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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

$886 SGD for 5 nights

,

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

$2,427 SGD for 5 nights

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

$8,127 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

$6,852 SGD for 5 nights

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

$9,068 SGD for 5 nights

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

$2,565 SGD for 5 nights

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

$2,563 SGD for 5 nights

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

$1,512 SGD for 5 nights

4.93 out of 5 average rating, 54 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

$1,285 SGD for 5 nights

4.88 out of 5 average rating, 130 reviews

Guest favourite

Room in Barkhamsted

Sweet Suite in Lakefront Chalet-pvt bath

2 beds, 1 bathroom

2–7 Aug

$975 SGD for 5 nights

4.88 out of 5 average rating, 159 reviews

Guest favourite

Home in New Hartford

Modern Farmhouse

3 bedrooms, 3 queen beds, 1.5 bathrooms

1–6 Aug

$1,232 SGD for 5 nights

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

$1,436 SGD for 5 nights

5.0 out of 5 average rating, 53 reviews

Home in Winchester

Spacious Lakefront Retreat w/Dock | Close to Town

5 bedrooms, 8 beds, 3 bathrooms

19–24 Aug

$8,206 SGD for 5 nights

5.0 out of 5 average rating, 3 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

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

$1,744 SGD for 5 nights

4.97 out of 5 average rating, 108 reviews

Top guest favourite

Home in Torrington

Clean & Quiet Home| Enclosed 3 Season Porch & Deck

3 bedrooms, 3 beds, 1 bathroom

16–21 Aug

$1,346 SGD for 5 nights

5.0 out of 5 average rating, 62 reviews

Guest house in Winchester

Highland Lake Guest House | Private Waterfront

2 bedrooms, 4 beds, 1 bathroom

12–17 Aug

$3,498 SGD for 5 nights

New place to stay

Top guest favourite

Home in Torrington

Enjoy the NW Hills, then relax by the river…

3 bedrooms, 4 beds, 2 bathrooms

10–15 Aug

$1,420 SGD for 5 nights

5.0 out of 5 average rating, 10 reviews