Holiday houses 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
Place to stay in Bernardston
4.95 out of 5 average rating, 333 reviewsStylish Private Studio w/Queen bed and Coded Locks
17–24 Mar
$249 NZD per night
Guest favourite
Apartment in Brattleboro
4.89 out of 5 average rating, 314 reviewsQuiet St in Town, gardens, terrace
1–8 Jul
$240 NZD per night
Superhost
Cabin in Brattleboro
4.89 out of 5 average rating, 441 reviewsCottage
27 Sep – 4 Oct
$250 NZD per night
Guest favourite
Apartment in Dummerston
4.93 out of 5 average rating, 366 reviews~Serene Barn Retreat~
25 Aug – 1 Sep
$205 NZD per night
Guest favourite
Apartment in Marlboro
4.94 out of 5 average rating, 223 reviewsShakespeare’s Folly Side Farm and AirBnB.
24–31 Dec
$266 NZD per night
Guest favourite
Cottage in Winchester
4.93 out of 5 average rating, 27 reviewsStorybook Lake Front Villa with Private Beach!
6–13 May
$602 NZD per night
Guest favourite
Holiday home in Winchester
5.0 out of 5 average rating, 9 reviewsLakefront Elegance with your own private beach
28 Sep – 5 Oct
$410 NZD per night
Guest favourite
Tiny home in Brattleboro
4.94 out of 5 average rating, 35 reviewsSweet Vermont Tiny Home Get Away
5–12 Dec
$159 NZD per night
Destinations to explore
- Cambridge Holiday rentals
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