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Areas near Stockbridge

Travelers going to Stockbridge are booking October dates now. Secure your vacation rental today and have the perfect trip.

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 30

Tranquil 3BR Stockbridge House w/Private Deck

  • 3
  • 6
  • Min stay varies

$216

Details

1 / 26

3BD Newly Rennovated Contempoary Near Stockbridge

  • 3
  • 6
  • 3 nights min

$300

Details

1 / 32

Beautiful New Construction Vacation Home

  • 4
  • 12
  • Min stay varies

$500

Details

1 / 6

Rustic Rivers end room in the barn at chestnut lodge

  • 1
  • 4
  • 2 nights min

$155

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$475

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 47

Jacob's Tanglewood Ranch (great for groups 10+)

  • 5
  • 20
  • Min stay varies

$1000

Details

1 / 22

Vacation Home on 10 Acres with Pool and Spa

  • 3
  • 6
  • 7 nights min

$501

Details

1 / 17

Restored 1886 Eyebrow Colonial

  • 2
  • 6
  • 7 nights min

$214

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 24

NEW! 2BR Stockbridge Home - Walk To Golf Course!

  • 2
  • 6
  • Min stay varies

$211

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$150

Details

1 / 35

Stockbridge Country Inn

  • 8
  • 17
  • 3 nights min

$971

Details

1 / 12

Fabulous NEW Spacious House in the Berkshires Tanglewood

  • 4
  • 8
  • 2 nights min

$450

Details

1 / 16

Beautifully Renovated Berkshires Farmhouse

  • 2
  • 4
  • 2 nights min

$211

Details

1 / 17

One of the Finest Homes and Best location in the Berkshires

  • 4
  • 10
  • 3 nights min

$501

Details

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