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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

$891 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

$2,440 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

$8,169 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

$6,888 SGD for 5 nights

New place to stay

Home in Winchester

Spacious Lakefront Retreat w/Dock | Close to Town

5 bedrooms, 8 beds, 3 bathrooms

19–24 Aug

$8,249 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Villa in Winsted

Waterfront Litchfield Hills 1-bdrm Old Mill villa

1 bedroom, 1 bed, 1.5 bathrooms

1–6 Aug

$9,115 SGD for 5 nights

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

$2,577 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Guest favourite

Flat in Winsted

2nd Floor The Inn at Highland Lake

3 bedrooms, 5 beds, 1 bathroom

10–15 Aug

$2,578 SGD for 5 nights

4.91 out of 5 average rating, 65 reviews

Guest house in Winchester

Highland Lake Guest House | Private Waterfront

2 bedrooms, 4 beds, 1 bathroom

12–17 Aug

$3,516 SGD for 5 nights

New place to stay

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

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

Guest favourite

Room in Barkhamsted

Sweet Suite in Lakefront Chalet-pvt bath

2 beds, 1 bathroom

2–7 Aug

$980 SGD for 5 nights

4.88 out of 5 average rating, 159 reviews

Guest favourite

Cottage in Winsted

Cottage Ease.

2 bedrooms, 2 beds, 1 bathroom

17–22 Aug

$1,520 SGD for 5 nights

4.93 out of 5 average rating, 54 reviews

Top guest favourite

Home in Colebrook

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

3 bedrooms, 4 beds, 2 bathrooms

16–21 Sept

$2,279 SGD for 5 nights

4.99 out of 5 average rating, 247 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

$1,753 SGD for 5 nights

4.97 out of 5 average rating, 108 reviews

Guest favourite

Cottage in Winchester

Winsted/Highland Lake/Direct Waterfront/Immaculate

3 bedrooms, 8 beds, 2 bathrooms

22–27 Oct

$1,861 SGD for 5 nights

4.97 out of 5 average rating, 76 reviews

Top guest favourite

Cabin in Colebrook

Rustic Pond Cabin: Nature, Stars & Serenity

2 bedrooms, 2 beds, 1.5 bathrooms

13–18 Oct

$2,498 SGD for 5 nights

4.94 out of 5 average rating, 127 reviews

Superhost

Home in Torrington

Charming Home in Litchfield County on a MAIN ROAD!

2 bedrooms, 3 beds, 1 bathroom

2–7 Aug

$1,292 SGD for 5 nights

4.88 out of 5 average rating, 130 reviews

Top guest favourite

Home in Torrington

Enjoy the NW Hills, then relax by the river…

3 bedrooms, 4 beds, 2 bathrooms

10–15 Aug

5.0 out of 5 average rating, 10 reviews