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 favourite
Cabin in West Union
4.95 out of 5 average rating, 58 reviewsBear Necessities
Jan. 26 – Feb. 2
$163 CAD per night
Guest favourite
Home in West Union
4.9 out of 5 average rating, 21 reviewsTranquility Cottage
Sep. 12 – 19
$235 CAD per night
Guest favourite
Cabin in West Union
5.0 out of 5 average rating, 15 reviews"Clover" 1830s Cabin on Hills Fork Farm
May 13 – 20
$207 CAD per night
Guest favourite
Cabin in Peebles
5.0 out of 5 average rating, 48 reviewsIndian Crossing Cabin
Jan. 23 – 30
$329 CAD per night
Guest favourite
Farm stay in Hillsboro
4.97 out of 5 average rating, 29 reviewsA relaxing farmhouse getaway in the country.
Sep. 26 – Oct. 3
$310 CAD per night
Guest favourite
Home in Ripley
4.99 out of 5 average rating, 74 reviewsStonehurst: 3 bedroom country home
Jan. 27 – Feb. 3
$212 CAD per night
Guest favourite
Cabin in Peebles
4.97 out of 5 average rating, 90 reviewsSolstice Haven A-Frame on Private 20 Acres
Sep. 22 – 29
$262 CAD per night
Guest favourite
Farm stay in Piketon
5.0 out of 5 average rating, 46 reviewsBeautiful Barndominium Farm Setting. Private Porch
Dec. 12 – 19
$145 CAD per night
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