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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 private bathrooms
29 Aug – 3 Sept
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4.96 out of 5 average rating, 159 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 192 reviews, 1 queen bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 354 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 483 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 66 reviews, 1 bed, 1 bathroom
12–17 Oct
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.91 out of 5 average rating, 274 reviews, 2 bedrooms, 2 beds, 1 bathroom
2–7 Aug
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 17 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Winchester
Peaceful Family Retreat in the Heart of Winchester
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 3 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
4.98 out of 5 average rating, 221 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
2–7 Aug
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 244 reviews, 1 double bed, 1.5 bathrooms
4–9 Aug
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
5.0 out of 5 average rating, 88 reviews, 1 bedroom, 1.5 bathrooms
1–6 Aug
Top guest favourite
Flat in Stephens City
Spacious Charming Basement Apt
5.0 out of 5 average rating, 22 reviews, 1 bedroom, 1 bed, 1 bathroom
24–29 Aug
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 246 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
4.95 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
9–14 Aug
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
4.99 out of 5 average rating, 260 reviews, 1 bedroom, 1 bed, 1 bathroom
1–6 Aug
Guest favourite
Home in Berryville
The Cottage at Senseny
4.91 out of 5 average rating, 34 reviews, 3 bedrooms, 3 beds, 2 bathrooms
24–29 Aug
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
4.92 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
4.72 out of 5 average rating, 75 reviews, 1 bedroom, 2 beds, 1 bathroom
30 Aug – 6 Sept