filters

Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Flat in Winchester
Old Town 1920s Gas Station with Hot Tub
1 bedroom, 1 bed, 1 private bathroom
25–30 Jul
,
4.91 out of 5 average rating, 418 reviews
Top guest favourite
Room in Winchester
5 minutes from historic downtown Winchester
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 352 reviews
Top guest favourite
Cottage in Winchester
Hot tub with Blue Ridge Mountain views
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Home in Winchester
Farmhouse with views near 3 wineries
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
4.98 out of 5 average rating, 245 reviews
Top guest favourite
Cabin in Gerrardstown
Chalet-style cabin on 5 wooded acres
2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Aug
4.98 out of 5 average rating, 202 reviews
Guest favourite
Flat in Winchester
Three porches and a walkable downtown
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 140 reviews
Top guest favourite
Flat in Winchester
Spacious 1100 sq ft with private entrance
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 26 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
15–20 Jul
4.93 out of 5 average rating, 242 reviews
Top guest favourite
Cabin in High View
Copper tub and fire pit on 2 acres
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 201 reviews
Guest favourite
Home in Winchester
Historic gem with a basketball court
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Home in Clear Brook
Quiet single-level home with a fire pit
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Aug
4.94 out of 5 average rating, 53 reviews
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Superhost
Loft in Winchester
A 1700s loft on the walking mall
1 bedroom, 2 beds, 1 bathroom
15–22 Aug
4.72 out of 5 average rating, 75 reviews
Top guest favourite
Tiny home in Stephens City
Hot tub on a working homestead
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 138 reviews