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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 private bathrooms
17–22 Aug
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4.92 out of 5 average rating, 177 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
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
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
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
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
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
Top guest favourite
Room in Sharpsburg
Hidden Gem #1 - Stay with Dan and Alice.
1 bed, 1 bathroom
25–30 Aug
4.97 out of 5 average rating, 185 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
17–22 Aug
4.93 out of 5 average rating, 248 reviews
Top guest favourite
Guest house in New Market
Stay in a piece of history! Private Entire Cottage
2 beds, No bathroom
20–25 Sept
4.98 out of 5 average rating, 527 reviews
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
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
Home in Winchester
Misty Meadow has quite setting in the country.
2 bedrooms, 2 beds, 1.5 bathrooms
18–23 Aug
4.93 out of 5 average rating, 90 reviews
Guest favourite
Tiny home in Harpers Ferry
Romantic & Fun w/Amazing Overlook & Hot Tub
1 bedroom, 2 beds, 1 bathroom
26–31 Oct
4.96 out of 5 average rating, 208 reviews
Top guest favourite
Farm stay in Edinburg
Circle F Ranch Bunkhouse- Elevated Farm Stay
2 bedrooms, 2 beds, 2 bathrooms
13–18 Sept
5.0 out of 5 average rating, 20 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
26–31 Aug
4.97 out of 5 average rating, 272 reviews
Top guest favourite
Farm stay in Warrenton
Winters Retreat Farm Cottage - Entire house
1 bedroom, 3 beds, 1.5 bathrooms
25–30 Sept
4.97 out of 5 average rating, 755 reviews
Top guest favourite
Cabin in Fort Valley
Hidden in Shenandoah Valley|Pool|Pets|Fire Pit
1 bedroom, 3 beds, 2 bathrooms
28 Sept – 3 Oct
4.98 out of 5 average rating, 142 reviews