Search results; Over 1,000 homes in Winchester

Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
20–25 Jun
4.95 out of 5 average rating, 200 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Jul
4.99 out of 5 average rating, 473 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
4.91 out of 5 average rating, 137 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.97 out of 5 average rating, 348 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 bathroom
20–25 Jul
4.97 out of 5 average rating, 284 reviews
Superhost
Home in Winchester
Modern Mountain House with Hot Tub & Views
3 bedrooms, 6 beds, 2 bathrooms
21–26 Jun
4.75 out of 5 average rating, 4 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, 240 reviews
Guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
2 bedrooms, 2 queen beds, 1 bathroom
5–10 Jul
4.95 out of 5 average rating, 548 reviews
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 126 reviews
Top guest favourite
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 255 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
22–27 Jun
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Home in Star Tannery
Cold Spring Cabin
2 bedrooms, 2 beds, 1.5 bathrooms
5–10 Jul
4.97 out of 5 average rating, 114 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
20–25 Jun
4.98 out of 5 average rating, 219 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
4.81 out of 5 average rating, 16 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
21–26 Jun
4.99 out of 5 average rating, 185 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Mountain Cabin w/hot tub!
3 bedrooms, 4 beds, 1 bathroom
20–25 Jun
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
1 bedroom, 1 king bed, 1 bathroom
25–30 Jul
5.0 out of 5 average rating, 25 reviews
Top guest favourite
Cabin in Strasburg
A Cabin Hideway
1 bedroom, 1 queen bed, 1 bathroom
28 Jun – 3 Jul
4.98 out of 5 average rating, 84 reviews