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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 private bathrooms
26–31 Jul
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4.96 out of 5 average rating, 158 reviews
Top guest favourite
Room in Winchester
5 minutes from historic downtown Winchester
4.99 out of 5 average rating, 189 reviews, 1 queen bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
Downtowner
4.97 out of 5 average rating, 352 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, 479 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Farmhouse with views near 3 wineries
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Guest suite in Winchester
Retro studio, walkable to downtown Winchester
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Cabin in Gerrardstown
Chalet-style cabin on 5 wooded acres
4.98 out of 5 average rating, 202 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Aug
Top guest favourite
Flat in Winchester
Mid-century design, one block from downtown
4.9 out of 5 average rating, 271 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Flat in Winchester
Three porches and a walkable downtown
4.9 out of 5 average rating, 140 reviews, 3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 201 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 242 reviews, 1 double bed, 1.5 bathrooms
15–20 Jul
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
4.96 out of 5 average rating, 135 reviews, 3 bedrooms, 6 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 53 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
9–14 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
15–22 Aug
Top guest favourite
Farm stay in Winchester
Top-Rated 1891 Farmhouse + Game Room + EV Charger
4.95 out of 5 average rating, 43 reviews, 3 bedrooms, 6 beds, 2 bathrooms
18–23 Jul
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
Top guest favourite
Tiny home in Stephens City
Hot tub on a working homestead
5.0 out of 5 average rating, 138 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 Aug