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Search results; Over 1,000 homes in Winchester

Guest favourite
Cabin in Winchester
Foxtrot Mokki | Secluded Getaway 2 Hours from DC
2 bedrooms, 2 beds, 2 private bathrooms
5–10 Oct
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4.95 out of 5 average rating, 177 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
16–21 Sept
4.99 out of 5 average rating, 198 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bathroom
1–8 Sept
4.72 out of 5 average rating, 75 reviews
Top guest favourite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 bathrooms
1–6 Sept
5.0 out of 5 average rating, 89 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
1–6 Sept
4.93 out of 5 average rating, 249 reviews
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 bathrooms
4–9 Sept
4.98 out of 5 average rating, 248 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
14–19 Sept
4.97 out of 5 average rating, 358 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
10–15 Oct
4.98 out of 5 average rating, 208 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.99 out of 5 average rating, 489 reviews
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
13–18 Sept
4.91 out of 5 average rating, 277 reviews
Top guest favourite
Home in Edinburg
Jay Birds Nest - Pet Friendly
3 bedrooms, 3 queen beds, 1 bathroom
13–18 Sept
4.97 out of 5 average rating, 690 reviews
Guest favourite
Tiny home in Harpers Ferry
Romantic & Fun w/Amazing Overlook & Hot Tub
1 bedroom, 2 beds, 1 bathroom
14–19 Sept
4.96 out of 5 average rating, 208 reviews
Top guest favourite
Guest house in New Market
Stay in a piece of history! Private Entire Cottage
2 beds, No bathroom
20–25 Sept
4.98 out of 5 average rating, 529 reviews
Top guest favourite
Room in Shepherdstown
Little Big Sky! A cozy bedroom in the country!
1 queen bed, 1 bathroom
1–6 Sept
4.97 out of 5 average rating, 102 reviews
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 bathrooms
6–11 Sept
4.96 out of 5 average rating, 161 reviews
Top guest favourite
Boutique hotel in Capon Bridge
Sycamore Suite ~ 1 of 5 Unique Stays at Basswood
1 bedroom, 2 beds, 1 bathroom
6–11 Sept
4.99 out of 5 average rating, 232 reviews
Top guest favourite
Flat in The Plains
Rose End
1 bedroom, 1 queen bed, 1 bathroom
13–18 Sept
4.98 out of 5 average rating, 719 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
12–17 Oct
4.94 out of 5 average rating, 66 reviews
Top guest favourite
Home in Martinsburg
1900 Newton School-house
1 bed, 1 bathroom
1–6 Sept
4.98 out of 5 average rating, 45 reviews