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Holiday Rentals in Winchester

Find the holiday rentals that appeal to you the most

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The best holiday rentals in Winchester

Check out our pick of great holiday rentals in Winchester

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Hillbrook Inn & Spa
Charles Town (Near Winchester)
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 42 reviews
From
US$206
1 night, 2 adults
Pet-Friendly Berryville Home Walk to Main Street!
Berryville (Near Winchester)
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 6 reviews
Modern Mountain Cottage w Hot Tub, Fire Pit, WiFi
Inwood (Near Winchester)
Scored out of 10, guest rating 8.8
Fabulous - What previous guests thought, 5 reviews
Hot Tub, Wraparound Deck, & WiFi at Chalet Cabin
Inwood (Near Winchester)
Scored out of 10, guest rating 6.4
Pleasant - What previous guests thought, 6 reviews

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