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
Cottage in Petersham
4.99 out of 5 average rating, 148 reviewsCider House Cottage
8–15 Nov
$189 SGD per night
Guest favourite
Home in Chesterfield
4.97 out of 5 average rating, 226 reviewsCharming Country Home
29 Jan – 5 Feb
$238 SGD per night
Guest favourite
Flat in Brattleboro
4.96 out of 5 average rating, 281 reviewsApt in town 2 BR/2 levels in Victorian Farmhouse
25 Apr – 2 May
$198 SGD per night
Superhost
Guest house in Fitzwilliam
4.86 out of 5 average rating, 331 reviewsTranquil Guest House with Sauna
23–30 Nov
$198 SGD per night
Guest favourite
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
13–20 Mar
$191 SGD per night
Guest favourite
Cottage in Winchester
4.93 out of 5 average rating, 27 reviewsStorybook Lake Front Villa with Private Beach!
13–20 Sep
$417 SGD per night
Guest favourite
Holiday home in Winchester
5.0 out of 5 average rating, 9 reviewsLakefront Elegance with your own private beach
4–11 Oct
$305 SGD per night
Guest favourite
Tiny home in Brattleboro
4.94 out of 5 average rating, 34 reviewsSweet Vermont Tiny Home Get Away
27 Dec – 3 Jan
$115 SGD per night
Destinations to explore
- Cambridge Holiday rentals
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