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Holiday rentals in Stockbridge Bowl

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Top-rated holiday rentals in Stockbridge Bowl

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

  1. Entire cottage
  2. Stockbridge
Rustic Berkshires Cottage

Lovely cottage in the heart of South County. This three season home is an authentic piece of the Berkshires. 5 minute drive from Tanglewood, 7 minute drive to Lenox, Lee, and Stockbridge, and a 4 minute walk to the town beach at the Stockbridge Bowl, it is a perfect home base for a trip to the Berkshires. Owned by our family since it was built in the 1950's, the house is rustic and filled with character and has everything you'll need for a great getaway.

  1. Entire cottage
  2. Stockbridge
Cozy hidden cottage minutes away from Tanglewood

Beautiful small private cottage, across the road from Stockbridge Bowl Lake. Easy access (1 mile ) to Tanglewood, Very short pleasant drive to Stockbridge Center and Lenox. 6 minute drive to Kripalu. 2 bedrooms each with a double bed; plus 1 bedroom (with sliding wall) with 2 single beds. Plus sleep sofa in living room. Fully furnished, full ready to use kitchen, comfortable living room, and separate large dining room with floor to ceiling glass doors, and large deck overlooking hillside.

SUPERHOST
  1. Entire cottage
  2. Stockbridge
Romantic, Chic Interlaken Cottage Stockbridge

Situated between Main Streets of Stockbridge & Lenox and steps to the Stockbridge Bowl. This jewel box cottage is a perfect place to relax. Enjoy the natural beauty of the Berkshires from the screen porch!

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Other great holiday rentals in Stockbridge Bowl

  1. Entire home
  2. Stockbridge
Lake House on Stockbridge Bowl
  1. Entire guest suite
  2. Stockbridge
Private Stockbridge Getaway
  1. Barn
  2. Stockbridge
LAKE COTTAGE -In the Berkshire/ walk to Tanglewood
SUPERHOST
  1. Entire cabin
  2. Stockbridge
Hip Stockbridge Cabin - A stroll to the lake
SUPERHOST
  1. Entire guest suite
  2. Stockbridge
Cozy and Private Modern Farmhouse Apartment
SUPERHOST
  1. Entire home
  2. Stockbridge
New Construction in Stockbridge - Lake Community
  1. Entire cottage
  2. Lenox
Stockbridge Cottage minutes from downtown Lenox
  1. Entire cabin
  2. Stockbridge
Charming Stockbridge Cabin
SUPERHOST
  1. Entire home
  2. West Stockbridge
Heart of the Berkshires - Bright, Cozy, Near Lake
SUPERHOST
  1. Entire cottage
  2. Stockbridge
*NEW* Cheerful 3 BR, 2 BA Cottage with Lake Access
  1. Entire guest house
  2. Stockbridge
Guest House in Stockbridge 3 miles to Tanglewood
  1. Private room
  2. Richmond
BLUE HEAVEN FARM; A BERKSHIRE EXPERIENCE