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Compare 33 Resorts in Cummington with updated reviews, rates, and availability.

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

Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Jiminy Premier Ski-In/Ski-Out Resort Bentley B
10.0 out of 10, Exceptional, (2)

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)

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
10.0 out of 10, Exceptional, (1)

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

SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
9.6 out of 10, Exceptional, (15)

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.8 out of 10, Excellent, (9)

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)
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 Cummington

The Clearing - Quiet - Close To Nature
The Clearing - Quiet - Close To Nature
10.0 out of 10, Exceptional, (187)

Vacation Village in the Berkshires
Vacation Village in the Berkshires
8.6 out of 10, Excellent, (1791)
The price is AED 437
AED 520 total
includes taxes & fees
24 Mar - 25 Mar

The Ponds at Foxhollow
The Ponds at Foxhollow
8.6 out of 10, Excellent, (120)
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 Cummington hotels
Recent reviews of Cummington hotels

Life House Berkshires
5/5 Excellent
"We thought the pictures were too good to be true for the price.
We were pleasantly surprised.
Life House Berkshires was very nice.
Staff was wonderful and friendly. The room was clean, nicely decorated, bathroom was big.
We would definitely stay again."
A verified traveler stayed at Life House Berkshires
Posted 17 hours ago
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