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 / 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 / 10

Heart of Lenox

  • 2
  • 4
  • Min stay varies

$176

Details

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 9

Bentley Brook 2 bedroom 2 bathroom

  • 2
  • 8
  • 2 nights min

$67

Details

1 / 14

2200sf Country House on 16 Acres-2 Miles to Jiminy

  • 4
  • 9
  • 2 nights min

$226

Details

1 / 17

Whitman Woods: Private Berkshire Vacation, 4 acre

  • 4
  • 8
  • 1 night min

$100

Details

1 / 25

LUXURY FOX HOLLOW ESTATE HOME ON LAUREL LAKE

  • 5
  • 14
  • 2 nights min

$450

Details

1 / 24

Perfect Getaway for Body, Mind and Soul

  • 3
  • 5
  • 7 nights min

$237

Details

1 / 8

Valley View

  • 1
  • 3
  • Min stay varies

$77

Details

1 / 12

July4th Berkshires/James Taylor/2Bed Presidential

  • 2
  • 6
  • 2 nights min

$376

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$150

Details

1 / 6

Jiminy Peak Ski Resort-Country Village's Best Unit

  • 2
  • 6
  • 1 night min

$250

Details

1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$201

Details

1 / 17

One of the Finest Homes and Best location in the Berkshires

  • 4
  • 10
  • 3 nights min

$501

Details

1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$201

Details

1 / 49

Romantic Lakefront Mountain Hideaway

  • 3
  • 8
  • 1 night min

$248

Details

1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

1 / 14

Christmas in The Berkshires

  • 1
  • 4
  • 2 nights min

$176

Details

1 / 17

House On Main Street

  • 4
  • 16
  • Min stay varies

$445

Details

1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 24

Berkshires Waterfront Lakehouse Sanctuary

  • 3
  • 6
  • 2 nights min

$196

Details

1 / 31

3 BR apartment, walking distance to Mass MoCa

  • 3
  • 15
  • Min stay varies

$166

Details

1 / 13

Jiminy Peak Mountain Resort - Luxury Ski In Ski Out Home

  • 2
  • 7
  • Min stay varies

$219

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 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • Min stay varies

$326

Details

1 / 23

Renovated 2 bedroom in Heart of Lenox

  • 2
  • 4
  • Min stay varies

$300

Details

1 / 8

Spacious Newly Renovated 2 BR Cono walk to town

  • 2
  • 6
  • 30 nights min

$100

Details

1 / 21

Wyndham Bentley Brook at Jiminy Peak

  • 2
  • 6
  • 2 nights min

$250

Details

1 / 12

A Cute 2 Bedroom House Near Downtown Lenox

  • 2
  • 5
  • Min stay varies

$150

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

1 / 7

Deluxe New Home, 2 Master Suites, Tanglewood Area

  • 5
  • 12
  • 3 nights min

$750

Details

1 / 6

Thanksgiving week lux condo/4 Berkshires

  • 2
  • 4
  • 7 nights min

$229

Details

1 / 5

Berkshire Mountain Lodge - Fri, Sat,Sun check ins only! Inbox x

  • 1
  • 4
  • 7 nights min

$157

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$630

Details

1 / 14

Perfect for skiers in the Berkshires

  • 3
  • 6
  • Min stay varies

$100

Details

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