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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
26–31 Jul
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4.97 out of 5 average rating, 219 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 35 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds
31 Jul – 5 Aug
New place to stay
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds
9–14 Sept
New place to stay
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds
20–25 Jul
4.89 out of 5 average rating, 171 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
20–25 Jul
4.95 out of 5 average rating, 39 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed
18–23 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
20–25 Jul
4.91 out of 5 average rating, 65 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
20–25 Jul
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds
16–21 Sept
4.99 out of 5 average rating, 246 reviews
Guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds
26–31 Jul
5.0 out of 5 average rating, 6 reviews
Superhost
Home in New Hartford
Sunset Pad. Lakefront for 2, private dock & SUPs.
1 bedroom, 1 king bed
27 Jul – 1 Aug
New place to stay
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
12–17 Aug
4.9 out of 5 average rating, 97 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
8–13 Aug
4.93 out of 5 average rating, 54 reviews
Flat in Canton
Modern and spotless apartment in North Canton
2 bedrooms, 2 beds
9–14 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
10–15 Sept
4.97 out of 5 average rating, 108 reviews
Top guest favourite
Guest house in Litchfield
The Cottage @ 228 Maple
3 bedrooms, 3 beds
20–25 Jul
5.0 out of 5 average rating, 37 reviews
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds
7–12 Sept
4.91 out of 5 average rating, 422 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds
25–30 Jul
5.0 out of 5 average rating, 60 reviews