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Search results; Over 1,000 homes in Winchester

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~
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
19–24 Jul
4.97 out of 5 average rating, 350 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
12–17 Jul
4.98 out of 5 average rating, 54 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, 188 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, 270 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
12–17 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, 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
12–17 Jul
4.94 out of 5 average rating, 51 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 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
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
Flat in Winchester
Old Town Loft In Highly Desirable Area Downtown
1 bedroom, 1 queen bed, 1 bathroom
11–16 Jul
4.99 out of 5 average rating, 257 reviews
Top guest favourite
Flat in Winchester
Historic French Modern Downtown
2 bedrooms, 2 beds, 1 bathroom
13–18 Jul
4.95 out of 5 average rating, 39 reviews
Guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Aug
4.95 out of 5 average rating, 555 reviews
Guest favourite
Home in Millwood
Peony Place renovated farmhouse in horse country
2 bedrooms, 2 beds, 1 bathroom
27 Jul – 1 Aug
5.0 out of 5 average rating, 7 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, 44 reviews
Guest favourite
Home in Winchester
Winchester farm
3 bedrooms, 3 beds, 2.5 bathrooms
15–20 Jul
5.0 out of 5 average rating, 12 reviews