Winsted Vacation Rentals, Houses & More


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Beautiful Lake House - Magnificent in all 4 Seasons 3 Bed, 2 Bath

  • 3
  • 6
  • Min stay varies

$225

Details

Great rentals within 30 miles that match your search

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1 / 12

Quiet first floor apartment in Torrington

  • 1
  • 2
  • 2 nights min

$90

Details

1 / 44

COMFY COZY 5 BEDROOM HOME - 2 WOODED PRIVATE ACRES

  • 5
  • 10
  • 2 nights min

$395

Details

1
1 / 17

5BR Woodridge Lake Rental House

  • 5
  • 12
  • 7 nights min

$158

Details

1 / 26

NEW! 3BR Litchfield House on Half Acre of Land!

  • 3
  • 7
  • Min stay varies

$235

Details

1 / 13

Short Walk to Lake, Peaceful Getaway, Scenic Views

  • 3
  • 6
  • 2 nights min

$170

Details

3
1 / 23

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

  • 2
  • 6
  • 2 nights min

$150

Details

1 / 13

Quiet Country Contemporary Home on 5 Private Acres

  • 3
  • 10
  • 2 nights min

$375

Details

1 / 21

Prana Residence - Spa

  • 3
  • 7
  • 2 nights min

$750

Details

1
1 / 11

Riverwood - Cozy Carriage House in the Woods

  • 1
  • 2
  • 2 nights min

$165

Details

1 / 54

New! 3BR Cornwall Bridge Villa w/Spa & Indoor Pool

  • 3
  • 7
  • Min stay varies

$650

Details

18
1 / 11

The Cottage at Great Falls

  • 2
  • 4
  • 2 nights min

$200

Details

1 / 27

Country Estate newly renovated that sleeps 16!

  • 5
  • 16
  • Min stay varies

$225

Details

1 / 13

Mansion & Private 3.5 Acre Estate

  • 4
  • 8
  • Min stay varies

$800

Details

1
1 / 37

Charming 2+2 Lakeside Cottage on Best Lake in CT

  • 2
  • 4
  • Min stay varies

$180

Details

4
1 / 10

Apple Cottage

  • 3
  • 8
  • 1 night min

$375

Details

1 / 57

‘Carriage House’ Lakefront Warren 7BR on 25 Acres!

  • 7
  • 16
  • 4 nights min

$795

Details

1 / 10

Country Victorian Serenity in the Berkshires

  • 4
  • 6
  • 7 nights min

$229

Details

1 / 16

Wits End Farm

  • 6
  • 12
  • 3 nights min

$900

Details

1 / 14

Wits End Farm B&B

  • 5
  • 10
  • Min stay varies

$800

Details

3
1 / 42

4 Bedroom Furnished House in Lakeville Connecticut

  • 4
  • 8
  • Min stay varies

$325

Details

1 / 23

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

  • 3
  • 6
  • Min stay varies

$350

Details

1 / 24

NEW! 3BR New Preston Cottage - Lakefront w/ Dock!

  • 3
  • 6
  • Min stay varies

$256

Details

1
1 / 23

Rhubarb Hill, a Charming 1850's Farmhouse

  • 3
  • 6
  • 3 nights min

$250

Details

1
1 / 14

The perfect Southern Berkshire winter vacation esc

  • 4
  • 10
  • 7 nights min

$500

Details

1 / 22

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

  • 6
  • 14
  • 7 nights min

$600

Details

1 / 20

Renovated Barn

  • 3
  • 6
  • Min stay varies

$350

Details

1 / 24

Beautiful Lakefront Berkshire Rental

  • 5
  • 6
  • 7 nights min

$350

Details

1 / 30

South Street 4-BR Cottage with Heated Pool

  • 4
  • 8
  • Min stay varies

$696

Details

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1 / 16

Berkshires House, 40 wooded acres, Lake Frontage

  • 3
  • 8
  • Min stay varies

$175

Details

1 / 19

Restored Horse Barn On 13 Acres With Private Pond

  • 4
  • 10
  • 4 nights min

$1500

Details

1 / 13

Designer Loft Style Residence

  • 3
  • 6
  • 7 nights min

$450

Details

1 / 23

Spacious Lakeside Berkshire Home

  • 4
  • 10
  • Min stay varies

$400

Details

1
1 / 30

Lakefront 2BR Great Barrington Area Cottage w/Deck

  • 2
  • 4
  • Min stay varies

$185

Details

1 / 25

Berkshire Estate: Exquisitely furnished 6,700sf

  • 6
  • 12
  • 7 nights min

$643

Details

1 / 12

Fabulous Post & Beam Berkshire Rental

  • 7
  • 21 nights min

$179

Details

1 / 27

Enchanted Cottage on Babbling Brook

  • 3
  • 6
  • Min stay varies

$250

Details

1 / 4

Exclusive Rental in Beautiful Amenia!

  • 3
  • 6
  • 30 nights min

$134

Details

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