Holiday rentals in Winchester
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Top-rated holiday rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester holiday rentals
Other great holiday rentals in Winchester
Guest favourite
Guest suite in Goshen
4.95 out of 5 average rating, 141 reviewsBirchwood Hide-Away
14–21 May
€ 163 per night
Guest favourite
Flat in Copake Falls
4.93 out of 5 average rating, 260 reviewsModern Copake Falls Getaway - 8 Mins to Catamount
11–18 Oct
€ 118 per night
Guest favourite
Flat in Brookfield
4.94 out of 5 average rating, 186 reviewsPeaceful apartment on 3.5 acres w/ Artist studio.
13–20 Jan
€ 128 per night
Guest favourite
Guest suite in Winchester
4.95 out of 5 average rating, 57 reviewsPrivate Suite 2 Bedroom Deck Lake Views
29 Sep – 6 Oct
€ 129 per night
Superhost
Flat in Winsted
4.87 out of 5 average rating, 30 reviews1st Floor The Inn at Highland Lake
6–13 Nov
€ 136 per night
Guest favourite
Flat in Winsted
4.94 out of 5 average rating, 36 reviewsGetaway for a weekend! Close to Ski Sundown.
6–13 Feb
€ 126 per night
Guest favourite
Home in Winsted
4.89 out of 5 average rating, 9 reviewsNewly renovated lakefront home!
24–31 Oct
€ 396 per night
Guest favourite
Guest house in Sharon
5.0 out of 5 average rating, 65 reviewsCottage with a Waterfall View
15–22 Sep
€ 126 per night
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