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
12–17 Jul
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4.89 out of 5 average rating, 168 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, 65 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, 32 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, 213 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
7–12 Jul
Home in Winchester
Thyme Out Coming Soon!
6 bedrooms, 10 beds, 2.5 bathrooms
1–6 Jul
New place to stay
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, 140 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
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
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
4.93 out of 5 average rating, 54 reviews
Guest favourite
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
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
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
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, 19 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, 58 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, 127 reviews
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds, 2 bathrooms
26–31 Jul
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
10–15 Sept
4.97 out of 5 average rating, 107 reviews