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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

$893 SGD for 5 nights

,

4.97 out of 5 average rating, 223 reviews

Home in Winchester

Waterfront & Guest House Available in Winsted, CT!

5 bedrooms, 7 beds, 3 bathrooms

12–17 Aug

$8,654 SGD for 5 nights

New place to stay

Home in Winchester

NEW! Lakefront Retreat on Highland Lake

6 bedrooms, 10 beds, 2.5 bathrooms

9–14 Sept

$6,908 SGD for 5 nights

Free cancellation

New place to stay

Top guest favourite

Home in Winchester

Highland Lakefront Retreat

4 bedrooms, 5 beds, 2 bathrooms

20–25 Sept

$2,452 SGD for 5 nights

4.95 out of 5 average rating, 37 reviews

Home in Winchester

Spacious Lakefront Retreat w/Dock | Close to Town

5 bedrooms, 8 beds, 3 bathrooms

16–21 Aug

$8,272 SGD for 5 nights

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 bathroom

1–6 Aug

$2,585 SGD for 5 nights

4.91 out of 5 average rating, 65 reviews

Guest favourite

Villa in Winsted

Waterfront Litchfield Hills 1-bdrm Old Mill villa

1 bedroom, 1 bed, 1.5 bathrooms

1–6 Aug

$9,142 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 6 reviews

Guest favourite

Cottage in Winsted

Waterfront Cottage at Highland Lake w/dock

2 bedrooms, 4 beds, 2.5 bathrooms

31 Aug – 5 Sept

$2,584 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Superhost

Serviced apartment in Winsted

Haven at Highland lake

1 bedroom, 2 beds, 1 bathroom

18–23 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

$1,295 SGD for 5 nights

4.88 out of 5 average rating, 130 reviews

Guest house in Winchester

Highland Lake Guest House | Private Waterfront

2 bedrooms, 4 beds, 1 bathroom

12–17 Aug

$3,619 SGD for 5 nights

Free cancellation

New place to stay

Guest favourite

Home in New Hartford

Modern Farmhouse

3 bedrooms, 3 queen beds, 1.5 bathrooms

1–6 Aug

$1,242 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 158 reviews

Top guest favourite

Flat in Canton

Collinsville Overlook at LaSalle

1 bedroom, 1 queen bed, 1 bathroom

3–8 Aug

$1,448 SGD for 5 nights

5.0 out of 5 average rating, 52 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

$1,758 SGD for 5 nights

4.97 out of 5 average rating, 108 reviews

Guest favourite

Cottage in Winsted

Cottage Ease.

2 bedrooms, 2 beds, 1 bathroom

17–22 Aug

$1,524 SGD for 5 nights

4.93 out of 5 average rating, 54 reviews

Top guest favourite

Home in Torrington

Clean & Quiet Home| Enclosed 3 Season Porch & Deck

3 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$1,357 SGD for 5 nights

5.0 out of 5 average rating, 62 reviews

Top guest favourite

Room in Norfolk

Norfolk's Charming Suite in the heart of town

1 queen bed, 1 bathroom

1–6 Aug

$838 SGD for 5 nights

4.94 out of 5 average rating, 144 reviews

Top guest favourite

Cabin in Litchfield County

Blackberry Cottage

1 bedroom, 3 beds, 1 bathroom

30 Aug – 4 Sept

$1,474 SGD for 5 nights

4.93 out of 5 average rating, 150 reviews

Guest favourite

Home in Winsted

Spacious & serene house in Berkshires

4 bedrooms, 5 beds, 3.5 bathrooms

8–13 Aug

$3,043 SGD for 5 nights

4.91 out of 5 average rating, 22 reviews