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Search results; Over 1,000 homes in Winchester

Descriptions are based on details hosts provide
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 bed, 1 private bathroom
26–31 Jul
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4.99 out of 5 average rating, 479 reviews
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
Mid-century design, one block from downtown
4.9 out of 5 average rating, 271 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
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
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
Guest suite in Winchester
Retro studio, walkable to downtown Winchester
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Cabin in Front Royal
Hot tub with sunset mountain views
4.96 out of 5 average rating, 160 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Winchester
Farmhouse on 106 acres near Winchester
4.96 out of 5 average rating, 158 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Superhost
Cabin in Great Cacapon
Riverfront cabin with a hot tub
5.0 out of 5 average rating, 4 reviews, 2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
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
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
Cabin in Luray
Hot tub and fireplace in Shenandoah Valley
5.0 out of 5 average rating, 10 reviews, 2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
Guest favourite
Home in Winchester
Historic gem with a basketball court
4.92 out of 5 average rating, 175 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
Guest favourite
Home in Millwood
Renovated farmhouse on a flower farm
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
Top guest favourite
Cottage in Winchester
Emma's Stone Cottage
4.98 out of 5 average rating, 571 reviews, 2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
Guest favourite
Cabin in Front Royal
Secluded cabin with a hot tub and fire pit
4.95 out of 5 average rating, 307 reviews, 3 bedrooms, 3 beds, 1 bathroom
7–12 Aug
Top guest favourite
Guest house in Bluemont
10-acre Blue Ridge retreat with hot tub
4.99 out of 5 average rating, 399 reviews, 1 bedroom, 2 beds, 1 bathroom
25–30 Jul