Canaan Vacation Rentals, Houses & More


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Areas near Canaan

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1 / 19

Mountain Top - Post + Beam House

  • 3
  • 8
  • 2 nights min

$325

Details

1 / 9

Cedar Chest

  • 1
  • 2
  • 30 nights min

$92

Details

Great rentals within 30 miles that match your search

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1 / 5

Haddock Hill House

  • 1
  • 2
  • 1 night min

$160

Details

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1 / 10

Lakeview cottage with swingset & firepit!

  • 3
  • 6
  • Min stay varies

$135

Details

1 / 20

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

  • 3
  • 6
  • 7 nights min

$450

Details

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1 / 20

Enjoy Summer in The Berkshires. last minute July Dates Available. Great Location

  • 3
  • 8
  • Min stay varies

$275

Details

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1 / 10

Great Vacation House in the Berkshires on Richmond Pond

  • 2
  • 6
  • 6 nights min

$200

Details

1 / 58

Country estate on 100 acres perfect for families

  • 4
  • 6
  • 7 nights min

$1000

Details

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1 / 10

Comfortable Farmhouse in the Berkshires

  • 5
  • 12
  • 2 nights min

$325

Details

1 / 14

Modern Cozy Wooded Retreat

  • 2
  • 6
  • 30 nights min

$286

Details

1 / 23

Charming spacious country home with stunning views

  • 5
  • 14
  • 3 nights min

$1000

Details

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1 / 20

Berkshire's Getaway ---Peace & Tranquility

  • 3
  • 8
  • 2 nights min

$150

Details

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1 / 8

Cozy & Modern Home -mins from Tanglewood & Kripalu

  • 2
  • 6
  • 2 nights min

$125

Details

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1 / 20

Berkshire Farmhouse Vacation

  • 5
  • 12
  • Min stay varies

$275

Details

1 / 5

Cozy Modern Condo for the Berkshires

  • 2
  • 6
  • 2 nights min

$250

Details

4
1 / 11

Stockbridge Bowl house

  • 3
  • 8
  • 2 nights min

$225

Details

1 / 4

The Meadow House 4 bdrm 4 bath house

  • 4
  • 12
  • 2 nights min

$600

Details

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1 / 21

Cozy Cottage Private Lake Community

  • 3
  • 6
  • 2 nights min

$200

Details

6
1 / 25

Berkshire Blueberry Lodge LLC - Near Jiminy Peak

  • 4
  • 10
  • 2 nights min

$400

Details

1 / 18

Mountain Views Atop Blueberry Hill on 40 Acres

  • 3
  • 6
  • 2 nights min

$200

Details

1 / 29

Beauty in the Berkshires

  • 6
  • 14
  • 3 nights min

$1700

Details

1 / 17

One of the Finest Homes and Best location in the Berkshires

  • 4
  • 10
  • 3 nights min

$500

Details

5
1 / 16

Family-friendly Cottage Near Lake, Tanglewood

  • 3
  • 7
  • Min stay varies

$285

Details

1 / 23

The Dacha: Summer/Skiing House in the Berkshires

  • 2
  • 6
  • 3 nights min

$200

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
  • Min stay varies

$200

Details

1 / 4

Horse Room

  • 1
  • 3
  • 1 night min

$150

Details

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1 / 10

Heart of Lenox

  • 2
  • 4
  • Min stay varies

$175

Details

1 / 4

Nasturtium Room

  • 1
  • 3
  • 1 night min

$150

Details

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1 / 21

Gartner House, a charming home in Lenox

  • 4
  • 7
  • 2 nights min

$200

Details

1 / 4

Iris Room

  • 1
  • 2
  • 1 night min

$150

Details

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1 / 5

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

  • 1
  • 4
  • 7 nights min

$158

Details

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1 / 30

Tranquil 3BR Stockbridge House w/Private Deck

  • 3
  • 6
  • Min stay varies

$215

Details

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1 / 22

Berkshire Getaway at 'Tofu'S Retreat'

  • 3
  • 6
  • Min stay varies

$500

Details

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1 / 12

Heart of the Berkshires!

  • 3
  • 6
  • 2 nights min

$225

Details

1 / 22

Vacation Home on 10 Acres with Pool and Spa

  • 3
  • 6
  • 7 nights min

$500

Details

1 / 14

Perfect for skiers in the Berkshires

  • 3
  • 6
  • Min stay varies

$100

Details

1 / 30

INTERIOR DESIGNERS BOTANICAL GARDENS

  • 1
  • 5
  • Min stay varies

$150

Details

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