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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
1–6 Aug
,
4.97 out of 5 average rating, 222 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds
2–7 Aug
4.88 out of 5 average rating, 159 reviews
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds
9–14 Sept
New place to stay
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds
16–21 Aug
5.0 out of 5 average rating, 3 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds
1–6 Aug
4.91 out of 5 average rating, 65 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds
20–25 Sept
4.94 out of 5 average rating, 36 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds
16–21 Aug
New place to stay
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds
9–14 Aug
4.88 out of 5 average rating, 172 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 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
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
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bedroom, 1 bed
16–21 Aug
4.91 out of 5 average rating, 141 reviews
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds
8–13 Aug
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Torrington
Enjoy the NW Hills, then relax by the river…
3 bedrooms, 4 beds
10–15 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
1 queen bed
12–17 Aug
4.9 out of 5 average rating, 98 reviews
Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds
16–21 Sept
4.99 out of 5 average rating, 246 reviews
Top guest favourite
Room in Torrington
Your Work or Family Trip Home Base
1 queen bed
8–13 Aug
5.0 out of 5 average rating, 11 reviews
Home in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds
16–21 Aug
New place to stay
Guest favourite
Room in Torrington
Single guest room in a cozy one level home.
1 double bed
1–6 Aug
5.0 out of 5 average rating, 9 reviews