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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
1–6 Aug
4.94 out of 5 average rating, 34 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
16–21 Jul
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 Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
18–23 Jul
4.95 out of 5 average rating, 39 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
20–25 Jul
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
4.97 out of 5 average rating, 219 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
16–21 Jul
5.0 out of 5 average rating, 6 reviews
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 171 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
20–25 Jul
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
4.99 out of 5 average rating, 246 reviews
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
4.93 out of 5 average rating, 148 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, 96 reviews
Flat in Canton
Modern and spotless apartment in North Canton
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
New place to stay
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
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
10–15 Sept
4.97 out of 5 average rating, 108 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
2 bedrooms, 3 beds, 1 bathroom
19–24 Jul
4.88 out of 5 average rating, 128 reviews
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
26–31 Jul
New place to stay
Guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
5.0 out of 5 average rating, 5 reviews