Cheshire Vacation Rentals, Houses & More


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Areas near Cheshire

1 / 19

Charming Berkshires lakefront house, great views

  • 2
  • 5
  • 2 nights min

$201

Details

Great rentals within 20 miles that match your search

1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$326

Details

1 / 12

Heart of the Berkshires!

  • 3
  • 6
  • 2 nights min

$226

Details

1 / 19

Lake House

  • 5
  • 9
  • 7 nights min

$714

Details

1 / 33

Wyndham Bentley Brook Resort

  • 2
  • 8
  • 3 nights min

$61

Details

1 / 13

The Gatehouse on Golden Hill

  • 4
  • 14
  • Min stay varies

$800

Details

1 / 16

Berkshires Vacation Rental - Bentley Brook Resort Suite

  • 2
  • 6
  • 3 nights min

$200

Details

1 / 8

Writer's Room at Chestnut Lodge

  • 1
  • 2
  • 2 nights min

$201

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

Details

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

1 / 12

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

  • 1
  • 4
  • 3 nights min

$201

Details

1 / 23

Apartment walking distance to Mass MoCa!!

  • 2
  • 10
  • Min stay varies

$155

Details

1 / 4

Golden Triangle in the Berkshires

  • 2
  • 4
  • 2 nights min

$2500

Details

1 / 7

the BIG room at chestnut lodge

  • 1
  • 6
  • 2 nights min

$201

Details

1 / 13

Jiminy Peak Luxury Ski In/Ski Out Home

  • 3
  • 8
  • Min stay varies

$330

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 13

Garfield House

  • 2
  • 6
  • 2 nights min

$176

Details

1 / 49

Romantic Lakefront Mountain Hideaway

  • 3
  • 8
  • 1 night min

$248

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$150

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 25

Luxury and Amenities in a Stunning Rustic Setting

  • 4
  • 14
  • Min stay varies

$357

Details

1 / 13

Berkshires Summer Rental Beaver Pond Hancock MA

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 7 nights min

$172

Details

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

1 / 31

Big Beautiful 7 bedroom 3 bath hot tub pool table

  • 7
  • 18
  • 2 nights min

$300

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$231

Details

1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$125

Details

1 / 20

New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)

  • 3
  • 6
  • 7 nights min

$501

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 10

Vacation Village in the Berkshires Available July 22-29

  • 2
  • 8
  • 7 nights min

$157

Details

1 / 24

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$196

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1001

Details

1 / 31

3 BR apartment, walking distance to Mass MoCa

  • 3
  • 15
  • Min stay varies

$166

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 7

ROOM walking distance to Mass MoCa

  • 1
  • 2
  • 1 night min

$71

Details

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