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Vacation rentals in Pittsfield

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Top-rated vacation rentals in Pittsfield

Guests agree: these stays are highly rated for location, cleanliness, and more.

Spacious Duplex in Heart of the Berkshires
SUPERHOST
Entire residential home · 4 guests · 2 beds · 1.5 baths
Spacious Duplex in Heart of the BerkshiresEquidistant to MASS MoCA, Tanglewood, Clark Art Institute, Jacob's Pillow, Jiminy Peak, and more, and walking distance to downtown Pittsfield. Spacious, two-floor duplex in the heart of the Berkshires.
Cozy Berkshire cottage with indoor fireplace
Entire cottage · 5 guests · 3 beds · 1.5 baths
Cozy Berkshire cottage with indoor fireplaceRelax at this unique, tranquil getaway. Minutes from all the Berkshires' offer; Tanglewood, Bousquet and Jiminy Peak ski resorts, museums, Colonial and Barrington Theater, Shakespeare and Co, Naumkeag, and many more. Conveniently located on the Pittsfield/Lenox line, close to many restaurants and shopping areas but tucked into the woods with hiking trails on the property. Our kitchen has all your cooking essentials. We have smart TV's and WIFI to relax with after your Berkshire adventures.
Lakefront Cottage Jiminy Ice Fishing Berkshire
SUPERHOST
Entire cottage · 6 guests · 6 beds · 1 bath
Lakefront Cottage Jiminy Ice Fishing BerkshireDive into the beauty of the Berkshires with this lakefront vacation rental cottage. When you're not enjoying the lake, get out and explore the best of the Berkshires including Mt. Greylock and Tanglewood! In the winter months, enjoy a weekend of ice fishing or go skiing at nearby Jiminy Peak or newly renovated Bousquet Mountain!

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Other great vacation rentals in Pittsfield

SUPERHOST
  1. Entire rental unit
  2. Pittsfield
Berkshire Luxury Apartment Home with Workstation
$200 per night
SUPERHOST
  1. Entire rental unit
  2. Pittsfield
The sweet place in the beautiful Berkshires!
$76 per night
  1. Entire rental unit
  2. Lanesborough
Bright and cozy getaway on a historic farm
$131 per night
  1. Entire residential home
  2. Pittsfield
Pontoosuc Place - Cheerful Home in the Berkshires
$165 per night
SUPERHOST
  1. Entire rental unit
  2. Pittsfield
Lovely 1-Bedroom Apartment Rental - Skiing Nearby!
$106 per night
SUPERHOST
  1. Entire residential home
  2. Pittsfield
Hidden Oasis in the Berkshire Mountains
$483 per night
  1. Entire residential home
  2. Cheshire
Berkshire County modern home + pool
$379 per night
SUPERHOST
  1. Private room
  2. Pittsfield
Large guest suite w/private bath in the Berkshires
$77 per night
SUPERHOST
  1. Entire residential home
  2. Stephentown
Dog Friendly Studio
$150 per night
  1. Entire rental unit
  2. Pittsfield
HawksNest: quiet 2BR apt, heart of the Berkshires
$86 per night
SUPERHOST
  1. Entire residential home
  2. Pittsfield
Honeysuckle Rose Cottage
$116 per night
SUPERHOST
  1. Entire residential home
  2. Dalton
The Yellow House
$78 per night