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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, 219 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
1–6 Aug
New place to stay
Home in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
New place to stay
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
New place to stay
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 36 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 65 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
3–8 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
7–12 Aug
4.89 out of 5 average rating, 171 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
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed, 1 bathroom
12–17 Aug
4.9 out of 5 average rating, 98 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
15–20 Sept
4.95 out of 5 average rating, 39 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.93 out of 5 average rating, 54 reviews
Guest favourite
Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
1–6 Aug
4.89 out of 5 average rating, 157 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.93 out of 5 average rating, 150 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 128 reviews
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
1 bedroom, 1 king bed, 1 bathroom
1–6 Aug
New place to stay
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Room in Norfolk
Norfolk's Charming Suite in the heart of town
1 queen bed, 1 bathroom
1–6 Aug
4.94 out of 5 average rating, 144 reviews