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Search results; Over 1,000 homes in Winchester

Top guest favourite
Apartment in Winchester
Historic District Downtown Winchester
1 bedroom, 1 bed, 1 private bathroom
22–27 Feb
,
4.99 out of 5 average rating, 91 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds
14–19 Sept
4.97 out of 5 average rating, 354 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed
16–21 Aug
4.99 out of 5 average rating, 484 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed
13–18 Aug
4.99 out of 5 average rating, 193 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds
3–8 Aug
4.98 out of 5 average rating, 222 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds
16–21 Aug
4.98 out of 5 average rating, 247 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds
29 Aug – 3 Sept
4.96 out of 5 average rating, 160 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds
3–8 Aug
4.87 out of 5 average rating, 92 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds
9–14 Aug
4.98 out of 5 average rating, 121 reviews
Superhost
Cabin in Front Royal
Whispering Tides River Cabin | *Skyline, Vineyards
2 bedrooms, 2 beds
10–15 Aug
New place to stay
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds
16–21 Aug
5.0 out of 5 average rating, 76 reviews
Top guest favourite
Guest suite in Clear Brook
Bluebird Bungalow
1 bedroom, 3 beds
3–8 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds
3–8 Aug
4.98 out of 5 average rating, 57 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds
6–11 Aug
5.0 out of 5 average rating, 78 reviews
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds
29 Aug – 3 Sept
4.95 out of 5 average rating, 310 reviews
Top guest favourite
Home in Martinsburg
So cozy
2 bedrooms, 2 beds
18–23 Aug
5.0 out of 5 average rating, 91 reviews
Guest favourite
Flat in Winchester
Two Bdrm. Flat w/ Patio Terrace
2 bedrooms, 2 beds
1–8 Oct
4.88 out of 5 average rating, 25 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed
3–8 Aug
5.0 out of 5 average rating, 17 reviews