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 / 32

Escape to the Berkshires!

  • 4
  • 8
  • 2 nights min

$275

Details

1 / 11

Overnight at Althouse -Higgins

  • 2
  • 4
  • 2 nights min

$176

Details

1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$125

Details

1 / 23

Escape to Lakeville CT ** Lime Rock *August Dates available* Hotchkiss

  • 3
  • 6
  • Min stay varies

$351

Details

1 / 37

Charming 2+2 Lakeside Cottage on Best Lake in CT

  • 2
  • 4
  • Min stay varies

$181

Details

1 / 15

Newly Renovated Vacation Home near Catamount Ski

  • 3
  • 10
  • Min stay varies

$300

Details

1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$501

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$150

Details

1 / 32

RIVERSONG "PENTHOUSE"

  • 1
  • 2
  • 1 night min

$129

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1700

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$351

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$201

Details

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$134

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 15

Outdoor getaway hunting,fishing,skiing..relaxation

  • 3
  • 9
  • 2 nights min

$191

Details

1 / 13

Berkshires: Romantic Cottage with spectacular view

  • 1
  • 3
  • Min stay varies

$226

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 31

Beautifully decorated & immaculate log chalet

  • 3
  • 6
  • 2 nights min

$176

Details

1 / 19

Lake House in the Berkshires

  • 3
  • 8
  • 1 night min

$376

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 58

Country estate on 100 acres perfect for families

  • 4
  • 6
  • 7 nights min

$993

Details

1 / 25

NEW! Charming 3BR Great Barrington House by River!

  • 3
  • 8
  • Min stay varies

$206

Details

1 / 30

Gem of the Berkshires, walk to downtown & lake.

  • 5
  • 12
  • 2 nights min

$401

Details

1 / 24

Country Elegance in the Berkshires

  • 4
  • 12
  • 2 nights min

$651

Details

1 / 27

Shaker Hill

  • 5
  • 10
  • 3 nights min

$475

Details

1 / 15

S. Berkshires Mountain Treehouse • Views • Privacy

  • 2
  • 4
  • 14 nights min

$243

Details

1 / 13

Lakefront Berkshires Ski/Summer House, Great Views

  • 4
  • 10
  • 2 nights min

$188

Details

1 / 16

Cill Aodain Cabin

  • 1
  • 2
  • 2 nights min

$181

Details

1 / 25

Berkshire Estate: Exquisitely furnished 6,700sf

  • 6
  • 12
  • 7 nights min

$644

Details

1 / 10

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

  • 2
  • 4
  • 3 nights min

$196

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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