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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.

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West Stockbridge MA gem, in town and facing lake

In an enchanting Berkshire village, this small West Stockbridge house makes a big architectural statement. It's within walking distance of 5 restaurants, 2 galleries, small shops and a food store. Tanglewood, Kripalu, Hancock Shaker Village, Great Barrington: 15 min away. MassMoca and The Clark: 45 minutes away. Close to skiing at Butternut, Jiminy Peak and Catamount.

$250 per night
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Rustic Modern Retreat

Discover the Berkshires in this modern, rustic cottage. Just a mile from the center of West Stockbridge, you'll be in the perfect location to enjoy hiking, kayaking, skiing, Lenox, and Tanglewood. Set in a beautiful location, this 3 BR home is the perfect place to relax and unwind in the country. The main floor is open and airy, and outdoor spaces include a large deck, grill, and fire pit.

$296 per night
  1. Entire home
  2. West Stockbridge
The Filomena: Historical charm + modern design

We are fully booked at the moment but we release openings on IG (thefilomena)! "The coolest AirBnb in Massachusetts" - Conde Nast Traveler Completely renovated with 13 ft ceilings, a working fireplace, chef's kitchen, & spacious bedrooms, the Filomena makes the perfect Berkshires getaway for friends & families. Set on an acre+, the house has a large yard & side porch, is a 2 minute walk from shops & restaurants in town, & minutes to Tanglewood.

$800 per night

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Other great vacation rentals in West Stockbridge

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Historic 1810 Farmhouse - Fully Renovated
$291 per night
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  2. Stockbridge
Bright Stockbridge country home, near everything!
$191 per night
  1. Entire condo
  2. West Stockbridge
Modern & Comfy, 5★ Location ♛ 2BR Queen Bed ☀ Yard
$160 per night
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  2. Austerlitz
Fog Hill Cabin Wooded Getaway to the Berkshires
$164 per night
  1. Entire chalet
  2. Richmond
Berkshire Mountain Getaway
$150 per night
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  2. West Stockbridge
Loft Style Home, West Stockbridge, Book Now!
$266 per night
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  2. Stockbridge
Romantic, Chic Interlaken Cottage Stockbridge
$292 per night
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  2. Canaan
Airy cottage with meadow views in The Berkshires
$160 per night
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  2. West Stockbridge
Heart of the Berkshires - Bright, Cozy, Near Lake
$450 per night
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  1. Entire guest suite
  2. Stockbridge
Cozy and Private Modern Farmhouse Apartment
$148 per night
  1. Entire cottage
  2. Stockbridge
Rustic Berkshires Cottage
$275 per night
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  2. West Stockbridge
Tanglewood Cottage in the heart of the Berkshires
$300 per night