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Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 private bathroom
7–12 Sept
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4.91 out of 5 average rating, 422 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.93 out of 5 average rating, 41 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
13–18 Aug
New place to stay
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 177 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.97 out of 5 average rating, 226 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
23–28 Aug
4.93 out of 5 average rating, 153 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
24–29 Aug
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Goshen
Sun-Soaked Chalet Near Lake and Ski Mountain
4 bedrooms, 7 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 69 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 66 reviews
Guest favourite
Cabin in Colebrook
Rustic Pond Cabin: Nature, Stars & Serenity
2 bedrooms, 2 beds, 1.5 bathrooms
15–20 Sept
4.95 out of 5 average rating, 128 reviews
Guest favourite
Cottage in New Hartford
Cozy West Hill Lake Cottage Retreat
1 bedroom, 2 double beds, 1 bathroom
24–29 Aug
4.88 out of 5 average rating, 16 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 131 reviews
Top guest favourite
Farm stay in West Simsbury
Flamig Farm Staycation
2 bedrooms, 4 beds, 1 bathroom
20–25 Sept
4.96 out of 5 average rating, 555 reviews
Top guest favourite
Room in Norfolk
Maple House, Birch Room
1 queen bed, 1 bathroom
13–18 Aug
4.98 out of 5 average rating, 56 reviews
Guest house in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds, 1 bathroom
13–18 Aug
New place to stay
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
13–18 Aug
5.0 out of 5 average rating, 6 reviews
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
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
29 Aug – 3 Sept
4.93 out of 5 average rating, 57 reviews
Top guest favourite
Flat in Canton
Collinsville Overlook at LaSalle
1 bedroom, 1 queen bed, 1 bathroom
13–18 Aug
5.0 out of 5 average rating, 55 reviews