Search results; Over 1,000 homes in Winchester

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Guest favorite
Home in Winsted
Spacious & serene house in Berkshires
8 guests4 bedrooms5 beds3.5 baths
Aug 23 – 28
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Aug 23 – 28
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ﺩ.ﺇ8,826 for 5 nights

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Guest favorite
Apartment in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
Aug 17 – 22
ﺩ.ﺇ1,959 for 5 nights
4.9 out of 5 average rating, 105 reviews
Guest favorite
Apartment in Winchester
Gateway to the Berkshires
5 beds
Aug 23 – 28
ﺩ.ﺇ2,626 for 5 nights
4.91 out of 5 average rating, 388 reviews
Guest favorite
Apartment in Winsted
Haven at Highland lake
2 beds
Sep 2 – 7
ﺩ.ﺇ2,153 for 5 nights
4.89 out of 5 average rating, 114 reviews
Guest favorite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
4 beds
Aug 22 – 27
ﺩ.ﺇ8,589 for 5 nights
5.0 out of 5 average rating, 12 reviews
Guest favorite
Apartment in Winsted
1st Floor The Inn at Highland Lake
2 beds
Sep 7 – 12
ﺩ.ﺇ3,229 for 5 nights
4.87 out of 5 average rating, 39 reviews
Apartment in Winsted
“Hidden Gem | Fully Private ”
2 queen beds
Aug 17 – 22
ﺩ.ﺇ3,423 for 5 nights
4.74 out of 5 average rating, 27 reviews
Top guest favorite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
Aug 31 – Sep 5
ﺩ.ﺇ2,761 for 5 nights
4.96 out of 5 average rating, 169 reviews
Home in Winsted
Renovated lake house, just steps to the water.
4 beds
Aug 24 – 29
ﺩ.ﺇ3,660 for 5 nights
4.75 out of 5 average rating, 36 reviews
Guest favorite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
Sep 3 – 8
ﺩ.ﺇ3,388 for 5 nights
4.92 out of 5 average rating, 62 reviews
Guest favorite
Room in New Hartford
Stay with MarthaHosting for 6 years,
The West End Retreat Rm #2 - New Hartford, CT
Aug 18 – 23
ﺩ.ﺇ1,938 for 5 nights
4.94 out of 5 average rating, 63 reviews
Guest favorite
Room in New Hartford
Stay with MarthaHosting for 6 years,
The West End Retreat Rm #1, New Hartford, CT
Aug 17 – 22
ﺩ.ﺇ1,938 for 5 nights
4.83 out of 5 average rating, 70 reviews
Top guest favorite
Guest suite in Simsbury
Powder Forest Guest House Room 1
2 beds
Aug 24 – 29
ﺩ.ﺇ2,906 for 5 nights
5.0 out of 5 average rating, 53 reviews
Guest favorite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 beds
Sep 3 – 8
ﺩ.ﺇ2,777 for 5 nights
4.94 out of 5 average rating, 35 reviews
Guest favorite
Room in New Hartford
Stay with MarthaHosting for 6 years,
The West End Retreat Suite 4, New Hartford, CT
Aug 18 – 23
ﺩ.ﺇ2,799 for 5 nights
5.0 out of 5 average rating, 16 reviews
Room in Simsbury
Stay with Audrey
Cozy suite with office space in Simsbury
Aug 22 – 27
ﺩ.ﺇ1,572 for 5 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Farm stay in West Simsbury
Flamig Farm Staycation
4 beds
Sep 7 – 12
ﺩ.ﺇ3,595 for 5 nights
4.96 out of 5 average rating, 498 reviews
Top guest favorite
Room in Norfolk Historic District
Stay with Bill And PamelaArtist,
Maple House, Birch Room
Aug 18 – 23
ﺩ.ﺇ3,531 for 5 nights
4.98 out of 5 average rating, 46 reviews
Guest favorite
Cabin in New Hartford
West Hill Cabin
4 beds
Sep 1 – 6
ﺩ.ﺇ7,767 for 5 nights
4.98 out of 5 average rating, 52 reviews