Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 private bathroom
31 Aug – 5 Sept
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4.9 out of 5 average rating, 421 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 32 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
7–12 Jul
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
5–10 Jul
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
18–23 Jul
4.95 out of 5 average rating, 38 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds
11–16 Jul
4.97 out of 5 average rating, 213 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
2 bedrooms, 4 beds
31 Aug – 5 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms, 8 beds
22–27 Aug
4.97 out of 5 average rating, 75 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
1–6 Aug
4.93 out of 5 average rating, 54 reviews
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, 3 reviews
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed
1–6 Jul
5.0 out of 5 average rating, 5 reviews
Home in Torrington
Beautiful poolside oasis with large cozy home!
2 bedrooms, 4 beds
8–13 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds
8–13 Sept
5.0 out of 5 average rating, 33 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds
21–26 Jul
4.99 out of 5 average rating, 244 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds
10–16 Aug
4.89 out of 5 average rating, 35 reviews
Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds
9–14 Aug
5.0 out of 5 average rating, 6 reviews
Home in Litchfield
Charming Victorian | Walk to Litchfield Green
4 bedrooms, 4 beds
5–10 Jul
5.0 out of 5 average rating, 5 reviews
Guest favourite
Flat in Torrington
Art House 3 Beds Close to Warner Theater
2 bedrooms, 3 beds
5–10 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
1–6 Aug
4.91 out of 5 average rating, 140 reviews