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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
4.94 out of 5 average rating, 36 reviews, 4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
4.88 out of 5 average rating, 159 reviews, 2 beds, 1 bathroom
22–27 Jul
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
4.91 out of 5 average rating, 65 reviews, 3 bedrooms, 5 beds, 1 bathroom
21–26 Jul
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
4.89 out of 5 average rating, 171 reviews, 1 bedroom, 2 beds, 1 bathroom
26–31 Jul
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
New place to stay, 6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
4.91 out of 5 average rating, 141 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Guest favourite
Cottage in Winsted
Cottage Ease.
4.93 out of 5 average rating, 54 reviews, 2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
Top guest favourite
Room in Norfolk
Norfolk's Charming Suite in the heart of town
4.94 out of 5 average rating, 144 reviews, 1 queen bed, 1 bathroom
26–31 Jul
Room in New Hartford
Private Room in Mid-Century Modern Artist House
New place to stay, 1 queen bed, 1 bathroom
21–26 Jul
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
4.99 out of 5 average rating, 246 reviews, 3 bedrooms, 4 beds, 2 bathrooms
16–21 Sept
Guest favourite
Flat in Torrington
Modern/Private Five ★ /Hotel quality stay/1 BR Apt
4.95 out of 5 average rating, 282 reviews, 1 bedroom, 1 bed, 1 bathroom
23–28 Aug
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
5.0 out of 5 average rating, 17 reviews, 2 bedrooms, 4 beds, 2.5 bathrooms
31 Aug – 5 Sept
Top guest favourite
Flat in Canton
Charming Main Street Studio in Collinsville!
5.0 out of 5 average rating, 63 reviews, 1 bathroom
29 Jul – 3 Aug
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4.95 out of 5 average rating, 39 reviews, 4 bedrooms, 7 beds, 2 bathrooms
15–20 Sept
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
New place to stay, 5 bedrooms, 7 beds, 3 bathrooms
31 Jul – 5 Aug
Guest favourite
Home in Winsted
Lake House- Great for Families
4.98 out of 5 average rating, 64 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
19–25 Aug
Guest favourite
Tiny home in New Hartford
West Hill Outpost
4.9 out of 5 average rating, 98 reviews, 1 bed, 1 bathroom
12–17 Aug