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
11–16 Aug
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4.97 out of 5 average rating, 285 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, 476 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.97 out of 5 average rating, 349 reviews
Guest favourite
Flat in Winchester
Cozy & Charming Downtown Apartment
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
4.75 out of 5 average rating, 8 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
12–17 Jul
4.9 out of 5 average rating, 267 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Guest suite in Winchester
Full basement with private entrance. Hot tub
1 bedroom, 2 beds, 1 bathroom
7–12 Jul
4.97 out of 5 average rating, 264 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Jul
4.98 out of 5 average rating, 220 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
6–11 Jul
4.99 out of 5 average rating, 188 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
4.9 out of 5 average rating, 139 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, 241 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bathroom
20–25 Jul
5.0 out of 5 average rating, 41 reviews
Cabin in Winchester
Mountain Retreat | Sauna, Hot Tub & Views Near DC
1 bedroom, 2 beds, 1 bathroom
5–10 Jul
New place to stay
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 116 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, 155 reviews
Guest favourite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bathroom
8–13 Jul
4.86 out of 5 average rating, 49 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
1–6 Jul
4.93 out of 5 average rating, 239 reviews
Guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds, 1.5 bathrooms
12–17 Jul
4.93 out of 5 average rating, 44 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
4.83 out of 5 average rating, 18 reviews