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Search results; Over 1,000 homes in Winchester

Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 private bathroom
1–6 Aug
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4.97 out of 5 average rating, 223 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
16–21 Aug
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
New place to stay, 6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4.95 out of 5 average rating, 37 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Superhost
Serviced apartment in Winsted
Haven at Highland lake
4.88 out of 5 average rating, 173 reviews, 1 bedroom, 2 beds, 1 bathroom
9–14 Aug
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5.0 out of 5 average rating, 3 reviews, 5 bedrooms, 8 beds, 3 bathrooms
16–21 Aug
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
4.91 out of 5 average rating, 65 reviews, 3 bedrooms, 5 beds, 1 bathroom
1–6 Aug
Guest favourite
Tiny home in New Hartford
West Hill Outpost
4.9 out of 5 average rating, 98 reviews, 1 bed, 1 bathroom
12–17 Aug
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
4.97 out of 5 average rating, 108 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Guest house in Winchester
Highland Lake Guest House | Private Waterfront
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
4.88 out of 5 average rating, 129 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
Guest favourite
Cottage in Winsted
Cottage Ease.
4.93 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
Guest favourite
Home in New Hartford
Modern Farmhouse
4.89 out of 5 average rating, 158 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
1–6 Aug
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4.95 out of 5 average rating, 39 reviews, 4 bedrooms, 7 beds, 2 bathrooms
31 Aug – 5 Sept
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
5.0 out of 5 average rating, 61 reviews, 3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Flat in Canton
Collinsville Overlook at LaSalle
5.0 out of 5 average rating, 52 reviews, 1 bedroom, 1 bed, 1 bathroom
3–8 Aug
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
4.93 out of 5 average rating, 150 reviews, 1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept