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Stockbridge vacation rentals

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Top-rated vacation rentals in Stockbridge

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

SUPERHOST
  1. Entire home
  2. Lee
Berkshire Mountain retreat with Urban eco-luxuries

600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relax by the firepit- we hope you enjoy your stay and will visit us again.

$394 per night
SUPERHOST
  1. Entire home
  2. Stockbridge
Bright Stockbridge country home, near everything!

Berkshires charm in this fully renovated 1800's post and beam farmhouse set on 5 park-like acres. Features open plan living/dining/kitchen with gas cooktop and gas 3 sided fireplace, lovely sun room, master suite downstairs and 2 br, bath and sitting area upstairs. Spacious deck overlooking the expansive property Conveniently located between the charming towns of Stockbridge, Lenox & Great Barrington. We are surrounded by 4 ski areas, the closest is 10 minutes away! Many dining options too.

$202 per night
SUPERHOST
  1. Entire rental unit
  2. Stockbridge
Holmes Suite: PRIME Downtown Stockbridge

Iconic and historic residences on Main St in Stockbridge. This one bedroom suite is one of three separate apartments in this large house. Walk out the front door and you are in downtown Stockbridge. There is a coffee shop/bakery two doors away, a beautiful public library directly across the street, shops, restaurants and cafes. Roomy 860 sq ft apartment with large, light filled living room, a well equipped kitchen, a king bed and a bathroom with a tub/shower.

$218 per night

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Other great vacation rentals in Stockbridge

SUPERHOST
  1. Entire guest suite
  2. Stockbridge
Cozy and Private Modern Farmhouse Apartment
$149 per night
SUPERHOST
  1. Entire guesthouse
  2. Lenox
Lenox - Sunny cottage nestled in the garden
$110 per night
  1. Entire place
  2. West Stockbridge
Private Little Studio
$129 per night
SUPERHOST
  1. Entire cottage
  2. Stockbridge
Romantic, Chic Interlaken Cottage Stockbridge
$292 per night
SUPERHOST
  1. Entire home
  2. Stockbridge
Sun-filled, Charming Stockbridge Classic- In Town!
$278 per night
SUPERHOST
  1. Entire guest suite
  2. South Lee
Sunny Riverside Apartment
$134 per night
  1. Entire cottage
  2. Stockbridge
Rustic Berkshires Cottage
$275 per night
SUPERHOST
  1. Entire home
  2. West Stockbridge
West Stockbridge MA gem, in town and facing lake
$250 per night
SUPERHOST
  1. Entire cottage
  2. Great Barrington
Artist Cottage at the foot of Monument Mountain
$257 per night
  1. Entire chalet
  2. Richmond
Berkshire Mountain Getaway
$150 per night
  1. Entire home
  2. Lenox
Cozy Lakeside Cottage
$125 per night
SUPERHOST
  1. Private room
  2. Great Barrington
Quiet refuge in Great Barrington
$50 per night