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Compare 43 Resorts in Pittsfield with updated reviews, rates, and availability.

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
9.8 out of 10, Exceptional, (38)

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
10.0 out of 10, Exceptional, (3)

Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
9.6 out of 10, Exceptional, (4)

Lg 1 Bd - Vacation Village in the Berkshires
Lg 1 Bd - Vacation Village in the Berkshires
10.0 out of 10, Exceptional, (2)

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

COZY CABIN IN BERKSHIRES RESORT
COZY CABIN IN BERKSHIRES RESORT
9.6 out of 10, Exceptional, (16)

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.6 out of 10, Excellent, (10)

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
9.6 out of 10, Exceptional, (4)
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

Hancock Village Inn at Jiminy Peak
Hancock Village Inn at Jiminy Peak
9.8 out of 10, Exceptional, (10)
The price is AED 2,016
AED 3,810 total
includes taxes & fees
5 May - 6 May

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, (140)

Dancing Horse Lodge
Dancing Horse Lodge
9.6 out of 10, Exceptional, (41)
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

Berkshire Mountain Lodge
5/5 Excellent
"Love it and enjoy it. Safe, quiet, well-kept, nice property and most of all very friendly staff. "
A verified traveler stayed at Berkshire Mountain Lodge
Posted 23 hours ago
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