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Search results; Over 1,000 homes in Winchester

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
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
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
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
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
22–27 Jun
4.98 out of 5 average rating, 50 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
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
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
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
Guest favourite
Flat in Winchester
Cozy & Charming Downtown Apartment
1 bedroom, 1 bed, 1 bathroom
19–24 Jun
5.0 out of 5 average rating, 7 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, 186 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
11–16 Jul
4.97 out of 5 average rating, 195 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
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
25–30 Jun
4.93 out of 5 average rating, 238 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
19–24 Jun
4.94 out of 5 average rating, 62 reviews
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 3 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, 154 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bathroom
21–26 Jun
5.0 out of 5 average rating, 39 reviews