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Search results; Over 1,000 homes in Winchester

Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom, 5 beds, 1 private bathroom
7–12 Sept
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4.91 out of 5 average rating, 422 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4.94 out of 5 average rating, 34 reviews, 4 bedrooms, 5 beds, 2 bathrooms
1–6 Aug
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
New place to stay, 6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
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
18–23 Jul
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
4.97 out of 5 average rating, 219 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
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
20–25 Jul
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
20–25 Jul
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
14–19 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
20–25 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
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
4.97 out of 5 average rating, 108 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
10–15 Sept
Top guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
4.99 out of 5 average rating, 115 reviews, 2 bedrooms, 4 beds, 1 bathroom
2–7 Oct
Top guest favourite
Cabin in Litchfield County
Blackberry Cottage
4.93 out of 5 average rating, 148 reviews, 1 bedroom, 3 beds, 1 bathroom
19–24 Jul
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
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
5.0 out of 5 average rating, 59 reviews, 3 bedrooms, 3 beds, 1 bathroom
25–30 Jul
Top guest favourite
Guest house in Barkhamsted
Farmington River Carriage House Pleasant Valley CT
4.91 out of 5 average rating, 119 reviews, 2 bedrooms, 3 beds, 1 bathroom
28 Jul – 2 Aug
Guest favourite
Flat in Goshen
Apartment in Norfolk, CT
4.98 out of 5 average rating, 55 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Jul
Top guest favourite
Guest house in Litchfield
The Cottage @ 228 Maple
5.0 out of 5 average rating, 37 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–25 Jul
Guest favourite
Tiny home in New Marlborough
Bedroom Forest View I Sauna I Fire-pit I Trails
4.94 out of 5 average rating, 180 reviews, 2 bedrooms, 2 beds, 1 bathroom
28 Jul – 2 Aug