Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester vacation rentals
Other great vacation rentals in Winchester
Guest favorite
Apartment in Dummerston
4.96 out of 5 average rating, 158 reviewsHeART Barn Retreat
Sep 12 – 19
$77 per night
Guest favorite
Home in Putney
4.95 out of 5 average rating, 307 reviewsCozy Train Depot in Putney Vermont
Sep 24 – Oct 1
$105 per night
Guest favorite
Apartment in Marlboro
4.94 out of 5 average rating, 221 reviewsShakespeare’s Folly Side Farm and AirBnB.
Nov 22 – 29
$127 per night
Guest favorite
Apartment in Brattleboro
4.96 out of 5 average rating, 281 reviewsApt in town 2 BR/2 levels in Victorian Farmhouse
May 23 – 30
$132 per night
Superhost
Guest suite in Montague
4.93 out of 5 average rating, 163 reviewsGreat Falls Private Suite
Jun 5 – 12
$87 per night
Guest favorite
Place to stay in Bernardston
4.95 out of 5 average rating, 332 reviewsStylish Private Studio w/Queen bed and Coded Locks
Jul 26 – Aug 2
$111 per night
Guest favorite
Cottage in Winchester
4.93 out of 5 average rating, 27 reviewsStorybook Lake Front Villa with Private Beach!
Aug 25 – Sep 1
$265 per night
Guest favorite
Vacation home in Winchester
5.0 out of 5 average rating, 9 reviewsLakefront Elegance with your own private beach
Dec 7 – 14
$196 per night
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