Search results; Over 1,000 places in Winchester

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Guest favourite
Home in Winsted
Newly renovated lakefront home!
9 guests4 bedrooms7 beds2 bathrooms
12–17 Apr
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12–17 Apr
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$562 SGD per night

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Guest favourite
Flat in Winchester
Gateway to the Berkshires
Free cancellation
21–26 Apr
$179 SGD per night
4.91 out of 5 average rating, 374 reviews
Superhost
Serviced apartment in Winsted
Haven at Highland lake
Free cancellation
3–8 May
$136 SGD per night
4.87 out of 5 average rating, 94 reviews
Guest favourite
Flat in Winsted
Getaway for a weekend! Close to Ski Sundown.
1 bed
14–19 Apr
$153 SGD per night
4.92 out of 5 average rating, 78 reviews
Top guest favourite
Home in Winsted
Cheerful 2 Bedroom Home at Highland Lake
Free cancellation
1–6 May
$217 SGD per night
4.99 out of 5 average rating, 110 reviews
Guest favourite
Flat in Winsted
2nd Floor The Inn at Highland Lake
5 beds
13–18 Apr
$204 SGD per night
4.88 out of 5 average rating, 49 reviews
Home in Winsted
Renovated lake house, just steps to the water.
4 beds
12–17 Apr
$214 SGD per night
4.62 out of 5 average rating, 21 reviews
Guest favourite
Cottage in Winsted
Waterfront Cottage at Highland Lake w/dock
Free cancellation
19–24 Apr
$303 SGD per night
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Winchester
Private Suite 2 Bedroom Deck Lake Views
2 beds
19–24 Apr
$170 SGD per night
4.95 out of 5 average rating, 132 reviews
Top guest favourite
Home in Winsted
Lake House- Great for Families
7 beds
13–18 Apr
$419 SGD per night
5.0 out of 5 average rating, 50 reviews
Flat in Winsted
“Hidden Gem | Fully Private ”
2 queen beds
14–19 Apr
$203 SGD per night
4.6 out of 5 average rating, 10 reviews
Guest favourite
Tiny home in New Hartford
West Hill Outpost
Free cancellation
22–27 Apr
$176 SGD per night
4.91 out of 5 average rating, 47 reviews
Top guest favourite
Guest house in Granby
Windy Top Cottage ~ A Romantic "European" Getaway
2 beds
20–25 Apr
$216 SGD per night
4.99 out of 5 average rating, 808 reviews
Guest favourite
Home in Barkhamsted
3BR Family friendly home in Riverton paradise
Free cancellation
30 Apr – 5 May
$245 SGD per night
4.93 out of 5 average rating, 15 reviews
Flat in Winsted
Peaceful country getaway from the hectic city life
2 beds
11–16 Apr
$197 SGD per night
4.79 out of 5 average rating, 43 reviews
Top guest favourite
Home in New Hartford
Private Woodland Sanctuary—3 mins to a lake beach!
Free cancellation
23–28 May
$424 SGD per night
4.95 out of 5 average rating, 62 reviews
Guest favourite
Cabin in New Hartford
West Hill Cabin
4 beds
15–20 Apr
$372 SGD per night
4.98 out of 5 average rating, 47 reviews
Guest favourite
Room in Norfolk
Stay with Katharine
Village House Hideaway
10–15 Apr
$116 SGD per night
4.95 out of 5 average rating, 102 reviews
Cottage in Winchester
Winsted - Charming Immaculate Lakefront
8 beds
12–17 Apr
$361 SGD per night
4.97 out of 5 average rating, 62 reviews