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Search results; Over 1,000 homes in Winchester

Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 private bathroom
2–7 Aug
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4.97 out of 5 average rating, 288 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
9–14 Aug
4.99 out of 5 average rating, 192 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
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 65 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, 481 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
4–9 Aug
4.93 out of 5 average rating, 244 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
1–6 Aug
4.9 out of 5 average rating, 273 reviews
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
1 bedroom, 1 double bed, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 16 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
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
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
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
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
1 bedroom, 1 bed, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 125 reviews
Top guest favourite
Flat in Stephens City
Spacious Charming Basement Apt
1 bedroom, 1 bed, 1 bathroom
24–29 Aug
5.0 out of 5 average rating, 22 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, 159 reviews
Superhost
Cabin in Front Royal
Whispering Tides River Cabin | *Skyline, Vineyards
2 bedrooms, 2 beds, 1 bathroom
10–15 Aug
New place to stay
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
15–22 Aug
4.72 out of 5 average rating, 75 reviews
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed, 1 bathroom
1–6 Aug
4.99 out of 5 average rating, 259 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews