Great Barrington Apartments, Villas & more


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Areas near Great Barrington

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

Great rentals within 20 miles that match your search

1 / 25

Cultural Playground 2 bed, 5 minutes to Tanglewood

  • 2
  • 6
  • Min stay varies

$298

Details

1 / 9

Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate

  • 1
  • 4
  • 2 nights min

$249

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$447

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 8

Dream Guesthouse - Artist's studio, cool country chic

  • 1
  • 4
  • Min stay varies

$184

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$149

Details

1 / 10

Ranch House in Lakeside Community

  • 3
  • 6
  • 2 nights min

$199

Details

1 / 12

The Smith Farm Homestead

  • 1
  • 2
  • 2 nights min

$144

Details

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$355

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$149

Details

1 / 12

little blue cottage lots of cute! 1 mile to stockbridge center . pet friendly!

  • 1
  • 4
  • 3 nights min

$199

Details

1 / 35

Stockbridge Country Inn

  • 8
  • 17
  • 3 nights min

$963

Details

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$171

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 30

Evergreen Pines Country Estate Villa

  • 4
  • 8
  • 1 night min

$1985

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$149

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$199

Details

1 / 20

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

  • 3
  • 8
  • Min stay varies

$273

Details

1 / 2

chestnut lodge Queens Room

  • 1
  • 2
  • 2 nights min

$174

Details

1 / 13

Berkshires: Romantic Cottage with spectacular view

  • 1
  • 3
  • Min stay varies

$224

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1687

Details

1 / 10

Berkshire House Share-The Blue Room

  • 3
  • 2
  • 1 night min

$75

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$447

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 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$497

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

1 / 16

Cill Aodain Cabin

  • 1
  • 2
  • 2 nights min

$179

Details

1 / 15

S. Berkshires Mountain Treehouse • Views • Privacy

  • 2
  • 4
  • 14 nights min

$242

Details

1 / 25

NEW! Charming 3BR Great Barrington House by River!

  • 3
  • 8
  • Min stay varies

$206

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$472

Details

1 / 30

Gem of the Berkshires, walk to downtown & lake.

  • 5
  • 12
  • 2 nights min

$397

Details

1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$187

Details

1 / 10

Cozy and clean in Gt Barrington- 1 week in summer!

  • 2
  • 4
  • 3 nights min

$194

Details

1 / 25

Berkshire Estate: Exquisitely furnished 6,700sf

  • 6
  • 12
  • 7 nights min

$644

Details

1 / 9

Bershire Retreat

  • 2
  • 5
  • 2 nights min

$120

Details

1 / 6

Stunning Home! 120 Acres! Amazing!

  • 9
  • 16
  • 3 nights min

$3601

Details

1 / 18

Restored 1940s Cabin 30 Mile Views

  • 2
  • 5
  • 2 nights min

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