Best price vacation rentals in Pittsfield, MA 01201, USA • 150 Listings
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Pittsfield, MA 01201, 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 (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 (123)
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
Up to 9 guests
Airbnb$446
Vrbo$488
Average Nightly Rate
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5.0 (60)
Historical Downtown 1bedroom
Up to 2 guests
Airbnb$238
Vrbo$238
Average Nightly Rate
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5.0 (11)
BERKSHIRES-4BR2BA TANGLEWOOD, SUMMER/Avail June and Aug 1-Labor Day
Up to 8 guests
Airbnb$116
Vrbo$117
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 (31)
Tranquil Berkshires Retreat
Up to 11 guests
Airbnb$857
Vrbo$936
Average Nightly Rate
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5.0 (6)
Magic Richmond property with stunning views- 3BR Farmhouse and 2BR Guesthouse.
Up to 12 guests
Airbnb$402
Vrbo$406
Average Nightly Rate
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5.0 (34)
Beautiful Home in AMAZING Berkshire Location
Up to 10 guests
Airbnb$482
Vrbo$482
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 (76)
CABIN FEVER IN STOCKBRIDGE
Up to 6 guests
Airbnb$260
Vrbo$564
Average Nightly Rate
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5.0 (7)
Cozy cottage minutes away from Tanglewood and Stockbridge center
Up to 4 guests
Airbnb$170
Vrbo$170
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 (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 (2)
Fox Hollow Lakeside Condo, Minutes to Tanglewood
Up to 12 guests
Airbnb$299
Vrbo$299
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 (25)
Stockbridge Bowl Lake Community
Up to 7 guests
Airbnb$366
Vrbo$385
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 (180)
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
Up to 6 guests
Airbnb$353
Vrbo$495
Average Nightly Rate
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5.0 (175)
Heart of Lenox Walk to Town Cozy Cottage!
Up to 4 guests
Airbnb$283
Vrbo$283
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 (101)
Beauty in the Berkshires ..
Up to 16 guests
Airbnb$1,500
Vrbo$1,500
Average Nightly Rate
  1. United States
  2. Massachusetts
  3. Pittsfield Vacation Rental Price Comparison

Compare Airbnb vs. Booking.com vs. Vrbo prices for vacation rentals in Pittsfield, MA 01201, USA

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