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Search results; Over 1,000 homes in Winchester

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Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 private bathroom
5–10 Oct
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4.91 out of 5 average rating, 422 reviews
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Guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
4–9 Oct
4.9 out of 5 average rating, 49 reviews
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Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
1–6 Oct
4.95 out of 5 average rating, 40 reviews
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Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
1–6 Oct
4.91 out of 5 average rating, 68 reviews
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Top guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
3 bedrooms, 4 beds, 2 bathrooms
14–19 Oct
4.99 out of 5 average rating, 252 reviews
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Home in Winsted
Lakefront Escape on Highland
5 bedrooms, 7 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Winsted
Winsted /Winchester House wifi high speed internet
4 bedrooms, 6 beds, 2 bathrooms
1–7 Oct
4.89 out of 5 average rating, 36 reviews
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Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
3 bedrooms, 8 beds, 2 bathrooms
25–30 Oct
4.97 out of 5 average rating, 79 reviews
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Superhost
Flat in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
18–23 Oct
4.87 out of 5 average rating, 185 reviews
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Top guest favourite
Home in Winsted
Luxury Highland Lake Waterfront
7 bedrooms, 11 beds, 4 bathrooms
1–6 Oct
5.0 out of 5 average rating, 38 reviews
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Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
1–6 Oct
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Superhost
Home in Winsted
Renovated lake house, just steps to the water.
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
4.8 out of 5 average rating, 65 reviews
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Guest favourite
Home in Winsted
Serene Getaway in the Berkshires
4 bedrooms, 4 beds, 4 bathrooms
30 Oct – 4 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 bedrooms, 2 beds, 1 bathroom
4–9 Oct
4.97 out of 5 average rating, 235 reviews
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Top guest favourite
Home in Winchester
Bluebird School House
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
5.0 out of 5 average rating, 10 reviews
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Top guest favourite
Cottage in Falls Village
Retreat w 50 acre forest, waterfalls, tennis/bball
3 bedrooms, 4 beds, 1 bathroom
1–6 Oct
4.99 out of 5 average rating, 134 reviews
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Guest favourite
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
1 bedroom, 1 bathroom
28 Oct – 2 Nov
4.81 out of 5 average rating, 138 reviews
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Superhost
Cabin in Sandisfield
The Lucas Cabin-Cozy Riverfront Getaway
2 bedrooms, 4 double beds, 1 bathroom
4–9 Oct
New place to stay