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36 Houses

20

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

Connecticut / Winsted

Winsted house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$258

Responds fast!
avg. 2 hours 42 minutes

Price per night from

$258

Great rentals within 20 miles that match your search

Distance approx 17.64 km from Winsted

(1) Excellent 

20

Enjoy horses and the largest recreational lake in Massachusetts

Berkshires / East Otis

East Otis apartment

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$126

Price per night from

$126

Distance approx 19.59 km from Winsted

(1) Excellent 

13

Lake House

Connecticut / Lakeville

Lakeville house

5 9 2 nights min

  • 5 bedrooms
  • sleeps 9
  • 2 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$687

Price per night from

$687

Distance approx 18.6 km from Winsted

32

Berkshire Home on Lake Garfield w/Dock & Boats

Berkshires / Monterey

Monterey house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$344

Responds fast!
avg. 7 minutes

Price per night from

$344

Distance approx 17.68 km from Winsted

(1) Excellent 

37

Charming 2+2 Lakeside Cottage on Best Lake in CT

Connecticut / Salisbury

Salisbury cottage

2 4 30 nights min

  • 2 bedrooms
  • sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child Friendly

Price per night from

$207

Price per night from

$207

Distance approx 8.2 km from Winsted Show on Map

(6) Excellent 

12

Quiet first floor apartment in Torrington

Connecticut / Torrington

Torrington apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min

Price per night from

$103

Price per night from

$103

Distance approx 15.68 km from Winsted

(19) Excellent 

18

The Cottage at Great Falls

Connecticut / Falls Village

Falls Village cottage

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
“Relaxation Overload” Went with the girlfriend for a weekend getaway and chose the perfect place. Extremely relaxing and soothing trip. Everything you need is there, french press? Yep. Towels? Yep. Amazing art? Yep! This place is incredibly decorated a
…see more

Price per night from

$275

Responds fast!
avg. 1 hour 35 minutes

Price per night from

$275

Distance approx 19.35 km from Winsted

(3) Excellent 

42

4 Bedroom Furnished House in Lakeville Connecticut

Connecticut / Lakeville

Lakeville house

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Ask about pets

Price per night from

$373

Price per night from

$373

Distance approx 16.6 km from Winsted

24

Prana Residence - Spa

Connecticut / Cornwall Bridge

Cornwall Bridge house

3 7 2 nights min

  • 3 bedrooms
  • sleeps 7
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$859

Price per night from

$859

Distance approx 15.22 km from Winsted

(1) Excellent 

11

Riverwood - Cozy Carriage House in the Woods

Connecticut / Falls Village

Falls Village apartment

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$258

Price per night from

$258

Distance approx 17.12 km from Winsted

10

Country Victorian Serenity in the Berkshires

Berkshires / New Marlborough

New Marlborough house

4 6 7 nights min

  • 4 bedrooms
  • sleeps 6
  • 7 nights min
  • Suitable for children age 5+
  • Private garden

Price per night from

$263

Price per night from

$263

Distance approx 19.27 km from Winsted

24

Beautiful Lakefront Berkshire Rental

Berkshires / Monterey

Monterey house

5 6 7 nights min

  • 5 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Air conditioning

Price per night from

$489

Responds fast!
avg. 3 hours 33 minutes

Price per night from

$489

Distance approx 10.73 km from Winsted

24

Waterfront Home in Tolland w/ Deck - Steps to Lake

Connecticut / West Hartland

West Hartland log cabin

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$252

Responds fast!
avg. 7 minutes

Price per night from

$252

Distance approx 17.17 km from Winsted

(5) Excellent 

10

Apple Cottage

Berkshires / Sheffield

Sheffield farmhouse

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Ask about children
  • Air conditioning
  • Private garden

Price per night from

$430

Responds fast!
avg. 3 hours 22 minutes

Price per night from

$430

Distance approx 13.88 km from Winsted

(1) Excellent 

24

Litchfield House on Half Acre - 1 Mile to Town!

Connecticut / Litchfield

Litchfield house

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$243

Responds fast!
avg. 15 minutes

Price per night from

$243

Distance approx 18.23 km from Winsted

22

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Berkshires / Otis

Otis house

6 14 7 nights min

  • 6 bedrooms
  • sleeps 14
  • 7 nights min
  • Ask about children
  • Ask about pets

Price per night from

$687

Price per night from

$687

Distance approx 9.16 km from Winsted

24

Cozy Canton Home w/Porch & Sauna Near Ski Sundown!

Connecticut / Canton

Canton house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Ski
  • Child Friendly
  • Air conditioning

Price per night from

$178

Responds fast!
avg. 14 minutes

Price per night from

$178

Distance approx 19.79 km from Winsted

27

Country Estate newly renovated that sleeps 16!

