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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 private bathroom
21–26 Aug
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4.97 out of 5 average rating, 287 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 480 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 190 reviews, 1 queen bed, 1 bathroom
23–28 Jul
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 353 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 272 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
25–30 Aug
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 142 reviews, 3 bedrooms, 6 beds, 1 bathroom
26–31 Jul
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 203 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
4.95 out of 5 average rating, 308 reviews, 3 bedrooms, 3 beds, 1 bathroom
23–28 Aug
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
4.87 out of 5 average rating, 23 reviews, 3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
Home in Basye
Pet friendly treehouse at Bryce & Lake Laura
New place to stay, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
4.96 out of 5 average rating, 161 reviews, 2 bedrooms, 2 beds, 1 bathroom
7–12 Aug
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
20–25 Jul
Top guest favourite
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
5.0 out of 5 average rating, 6 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
4.97 out of 5 average rating, 121 reviews, 2 bedrooms, 2 beds, 1 bathroom
30 Nov – 5 Dec