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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 beds, 2.5 private bathrooms
25–30 Aug
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4.98 out of 5 average rating, 223 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, 488 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
17–22 Aug
4.98 out of 5 average rating, 248 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, 88 reviews
Top guest favourite
Townhouse in Winchester
Brewhouse renovated row house steps from downtown
2 bedrooms, 3 beds, 2 bathrooms
17–22 Aug
4.95 out of 5 average rating, 106 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
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
23–28 Aug
4.99 out of 5 average rating, 198 reviews
Top guest favourite
Cabin in Gerrardstown
The Nest: Modern Cabin Retreat on 5 Wooded Acres
2 bedrooms, 3 beds, 1.5 bathrooms
20–25 Sept
4.98 out of 5 average rating, 206 reviews
Top guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
17–22 Aug
4.87 out of 5 average rating, 93 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, 5 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 357 reviews
Home in Strasburg
Strasburg Cottage Hideaway | Hot Tub + Sauna
2 bedrooms, 3 beds, 2 bathrooms
25–30 Aug
New place to stay
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
21–26 Aug
4.98 out of 5 average rating, 122 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 40 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 208 reviews