Best price vacation rentals in Cheshire, MA, USA • 150 Listings
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Cheshire, MA, USA Vacation Rentals | 

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5.0 (35)
Free standing private Ski in/Ski out 4 BR Home on Jiminy Peak
Up to 12 guests
Airbnb$943
Vrbo$943
Average Nightly Rate
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5.0 (35)
11 acre mid-century estate, newly renovated
Up to 8 guests
Airbnb$849
Vrbo$849
Average Nightly Rate
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5.0 (27)
Tentrr Signature Site - Round Mountain Camp
Up to 6 guests
Airbnb$97
Vrbo$99
Average Nightly Rate
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5.0 (38)
Berkshires Jiminy Peak Mountainside Condo
Up to 6 guests
Vrbo$399
Airbnb$417
Average Nightly Rate
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5.0 (49)
Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
Up to 6 guests
Vrbo$185
Airbnb$199
Average Nightly Rate
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5.0 (34)
Hidden Oasis in the Berkshire Mountains
Up to 10 guests
Airbnb$564
Vrbo$564
Average Nightly Rate
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5.0 (18)
Wyndham Bentley Brook Ski-In Ski-Out Resort
Up to 8 guests
Vrbo$389
Airbnb$500
Average Nightly Rate

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5.0 (1)
NEW! Lakeside Berkshires Home Near Hiking & Skiing
Up to 8 guests
Airbnb$307
Vrbo$1,026
Average Nightly Rate
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5.0 (6)
NEW! Peaceful Family Home w/ Fire Pit & Large Yard
Up to 6 guests
Airbnb$266
Vrbo$987
Average Nightly Rate

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5.0 (14)
Walk to town! Hiking & biking galore! Fireplace, patio, mtn views! Kid friendly!
Up to 8 guests
Vrbo$172
Airbnb$261
Average Nightly Rate
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5.0 (4)
Mountainside: Large 3-level Jiminy Peak Home
Up to 8 guests
Airbnb$335
Vrbo$339
Average Nightly Rate
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5.0 (124)
The Bear’s Den @ America's Switzerland
Up to 2 guests
Airbnb$182
Vrbo$205
Average Nightly Rate
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5.0 (23)
Wyndham Bentley Brook - Jiminy Peak ski in/out
Up to 8 guests
Airbnb$350
Vrbo$429
Average Nightly Rate
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5.0 (16)
Lakeside Home With Pool-Completely Renovated
Up to 16 guests
Airbnb$575
Vrbo$600
Average Nightly Rate
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5.0 (85)
Spacious Victorian in N. Adams-walk to Mass MoCA
Up to 9 guests
Airbnb$338
Vrbo$338
Average Nightly Rate
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5.0 (23)
Berkshires Retreat at Family Friendly Hygge House
Up to 6 guests
Airbnb$321
Vrbo$388
Average Nightly Rate
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5.0 (129)
A roomy remodeled retreat close to MassMoCA
Up to 8 guests
Airbnb$227
Vrbo$228
Average Nightly Rate
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5.0 (112)
Berkshire Pontoosuc Lake Beauty Too-Brand new construction on the lake
Up to 14 guests
Airbnb$464
Vrbo$464
Average Nightly Rate
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5.0 (100)
Berkshire Cottage on Ashmere Lake
Up to 6 guests
Airbnb$115
Vrbo$129
Average Nightly Rate
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5.0 (99)
Charming Downtown Williamstown Cottage - 5 min walk to Campus
Up to 7 guests
Vrbo$213
Airbnb$227
Average Nightly Rate
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5.0 (139)
Brooksong, the perfect Berkshires getaway
Up to 10 guests
Vrbo$400
Airbnb$415
Average Nightly Rate
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5.0 (274)
Swiss Chalet Style Timber frame Home In Berkshires With All Modern Conveniences
Up to 6 guests
Airbnb$210
Vrbo$210
Average Nightly Rate
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5.0 (95)
Elegant house nestled in the scenic hills of Northern Berkshire County.
Up to 14 guests
Vrbo$460
Airbnb$475
Average Nightly Rate
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5.0 (157)
Dancing Horse Lodge
Up to 6 guests
Airbnb$130
Vrbo$130
Average Nightly Rate
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5.0 (30)
SKI-IN, SKI-OUT! UNBEATABLE LOCATION for ALL SEASONS!Closest Condo Unit to Lifts
Up to 10 guests
Airbnb$448
Vrbo$488
Average Nightly Rate
  1. United States
  2. Massachusetts
  3. Cheshire Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Cheshire, MA, USA

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