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Compare 5 Chalets in Pittsfield with updated reviews, rates, and availability.

Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
9.8 out of 10, Exceptional, (23)

Little Longbow Lakefront Chalet
Little Longbow Lakefront Chalet
9.2 out of 10, Wonderful, (10)

SRC-Hudson Valley/Berkshires Cultural Corridor
SRC-Hudson Valley/Berkshires Cultural Corridor

Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
Private Luxury Chalet-Hot Tub-Heated Pool-Firepit-Game Rooms-Fits 16 people
10.0 out of 10, Exceptional, (1)

Majestic Lake Front Chalet
Majestic Lake Front Chalet
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.
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Other property types in Pittsfield

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
9.8 out of 10, Exceptional, (139)

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is SAR 2,243
SAR 3,981 total
includes taxes & fees
5 Mar - 6 Mar

Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
10.0 out of 10, Exceptional, (56)
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.
Recent reviews of Pittsfield hotels
Recent reviews of Pittsfield hotels

The Yankee, Trademark Collection by Wyndham
5/5 Excellent
"This was a very nice little getaway from everyday life. The room was nice and roomy and we loved the fireplace. "
A verified traveler stayed at The Yankee, Trademark Collection by Wyndham
Posted 19 hours ago
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