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Search results; Over 1,000 homes in Winchester

Guest favourite
Townhouse in Winchester
Modern Elegance in Historic Old Town Winchester
1 bedroom, 2 beds, 1.5 private bathrooms
13–18 Aug
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4.93 out of 5 average rating, 309 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
26–31 Jul
4.99 out of 5 average rating, 481 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
2–7 Aug
4.97 out of 5 average rating, 353 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
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
26–31 Jul
4.9 out of 5 average rating, 272 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
25–30 Aug
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
26–31 Jul
4.96 out of 5 average rating, 159 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds
26–31 Jul
4.9 out of 5 average rating, 142 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
24–29 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds
25–30 Oct
4.98 out of 5 average rating, 203 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds
3–8 Aug
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds
7–12 Aug
4.96 out of 5 average rating, 161 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds
3–8 Aug
4.87 out of 5 average rating, 23 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds
17–24 Aug
4.95 out of 5 average rating, 39 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds
15–20 Aug
4.92 out of 5 average rating, 49 reviews
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds
26–31 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
3 bedrooms, 6 beds
20–25 Jul
4.96 out of 5 average rating, 136 reviews