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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.

Great rentals within 20 miles that match your search

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$355

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$149

Details

1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$497

Details

1 / 2

chestnut lodge Queens Room

  • 1
  • 2
  • 2 nights min

$174

Details

1 / 20

Enjoy Summer in The Berkshires. last minute July and Aug dates . Great Location

  • 3
  • 8
  • Min stay varies

$273

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$447

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$66

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 10

Ranch House in Lakeside Community

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 10

Berkshire House Share-The Blue Room

  • 3
  • 2
  • 1 night min

$75

Details

1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$144

Details

1 / 9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

  • 1
  • 4
  • 2 nights min

$249

Details

1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$187

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$472

Details

1 / 18

Hillhouse Log Cabin

  • 3
  • 13
  • 2 nights min

$422

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$60

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$229

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1687

Details

1 / 6

Jiminy Peak Ski Resort-Country Village's Best Unit

  • 2
  • 6
  • 1 night min

$249

Details

1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$235

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$134

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$447

Details

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$298

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 / 16

Family-friendly Cottage Near Lake, Tanglewood

  • 3
  • 7
  • Min stay varies

$283

Details

1 / 22

Vacation Home on 10 Acres with Pool and Spa

  • 3
  • 6
  • 7 nights min

$497

Details

1 / 26

3BD Newly Rennovated Contempoary Near Stockbridge

  • 3
  • 6
  • 3 nights min

$300

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 17

Restored 1886 Eyebrow Colonial

  • 2
  • 6
  • 7 nights min

$213

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$149

Details

1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$226

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$149

Details

1 / 24

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

  • 2
  • 6
  • Min stay varies

$211

Details

1 / 35

Stockbridge Country Inn

  • 8
  • 17
  • 3 nights min

$963

Details

1 / 12

Fabulous NEW Spacious House in the Berkshires Tanglewood

  • 4
  • 8
  • 2 nights min

$447

Details

1 / 17

One of the Finest Homes and Best location in the Berkshires

  • 4
  • 10
  • 3 nights min

$497

Details

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