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Search results; Over 1,000 homes in Winsted, Winchester

Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 private bathroom
5–10 Jul
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4.89 out of 5 average rating, 167 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
5–10 Jul
4.91 out of 5 average rating, 64 reviews
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, 31 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
11–16 Jul
4.97 out of 5 average rating, 211 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
4.93 out of 5 average rating, 54 reviews
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, 38 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
7–12 Jul
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed, 1 bathroom
1–6 Aug
4.91 out of 5 average rating, 139 reviews
Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
4.81 out of 5 average rating, 59 reviews
Guest favourite
Home in Winsted
Spacious & serene house in Berkshires
4 bedrooms, 5 beds, 3.5 bathrooms
28 Jul – 2 Aug
4.89 out of 5 average rating, 18 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
Tiny home in New Hartford
West Hill Outpost
1 queen bed, 1 bathroom
7–12 Jul
4.89 out of 5 average rating, 94 reviews
Home in Winchester
Lakefront Retreat on Highland Lake in Winsted
3 bedrooms, 6 beds, 2 bathrooms
7–12 Jul
New place to stay
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, 243 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
5–10 Jul
5.0 out of 5 average rating, 57 reviews
Home in Winchester
Bluebird School House
1 bedroom, 1 double bed, 1 bathroom
12–17 Jul
New place to stay
Top guest favourite
Home in Barkhamsted
2BR Family friendly home in Riverton paradise
2 bedrooms, 2 beds, 2 bathrooms
7–12 Aug
4.94 out of 5 average rating, 49 reviews
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Jul
5.0 out of 5 average rating, 5 reviews
Flat in Torrington
Charming Private Apartment Near Downtown
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Jul
New place to stay