerfield River and Rowe Town Forest.

Majestic Lake Front Chalet

Valatie NY

Located in Valatie, this chalet is a 5-minute drive from Kinderhook Lake and 5 minutes from Valatie Family Care.

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.

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.