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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 beds, 2.5 private bathrooms
2–7 Aug
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4.98 out of 5 average rating, 221 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 479 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Room in Winchester
Winchester Private Room
4.99 out of 5 average rating, 189 reviews, 1 queen bed, 1 bathroom
19–24 Jul
Top guest favourite
Flat in Winchester
1920s home near the pedestrian mall
4.97 out of 5 average rating, 352 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Home in Winchester
Farmhouse with views near 3 wineries
4.98 out of 5 average rating, 55 reviews, 3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 271 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 201 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Guest favourite
Flat in Winchester
Three porches and a walkable downtown
4.9 out of 5 average rating, 140 reviews, 3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
4.96 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
26–31 Jul
Superhost
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
Top guest favourite
Home in Winchester
Colonial home near Old Town Winchester
4.98 out of 5 average rating, 245 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 158 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Flat in Winchester
Parisian-style flat in an 1840s home
4.95 out of 5 average rating, 39 reviews, 2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Cabin in Winchester
Mountaintop sauna, hot tub, and views
5.0 out of 5 average rating, 3 reviews, 1 bedroom, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Tiny home in Augusta
Hot tub, sauna, and Appalachian hilltop views
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 6 beds, 1 bathroom
17–22 Aug
Top guest favourite
Guest house in Bluemont
Skyhorse Retreat Guest House
4.99 out of 5 average rating, 399 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug