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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Compare 52 Cottages in Winsted with updated reviews, rates, and availability.

West Cornwall Cabin ~ 4 Mi to Covered Bridge!
House (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

3.0 star property
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Peaceful Goshen Cottage w/ Screened Porch & Views!
Cottage (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Peaceful Goshen Cottage w/ Screened Porch & Views!

3.0 star property
Peaceful Goshen Cottage w/ Screened Porch & Views!
Lakefront Granby Escape w/ Private Dock & Kayaks!
House (2 Bedrooms) | Interior

Lakefront Granby Escape w/ Private Dock & Kayaks!

3.0 star property
Lakefront Granby Escape w/ Private Dock & Kayaks!
Modern Terryville Cottage w/ Deck & Lake View!
Cottage (2 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Modern Terryville Cottage w/ Deck & Lake View!

3.0 star property
10.0 out of 10, Exceptional, (1)
Modern Terryville Cottage w/ Deck & Lake View!
Charming Sharon Dwelling w/ Deck & Fire Pit!
Interior

Charming Sharon Dwelling w/ Deck & Fire Pit!

3.0 star property
Charming Sharon Dwelling w/ Deck & Fire Pit!
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Interior

Cozy Litchfield House w/ Fenced-in Yard & Fire Pit

3.0 star property
Cozy Litchfield House w/ Fenced-in Yard & Fire Pit
Skiing & Hiking: Water-view Home in the Berkshires
Outdoor dining

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Spacious & Modern Ashley Falls Home on 1 Acre
House (5 Bedrooms) | Interior

Spacious & Modern Ashley Falls Home on 1 Acre

3.0 star property
8.0 out of 10, Very Good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Spacious & Modern Ashley Falls Home on 1 Acre
Serene Salisbury Rental Home on 26 Acres w/ Deck!
House (6 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Serene Salisbury Rental Home on 26 Acres w/ Deck!

3.0 star property
Serene Salisbury Rental Home on 26 Acres w/ Deck!
Dainty New Preston Cottage w/ Dock & Lake Views!
Interior

Dainty New Preston Cottage w/ Dock & Lake Views!

3.0 star property
Dainty New Preston Cottage w/ Dock & Lake Views!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Historic Huntington Home - Walk to Westfield River
House (3 Bedrooms) | Private kitchen | Microwave, oven, stovetop, dishwasher

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Modern Escape w/ Fire Pit, Near Lake Waramaug
TV

Modern Escape w/ Fire Pit, Near Lake Waramaug

3.0 star property
Modern Escape w/ Fire Pit, Near Lake Waramaug
Lakefront Otis Home w/ Stunning Views & Boats!
Aerial view

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Becket Home w/ 3-season Porch: Walk to Lake Access
Interior

Becket Home w/ 3-season Porch: Walk to Lake Access

3.0 star property
Becket Home w/ 3-season Porch: Walk to Lake Access
Charming Farmington Home ~ 5 Mi to Uconn Health!
Interior

Charming Farmington Home ~ 5 Mi to Uconn Health!

3.0 star property
Charming Farmington Home ~ 5 Mi to Uconn Health!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
TV, fireplace

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Forget-me-not by Avantstay Bold Lakefront Escape
Interior

Forget-me-not by Avantstay Bold Lakefront Escape

3.0 star property
Forget-me-not by Avantstay Bold Lakefront Escape
'the Mill River Cabin w/ Fireplace & River View!
Interior

'the Mill River Cabin w/ Fireplace & River View!

3.0 star property
'the Mill River Cabin w/ Fireplace & River View!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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