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Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Foxtrot Mokki | Secluded Getaway 2 Hours from DC
2 bedrooms, 2 beds, 2 private bathrooms
5–10 Oct
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4.95 out of 5 average rating, 175 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 489 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
22–27 Aug
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
25–30 Aug
4.98 out of 5 average rating, 224 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
11–16 Sept
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 161 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
23–28 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
6–11 Sept
4.95 out of 5 average rating, 207 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
22–27 Aug
4.87 out of 5 average rating, 93 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 358 reviews
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds, 1 bathroom
28 Nov – 3 Dec
4.95 out of 5 average rating, 315 reviews
Guest favourite
Cabin in Front Royal
Cozy Retreat near Shenandoah River HotTub•Wineries
3 bedrooms, 3 queen beds, 2.5 bathrooms
23–28 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
6–11 Sept
4.93 out of 5 average rating, 57 reviews
Hotel room in Winchester
2 Queen | Travelodge Winchester | Cedar Creek
1 bedroom, 2 queen beds, 1 bathroom
21–26 Aug
New place to stay
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
3–8 Oct
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
12–17 Sept
4.96 out of 5 average rating, 166 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 49 reviews