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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 private bathrooms
25–30 Aug
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4.98 out of 5 average rating, 245 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 480 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 353 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
23–28 Jul
4.99 out of 5 average rating, 190 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
26–31 Jul
4.9 out of 5 average rating, 272 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 159 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
24–29 Jul
4.98 out of 5 average rating, 55 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
28 Jul – 2 Aug
5.0 out of 5 average rating, 16 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 203 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 161 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds, 1 bathroom
3–8 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.86 out of 5 average rating, 22 reviews
Home in Basye
Pet friendly treehouse at Bryce & Lake Laura
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
New place to stay
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds, 1 bathroom
30 Nov – 5 Dec
4.97 out of 5 average rating, 121 reviews
Top guest favourite
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 139 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.95 out of 5 average rating, 39 reviews