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Search results; Over 1,000 homes in Winchester

Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bathroom
19–24 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, 351 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
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
19–24 Jul
4.99 out of 5 average rating, 189 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, 158 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, 140 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
4.98 out of 5 average rating, 54 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, 244 reviews
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
2 bedrooms, 2 queen beds, 1.5 bathrooms
9–14 Aug
4.94 out of 5 average rating, 52 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
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
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, 9 reviews
Guest suite in Winchester
Cozy English Basement Apt
1 bedroom, 2 double beds, 1 bathroom
20–25 Jul
4.64 out of 5 average rating, 61 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 Clear Brook
Sunrise/Sunset Views
4 bedrooms, 5 beds, 2.5 bathrooms
20–25 Jul
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Home in Martinsburg
Architectural Mountaintop Retreat | Shenandoah
4 bedrooms, 5 beds, 3 bathrooms
14–19 Jul
5.0 out of 5 average rating, 24 reviews
Top guest favourite
Home in Boyce
Cottage on the Shenandoah
3 bedrooms, 3 beds, 2 bathrooms
14–19 Jul
4.99 out of 5 average rating, 81 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
2–7 Aug
4.98 out of 5 average rating, 221 reviews