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Areas near Stockbridge

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

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 26

3BD Newly Rennovated Contempoary Near Stockbridge

  • 3
  • 6
  • 3 nights min

$300

Details

1 / 16

Luxury Fox Hollow Laurel Lake Ranch

  • 4
  • 11
  • Min stay varies

$501

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$300

Details

1 / 16

Family-friendly Cottage Near Lake, Tanglewood

  • 3
  • 7
  • Min stay varies

$285

Details

1 / 20

Berkshire Farmhouse Vacation

  • 5
  • 12
  • Min stay varies

$275

Details

1 / 30

Tranquil 3BR Stockbridge House w/Private Deck

  • 3
  • 6
  • Min stay varies

$216

Details

1 / 32

Beautiful New Construction Vacation Home

  • 4
  • 12
  • Min stay varies

$496

Details

1 / 6

Rustic Rivers end room in the barn at chestnut lodge

  • 1
  • 4
  • 2 nights min

$155

Details

1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$125

Details

1 / 21

The Playhouse: 7,000 Sq Feet of Berkshires Luxury

  • 6
  • 26
  • Min stay varies

$676

Details

1 / 17

Restored 1886 Eyebrow Colonial

  • 2
  • 6
  • 7 nights min

$213

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$447

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 22

Vacation Home on 10 Acres with Pool and Spa

  • 3
  • 6
  • 7 nights min

$497

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$472

Details

1 / 47

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

  • 5
  • 20
  • Min stay varies

$1000

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$149

Details

1 / 24

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

  • 2
  • 6
  • Min stay varies

$211

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$149

Details

1 / 12

Fabulous NEW Spacious House in the Berkshires Tanglewood

  • 4
  • 8
  • 2 nights min

$447

Details

1 / 35

Stockbridge Country Inn

  • 8
  • 17
  • 3 nights min

$963

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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