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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
Hot tub with Blue Ridge Mountain views
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 479 reviews
Top guest favourite
Room in Winchester
5 minutes from historic downtown Winchester
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
4.97 out of 5 average rating, 352 reviews
Top guest favourite
Home in Winchester
Farmhouse with views near 3 wineries
3 bedrooms, 5 beds, 2 bathrooms
15–20 Jul
4.98 out of 5 average rating, 55 reviews
Top guest favourite
Flat in Winchester
Mid-century design, one block from downtown
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Guest favourite
Flat in Winchester
Three porches and a walkable downtown
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 140 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, 245 reviews
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
1 queen bed, 1 bathroom
26–31 Jul
4.94 out of 5 average rating, 63 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
4.96 out of 5 average rating, 160 reviews
Top guest favourite
Home in Winchester
Farmhouse on 106 acres near Winchester
5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
4.96 out of 5 average rating, 158 reviews
Superhost
Cabin in Great Cacapon
New Listing! Riverfront Home w/ Hot Tub & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
16–21 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
15–20 Jul
4.95 out of 5 average rating, 39 reviews
Cabin in Winchester
Mountaintop sauna, hot tub, and views
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Millwood
Renovated farmhouse on a flower farm
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Home in Winchester
Historic District Charm On Cameron Street
3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Aug
4.92 out of 5 average rating, 175 reviews
Top guest favourite
Cottage in Winchester
Stone cottage on 15 private acres
2 bedrooms, 3 beds, 2 bathrooms
25–30 Jul
4.98 out of 5 average rating, 571 reviews
Top guest favourite
Guest house in Bluemont
Skyhorse Retreat Guest House
1 bedroom, 2 beds, 1 bathroom
25–30 Jul
4.99 out of 5 average rating, 399 reviews