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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
16–21 Aug
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4.99 out of 5 average rating, 481 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 191 reviews, 1 queen bed, 1 bathroom
3–8 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
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 65 reviews, 1 bed, 1 bathroom
12–17 Oct
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 243 reviews, 1 double bed, 1.5 bathrooms
3–8 Aug
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 273 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Guest favourite
Flat in Winchester
Cameron Loft 2 Story Studio with 1.5 Bath Downtown
5.0 out of 5 average rating, 16 reviews, 1 bedroom, 1 bed, 1.5 bathrooms
1–6 Aug
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
Peaceful Family Retreat in the Heart of Winchester
5.0 out of 5 average rating, 76 reviews, 1 bedroom, 3 beds, 1 bathroom
9–14 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
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
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
25–30 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
Flat in Winchester
Historic French Modern Downtown
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
17–24 Aug
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 159 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
29 Aug – 3 Sept
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
15–22 Aug
Guest favourite
Rooms in Stephens City
Comfy 2BR | Work, Relax, Explore
5.0 out of 5 average rating, 5 reviews, 2 bedrooms, 2 beds, 1 bathroom
1–6 Aug
Superhost
Room in Shenandoah
Private Room
4.72 out of 5 average rating, 18 reviews, 1 single bed, 1.5 bathrooms
1–6 Aug
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
5.0 out of 5 average rating, 4 reviews, 1 bedroom, 2 beds, 1 bathroom
2–7 Aug