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Vacation rentals in West Stockbridge

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Top-rated vacation rentals in West Stockbridge

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

Cottage with indoor fireplace and outdoor hot tub
SUPERHOST
Entire cottage · 2 guests · 1 bed · 2 baths
Cottage with indoor fireplace and outdoor hot tubEnchanting cottage and lodge building with fireplaces in a quaint, quiet, neighborhood with separate wood lodge for lounging and eating. Private Jacuzzi, outdoor shower, outdoor fireplace and gardens. Nature trails a short walk nearby. Perfect for a romantic get-away. Open retro style kitchen with new vintage style gas stove and living area with a bathroom. Upstairs bedroom has balcony to view stars with large bathroom, soaking tub and chair that messages for the perfect relaxing vacation
Must Love trains and a Fire Place!
SUPERHOST
Entire residential home · 4 guests · 2 beds · 1.5 baths
Must Love trains and a Fire Place!This house is very spacious with open concept vaulted living room open to the kitchen and formal dinning room. Full size washer dryer on the first floor with half bath. Second floor has 2 bedrooms one with a Queen bed and one with a King bed with TV and desk area. The full bathroom with shower is on the 2nd floor. Bonus living room on the first floor. The train comes by twice a day but not on Saturday. Timing is usually once between 10am and 2pm and once between 4pm and 7pm. Garage can be used.
Elegant Year-Round Lakeside Retreat
SUPERHOST
Entire residential home · 8 guests · 6 beds · 3 baths
Elegant Year-Round Lakeside RetreatThe Haven, an elegant cottage surrounded by woods, located on a pristine lake with private dock. 4 bedrooms, 3 baths. This year-round vacation cottage with hot tub provides an experience in the Berkshires you won’t forget! Leaf-peep in fall, ski in winter, hike in spring, kayak & swim in summer, or browse the boutique shops in quaint towns like Great Barrington, Lenox and Stockbridge. Dogs ok.

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Other great vacation rentals in West Stockbridge

  1. Entire residential home
  2. West Stockbridge
[NEW] Sunny 4BR, mins to Skiing, Tanglewood & Bowl
$525 per night
SUPERHOST
  1. Entire residential home
  2. West Stockbridge
Berkshires Forest Retreat with Hot Tub
$527 per night
SUPERHOST
  1. Entire place
  2. West Stockbridge
Private Little Studio
$110 per night
SUPERHOST
  1. Entire residential home
  2. Great Barrington
Charming Housatonic Village Cape
$269 per night
SUPERHOST
  1. Entire rental unit
  2. Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
$207 per night
  1. Entire residential home
  2. Great Barrington
Farmhouse with views nestled among nature reserve
$347 per night
SUPERHOST
  1. Entire residential home
  2. West Stockbridge
Peaceful Stockbridge Cabin in the Woods
$250 per night
SUPERHOST
  1. Entire residential home
  2. West Stockbridge
CHARMING, VIEWS For Miles, Come RELAX, Go Hiking!
$143 per night
SUPERHOST
  1. Entire residential home
  2. Great Barrington
Morgan's Millhouse (Back)
$84 per night
SUPERHOST
  1. Entire residential home
  2. West Stockbridge
West Stockbridge MA gem, in town and facing lake
$225 per night
SUPERHOST
  1. Entire guest suite
  2. Stockbridge
Cozy and Private Modern Farmhouse Apartment
$120 per night
  1. Entire rental unit
  2. Great Barrington
The Treehouse
$109 per night