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Search results; Over 1,000 homes in Winchester

Flat in Winchester
Nostalgia Lane 3 BR in the heart of the city
3 bedrooms, 3 beds, 1 private bathroom
12–17 Aug
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4.85 out of 5 average rating, 238 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
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, 1 bathroom
16–21 Aug
4.99 out of 5 average rating, 484 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.91 out of 5 average rating, 275 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
13–18 Aug
4.99 out of 5 average rating, 192 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
1–6 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
4–9 Sept
4.98 out of 5 average rating, 246 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, 160 reviews
Guest favourite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 bathrooms
1–6 Aug
4.87 out of 5 average rating, 91 reviews
Top guest favourite
Cottage in Berryville
Milton Valley Cottage on Historic Estate Farm
2 bedrooms, 2 beds, 1.5 bathrooms
4–9 Aug
4.98 out of 5 average rating, 120 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
3–8 Aug
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Home in Winchester
Swim, kayak, fish, and enjoy nature on Back Creek
3 bedrooms, 3 beds, 3 bathrooms
15–20 Aug
4.92 out of 5 average rating, 52 reviews
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
1 bedroom, 3 beds, 1 bathroom
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, 1 bathroom
3–8 Aug
4.97 out of 5 average rating, 73 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 206 reviews
Top guest favourite
Cabin in Front Royal
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
2 bedrooms, 4 beds, 2 bathrooms
15–20 Aug
4.97 out of 5 average rating, 74 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
17–22 Aug
5.0 out of 5 average rating, 28 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
7–12 Aug
4.96 out of 5 average rating, 163 reviews