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 Mount Orab
5.0 out of 5 average rating, 8 reviewsStudio 200
Sep 21 – 28
G$23,401 GYD per night
Guest favorite
Home in Sardinia
4.88 out of 5 average rating, 17 reviewsSmall Town Getaway
May 10 – 17
G$30,530 GYD per night
Guest favorite
Cottage in West Union
4.96 out of 5 average rating, 57 reviewsLucky Hooks
Feb 3 – 10
G$37,495 GYD per night
Guest favorite
Cabin in Peebles
5.0 out of 5 average rating, 48 reviewsIndian Crossing Cabin
Aug 19 – 26
G$45,415 GYD per night
Guest favorite
Cabin in West Union
5.0 out of 5 average rating, 15 reviews"Clover" 1830s Cabin on Hills Fork Farm
Jul 14 – 21
G$31,013 GYD per night
Guest favorite
Farm stay in Hillsboro
4.97 out of 5 average rating, 29 reviewsA relaxing farmhouse getaway in the country.
Feb 21 – 28
G$47,346 GYD per night
Guest favorite
Cabin in Peebles
4.97 out of 5 average rating, 88 reviewsSolstice Haven A-Frame on Private 20 Acres
Aug 20 – 27
G$38,183 GYD per night
Guest favorite
Home in Ripley
4.99 out of 5 average rating, 73 reviewsStonehurst: 3 bedroom country home
Feb 27 – Mar 6
G$30,978 GYD per night
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