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Search results; Over 1,000 homes in Winsted, Winchester

Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
23–28 Aug
,
4.87 out of 5 average rating, 175 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 40 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
10–15 Aug
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
4.97 out of 5 average rating, 225 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.92 out of 5 average rating, 142 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Superhost
Cabin in New Hartford
West Hill Cottage-stroll to pristine beach
3 bedrooms, 4 beds, 1.5 bathrooms
10–15 Aug
New place to stay
Superhost
Barn in Canaan
The Cobble Barn | Fireplace • A/C • Screened Porch
2 bedrooms, 3 beds, 1 bathroom
16–21 Aug
New place to stay
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
27 Oct – 1 Nov
4.99 out of 5 average rating, 248 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
8–13 Aug
4.91 out of 5 average rating, 23 reviews
Guest favourite
Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Aug
4.89 out of 5 average rating, 158 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
9–14 Aug
4.82 out of 5 average rating, 60 reviews
Flat in Canton
New bright, spotless apartment in N. Canton
2 bedrooms, 2 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 55 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
17–22 Aug
4.88 out of 5 average rating, 159 reviews
Guest house in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
New place to stay
Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
24–29 Aug
4.87 out of 5 average rating, 15 reviews