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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 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.94 out of 5 average rating, 33 reviews
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
New place to stay
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, 39 reviews
Guest favourite
Home in Winsted
Lake House- Great for Families
5 bedrooms, 7 beds, 3.5 bathrooms
12–18 Aug
4.98 out of 5 average rating, 64 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
20–25 Jul
4.91 out of 5 average rating, 65 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
16–21 Jul
New place to stay
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
20–25 Jul
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
Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
8–13 Sept
5.0 out of 5 average rating, 33 reviews
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms, 8 beds, 2 bathrooms
7–12 Sept
4.97 out of 5 average rating, 76 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
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
8–13 Aug
4.93 out of 5 average rating, 54 reviews
Top guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
4.99 out of 5 average rating, 115 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
12–17 Jul
5.0 out of 5 average rating, 59 reviews
Guest favourite
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
20–25 Jul
4.89 out of 5 average rating, 171 reviews
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, 246 reviews
Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds, 2 bathrooms
10–16 Aug
4.89 out of 5 average rating, 35 reviews
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
2 bedrooms, 3 beds, 1 bathroom
15–20 Aug
4.97 out of 5 average rating, 30 reviews