Connecticut / Bethlehem

Bethlehem house

5 16 3 nights min

  • 5 bedrooms
  • sleeps 16
  • 3 nights min
  • Child Friendly

Price per night from

$258

Responds fast!
avg. 20 minutes

Price per night from

$258

Distance approx 14.93 km from Winsted

(1) Excellent 

21

Three-bedroom one-and-a-half bath ranch with lots of room inside and outside

Connecticut / Granby

Granby house

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$172

Responds fast!
avg. 3 hours 11 minutes

Price per night from

$172

Distance approx 11.41 km from Winsted

(1) Excellent 

26

Windy Top Stone Cottage

Connecticut / North Granby

North Granby cottage

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$110

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$110

Distance approx 16.72 km from Winsted

35

Charming Private Guest Suite in Historic Village in the Berkshires

Berkshires / New Marlborough

New Marlborough studio

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min

Price per night from

$109

Price per night from

$109

Distance approx 9.18 km from Winsted

44

COMFY COZY 5 BEDROOM HOME - 2 WOODED PRIVATE ACRES

Connecticut / Hartford

Hartford house

5 10 2 nights min

  • 5 bedrooms
  • sleeps 10
  • 2 nights min
  • Child Friendly

Price per night from

$453

Price per night from

$453

Distance approx 16.34 km from Winsted

24

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

Berkshires / Otis

Otis log cabin

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$115

Responds fast!
avg. 7 minutes

Price per night from

$115

Distance approx 15.39 km from Winsted

13

Quiet Country Contemporary Home on 5 Private Acres

Connecticut / West Cornwall

West Cornwall house

3 10 2 nights min

  • 3 bedrooms
  • sleeps 10
  • 2 nights min
  • Nearest beach 6 mi
  • Child Friendly
  • Air conditioning

Price per night from

$406

Price per night from

$406

Distance approx 3.65 km from Winsted Show on Map

12

Colebrook Dream

Connecticut / Colebrook

Colebrook house

3 12 2 nights min

  • 3 bedrooms
  • sleeps 12
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$344

Price per night from

$344

Distance approx 19.02 km from Winsted

(1) Excellent 

14

The perfect Southern Berkshire winter vacation esc

Berkshires / Sheffield

Sheffield house

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$573

Price per night from

$573

Distance approx 9.41 km from Winsted Show on Map

16

Direct Waterfront Lake Home on Tranquil Harwinton

Connecticut / Harwinton

Harwinton cottage

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$226

Price per night from

$226

Distance approx 8.97 km from Winsted

24

NEW-Norfolk Countryside Home 30 Min to Ski Sundown

Connecticut / Norfolk

Norfolk house

4 5 min stay varies

  • 4 bedrooms
  • sleeps 5
  • min stay varies
  • Ski
  • Child Friendly

Price per night from

$247

Responds fast!
avg. 7 minutes

Price per night from

$247

Distance approx 18.65 km from Winsted

12

Cottage on East Twin Lakes, Internet Access, A/C.

Connecticut / Salisbury

Salisbury cottage

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$180

Price per night from

$180

Distance approx 19.69 km from Winsted

21

Washington - "Senff 8-BR Estate" Heated Pool, Private Scenic Estate Neighborhood

Connecticut / Washington

Washington house

8 14 min stay varies

  • 8 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 5 mi
  • Swimming pool
  • Child Friendly

Price per night from

$341

Price per night from

$341

Distance approx 18.34 km from Winsted

17

Picturesque 19th century home on 3 private acres

Berkshires / New Marlborough

New Marlborough house

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child Friendly
  • Private garden

Price per night from

$172

Price per night from

$172

Distance approx 19.7 km from Winsted

36

100% ROXBURY (Zoom in Map+) PoshPadsCT "PAINTER RIDGE" Mint 3BR, Pool, BBQ,Bikes

Connecticut / Washington

Washington house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Pet Friendly

Price per night from

$264

Price per night from

$264

Distance approx 12.46 km from Winsted

31

Connecticut Wine Country Getaway!

Connecticut / North Granby

North Granby apartment

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Air conditioning
  • Private garden

Price per night from

$132

Responds fast!
avg. 2 hours 30 minutes

Price per night from

$132

Distance approx 17.72 km from Winsted

13

Mansion & Private 3.5 Acre Estate

Connecticut / Bloomfield

Bloomfield manor house

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning

Price per night from

$801

Responds fast!
avg. 3 hours 52 minutes

Price per night from

$801

Distance approx 15.19 km from Winsted

(3) Very Good 

22

Comfortable Rustic Cottage on 4 Wooded Acres with Brook

Connecticut / West Cornwall

West Cornwall cottage

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 12 mi
  • Child Friendly
  • Air conditioning

Price per night from

$172

Price per night from

$172

Distance approx 17.7 km from Winsted

11

Evie's Turning Point Farm

Connecticut / Warren

Warren farmhouse

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$149

Price per night from

$149