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Search results; Over 1,000 homes in Winchester

Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 private bathrooms
26–31 Jul
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4.96 out of 5 average rating, 158 reviews
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
26–31 Jul
4.99 out of 5 average rating, 479 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
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
21–26 Jul
4.99 out of 5 average rating, 189 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
16–21 Jul
4.98 out of 5 average rating, 55 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
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
2 bedrooms, 2 queen beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 271 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
4.9 out of 5 average rating, 141 reviews
Top guest favourite
Cabin in High View
Mary's Cabin
1 bedroom, 4 beds, 1 bathroom
25–30 Oct
4.98 out of 5 average rating, 201 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
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
1 bedroom, 1 bed, 1 bathroom
28 Aug – 2 Sept
5.0 out of 5 average rating, 138 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
16–21 Jul
4.95 out of 5 average rating, 39 reviews
Guest favourite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 bathrooms
3–8 Aug
4.86 out of 5 average rating, 22 reviews
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds, 1 bathroom
7–12 Aug
4.95 out of 5 average rating, 307 reviews
Top guest favourite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bathroom
23–28 Aug
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Home in Martinsburg
So cozy
2 bedrooms, 2 beds, 1 bathroom
26–31 Jul
5.0 out of 5 average rating, 86 reviews
Top guest favourite
Home in Harpers Ferry
Gorgeous cabin on Blue Ridge
2 bedrooms, 2 queen beds, 1 bathroom
30 Nov – 5 Dec
4.97 out of 5 average rating, 121 reviews
Cabin in Winchester
Private Mountain Retreat | Sauna, Hot Tub & Views
1 bedroom, 2 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 3 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