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Vacation rentals in Stockbridge

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Top-rated vacation rentals in 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
Main Street Delight - One Bedroom Apartment
SUPERHOST
Entire rental unit · 4 guests · 1 bed · 1 bath
Main Street Delight - One Bedroom ApartmentLocated on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for four, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a Smart TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.
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.

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Other great vacation rentals in Stockbridge

SUPERHOST
  1. Entire residential home
  2. Lee
Berkshire Mountain retreat with Urban eco-luxuries
$311 per night
SUPERHOST
  1. Entire cabin
  2. Stockbridge
NEW Stockbridge Cabin - A quick stroll to the lake
$249 per night
SUPERHOST
  1. Entire residential home
  2. Lenox
Private NE Colonial walking distance to Lenox.
$275 per night
SUPERHOST
  1. Entire rental unit
  2. Stockbridge
Historic,Famous,Iconic, Unforgettable Berks Escape
$207 per night
SUPERHOST
  1. Entire residential home
  2. Lenox
The Berkshire Quintessential Cape downtown Lenox
$357 per night
  1. Entire residential home
  2. West Stockbridge
[NEW] Sunny 4BR, mins to Skiing, Tanglewood & Bowl
$450 per night
SUPERHOST
  1. Entire residential home
  2. Stockbridge
Bright Stockbridge country home, close to skiing!
$150 per night
SUPERHOST
  1. Entire residential home
  2. Great Barrington
Charming Housatonic Village Cape
$261 per night
SUPERHOST
  1. Entire residential home
  2. West Stockbridge
Berkshires Forest Retreat with Hot Tub
$493 per night
SUPERHOST
  1. Entire condominium (condo)
  2. Lenox
Heart of Lenox!! - Renovated downtown apartment
$298 per night
SUPERHOST
  1. Entire residential home
  2. Stockbridge
Cozy cottage by the brook
$157 per night
SUPERHOST
  1. Entire place
  2. West Stockbridge
Private Little Studio
$110 per night