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Search results; Over 1,000 homes in Winchester
Over 1,000 homes in Winchester
Guest favourite
Guest favourite
Flat in Winchester
Gateway to the Berkshires
1 bedroom
,
·
5 beds
,
·
1 private bathroom
31 Aug – 5 Sept
31 Aug – 5 Sept
$823 SGD
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for 5 nights
$823 SGD for 5 nights
,
·
4.9 out of 5 average rating, 421 reviews
4.9 (421)
Top guest favourite
Guest favourite
Home in Winchester
Highland Lakefront Retreat
4.94 out of 5 average rating, 32 reviews
4.94 (32)
,
·
4 bedrooms
4 bedrooms
,
·
5 beds
5 beds
,
·
2 bathrooms
2 bathrooms
20–25 Sept
20–25 Sept
$2,554 SGD
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for 5 nights
$2,554 SGD for 5 nights
Guest favourite
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
4.91 out of 5 average rating, 65 reviews
4.91 (65)
,
·
3 bedrooms
3 bedrooms
,
·
5 beds
5 beds
,
·
1 bathroom
1 bathroom
5–10 Jul
5–10 Jul
$2,586 SGD
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for 5 nights
$2,586 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
4.97 out of 5 average rating, 213 reviews
4.97 (213)
,
·
2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
11–16 Jul
11–16 Jul
$934 SGD
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for 5 nights
$934 SGD for 5 nights
Home in Winchester
Spacious Lakefront Retreat w/Dock | Close to Town
5 bedrooms
5 bedrooms
,
·
8 beds
8 beds
,
·
3 bathrooms
3 bathrooms
7–12 Jul
7–12 Jul
$8,274 SGD
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for 5 nights
$8,274 SGD for 5 nights
Guest favourite
Guest favourite
Villa in Winsted
Waterfront Litchfield Hills 1-bdrm Old Mill villa
5.0 out of 5 average rating, 5 reviews
5.0 (5)
,
·
1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1.5 bathrooms
1.5 bathrooms
1–6 Jul
1–6 Jul
$9,143 SGD
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for 5 nights
$9,143 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Home in Winsted
Newly renovated lakefront home!
4.95 out of 5 average rating, 38 reviews
4.95 (38)
,
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4 bedrooms
4 bedrooms
,
·
7 beds
7 beds
,
·
2 bathrooms
2 bathrooms
18–23 Jul
18–23 Jul
$5,265 SGD
$3,921 SGD
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for 5 nights
Top guest favourite
Guest favourite
Home in Colebrook
Norbrook Farm ~ Rustic farmhouse w/ pond & trails
4.99 out of 5 average rating, 244 reviews
4.99 (244)
,
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3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
21–26 Jul
21–26 Jul
$2,286 SGD
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for 5 nights
$2,286 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Cottage in Winsted
Cottage Ease.
4.93 out of 5 average rating, 54 reviews
4.93 (54)
,
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2 bedrooms
2 bedrooms
,
·
2 beds
2 beds
,
·
1 bathroom
1 bathroom
1–6 Aug
1–6 Aug
$1,524 SGD
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for 5 nights
$1,524 SGD for 5 nights
Top guest favourite
Guest favourite
Tiny home in Litchfield
My Friend's Place
4.96 out of 5 average rating, 112 reviews
4.96 (112)
,
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1 bedroom
1 bedroom
,
·
1 bed
1 bed
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$787 SGD
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for 5 nights
$787 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Flat in Torrington
“The Clemons!” Central AC - 3 Beds - Main Level
4.99 out of 5 average rating, 152 reviews
4.99 (152)
,
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3 bedrooms
3 bedrooms
,
·
3 beds
3 beds
,
·
1.5 bathrooms
1.5 bathrooms
16–21 Aug
16–21 Aug
$1,418 SGD
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for 5 nights
$1,418 SGD for 5 nights
Pay $0 today
Free cancellation
Home in Torrington
Enjoy the NW Hills, then relax by the river…
5.0 out of 5 average rating, 3 reviews
5.0 (3)
,
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3 bedrooms
3 bedrooms
,
·
4 beds
4 beds
,
·
2 bathrooms
2 bathrooms
26–31 Jul
26–31 Jul
$1,610 SGD
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for 5 nights
$1,610 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Cottage in Barkhamsted
Cottage - 2 bdr - West Hill Lake w/ Private Beach
4.97 out of 5 average rating, 30 reviews
4.97 (30)
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2 bedrooms
2 bedrooms
,
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3 beds
3 beds
,
·
1 bathroom
1 bathroom
15–20 Aug
15–20 Aug
$1,791 SGD
Show price breakdown
for 5 nights
$1,791 SGD for 5 nights
Top guest favourite
Guest favourite
Guest house in Litchfield
The Cottage @ 228 Maple
5.0 out of 5 average rating, 34 reviews
5.0 (34)
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3 bedrooms
3 bedrooms
,
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3 beds
3 beds
,
·
2 bathrooms
2 bathrooms
13–18 Jul
13–18 Jul
$2,187 SGD
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for 5 nights
$2,187 SGD for 5 nights
Pay $0 today
Free cancellation
Top guest favourite
Guest favourite
Farm stay in West Simsbury
Flamig Farm Staycation
4.96 out of 5 average rating, 549 reviews
4.96 (549)
,
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2 bedrooms
2 bedrooms
,
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4 beds
4 beds
,
·
1 bathroom
1 bathroom
20–25 Sept
20–25 Sept
$1,273 SGD
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for 5 nights
$1,273 SGD for 5 nights
Pay $0 today
Free cancellation
Guest suite in Torrington
Garden Retreat in New England Near Lake & Trails
4.8 out of 5 average rating, 119 reviews
4.8 (119)
,
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1 bedroom
1 bedroom
,
·
1 bathroom
1 bathroom
16–21 Aug
16–21 Aug
$885 SGD
$762 SGD
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for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Cottage in Winchester
Winsted/Highland Lake/Direct Waterfront/Immaculate
4.97 out of 5 average rating, 75 reviews
4.97 (75)
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3 bedrooms
3 bedrooms
,
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8 beds
8 beds
,
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2 bathrooms
2 bathrooms
22–27 Aug
22–27 Aug
$2,743 SGD
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for 5 nights
$2,743 SGD for 5 nights
Top guest favourite
Guest favourite
Home in Torrington
Country living at it's finest
4.99 out of 5 average rating, 114 reviews
4.99 (114)
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2 bedrooms
2 bedrooms
,
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2 beds
2 beds
,
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1 bathroom
1 bathroom
28 Jul – 2 Aug
28 Jul – 2 Aug
$1,299 SGD
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for 5 nights
$1,299 SGD for 5 nights
Pay $0 today
Free cancellation
Guest favourite
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
5.0 out of 5 average rating, 17 reviews
5.0 (17)
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2 bedrooms
2 bedrooms
,
·
4 beds
4 beds
,
·
2.5 bathrooms
2.5 bathrooms
31 Aug – 5 Sept
31 Aug – 5 Sept
$2,585 SGD
Show price breakdown
for 5 nights
$2,585 SGD for 5 nights
Pay $0 today
Free cancellation
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