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Search results; Over 1,000 homes in Winchester

Guest favourite
Loft in Winchester
Immerse yourself in Old Town Winchester (Apt #4)
1 bedroom, 3 beds, 1 bathroom
19–24 Jul
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4.73 out of 5 average rating, 724 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 476 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Jul
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 350 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 220 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
1–6 Jul
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
4.95 out of 5 average rating, 201 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 188 reviews, 1 queen bed, 1 bathroom
6–11 Jul
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
5.0 out of 5 average rating, 129 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
4.97 out of 5 average rating, 264 reviews, 1 bedroom, 2 beds, 1 bathroom
7–12 Jul
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 139 reviews, 3 bedrooms, 6 beds, 1 bathroom
12–17 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 241 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.93 out of 5 average rating, 45 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
12–17 Jul
Top guest favourite
Cabin in Front Royal
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
4.97 out of 5 average rating, 70 reviews, 2 bedrooms, 4 beds, 2 bathrooms
5–10 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 157 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Hotel room in Winchester
George Washington l Queen Bed l Historic Charm
1 bedroom, 1 bathroom
1–6 Jul
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
4.97 out of 5 average rating, 117 reviews, 2 bedrooms, 2 beds, 1 bathroom
13–18 Sept
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
New place to stay, 1 bedroom, 2 beds, 1 bathroom
5–10 Jul
Top guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
4.96 out of 5 average rating, 301 reviews, 3 bedrooms, 3 beds, 1 bathroom
7–12 Aug
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
4.92 out of 5 average rating, 174 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
6–11 Jul