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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
2–7 Aug
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4.97 out of 5 average rating, 223 reviews
Top guest favourite
Home in Winchester
Highland Lakefront Retreat
4 bedrooms, 5 beds, 2 bathrooms
20–25 Sept
4.95 out of 5 average rating, 37 reviews
Home in Winchester
Waterfront & Guest House Available in Winsted, CT!
5 bedrooms, 7 beds, 3 bathrooms
12–17 Aug
New place to stay
Home in Winchester
NEW! Lakefront Retreat on Highland Lake
6 bedrooms, 10 beds, 2.5 bathrooms
9–14 Sept
New place to stay
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
3 bedrooms, 5 beds, 1 bathroom
10–15 Aug
4.91 out of 5 average rating, 65 reviews
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
Guest favourite
Cottage in Winsted
Cottage Ease.
2 bedrooms, 2 beds, 1 bathroom
17–22 Aug
4.93 out of 5 average rating, 54 reviews
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms, 8 beds, 3 bathrooms
19–24 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Guest suite in Norfolk
The Nest at Lovers Lane
2 bedrooms, 5 beds, 1 bathroom
9–14 Aug
5.0 out of 5 average rating, 63 reviews
Guest favourite
Room in Barkhamsted
Sweet Suite in Lakefront Chalet-pvt bath
2 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 159 reviews
Top guest favourite
Home in Winsted
Newly renovated lakefront home!
4 bedrooms, 7 beds, 2 bathrooms
31 Aug – 5 Sept
4.95 out of 5 average rating, 39 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.87 out of 5 average rating, 174 reviews
Superhost
Home in Torrington
Charming Home in Litchfield County on a MAIN ROAD!
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.88 out of 5 average rating, 130 reviews
Guest favourite
Home in New Hartford
Modern Farmhouse
3 bedrooms, 3 queen beds, 1.5 bathrooms
2–7 Aug
4.89 out of 5 average rating, 158 reviews
Guest house in Winchester
Highland Lake Guest House | Private Waterfront
2 bedrooms, 4 beds, 1 bathroom
12–17 Aug
New place to stay
Top guest favourite
Flat in Canton
Collinsville Overlook at LaSalle
1 bedroom, 1 queen bed, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 53 reviews
Top guest favourite
Home in Torrington
Clean & Quiet Home| Enclosed 3 Season Porch & Deck
3 bedrooms, 3 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 63 reviews
Top guest favourite
Cabin in Harwinton
Beautiful Brook-side Log Cabin on 3 Private Acres
2 bedrooms, 2 queen beds, 1.5 bathrooms
14–19 Sept
4.97 out of 5 average rating, 108 reviews