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Search results; Over 1,000 homes in Winchester

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
Downtowner
4.97 out of 5 average rating, 351 reviews, 2 bedrooms, 3 beds, 1 bathroom
2–7 Aug
Top guest favourite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
4.99 out of 5 average rating, 479 reviews, 1 bedroom, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Home in Winchester
Skyview Farmhouse
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 5 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Flat in Winchester
Downtown FUN! Personal Mid Century 2bd Apartment!
4.9 out of 5 average rating, 271 reviews, 2 bedrooms, 2 beds, 1 bathroom
19–24 Jul
Top guest favourite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
4.98 out of 5 average rating, 244 reviews, 3 bedrooms, 4 beds, 2.5 bathrooms
1–6 Aug
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
4.9 out of 5 average rating, 140 reviews, 3 bedrooms, 6 beds, 1 bathroom
19–24 Jul
Top guest favourite
Cabin in Gerrardstown
The Nest: Modern Cabin Retreat on 5 Wooded Acres
4.98 out of 5 average rating, 202 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
3–8 Aug
Top guest favourite
Guest suite in Winchester
Retro Vibe Studio
4.94 out of 5 average rating, 63 reviews, 1 bed, 1 bathroom
26–31 Jul
Top guest favourite
Flat in Winchester
Lovely 1100 Sq. ft. 1 bedroom basement apartment
5.0 out of 5 average rating, 26 reviews, 1 bedroom, 1 bed, 1 bathroom
25–30 Jul
Top guest favourite
Home in Winchester
Aunt Tim's Farmhouse
4.96 out of 5 average rating, 158 reviews, 5 bedrooms, 6 beds, 1.5 bathrooms
26–31 Jul
Top guest favourite
Cabin in High View
Mary's Cabin
4.98 out of 5 average rating, 201 reviews, 1 bedroom, 4 beds, 1 bathroom
25–30 Oct
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
4.93 out of 5 average rating, 242 reviews, 1 double bed, 1.5 bathrooms
14–19 Jul
Top guest favourite
Home in Clear Brook
Cedar Hill Cottage- 3 mi to I-81 & Rt 11
4.94 out of 5 average rating, 52 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
9–14 Aug
Top guest favourite
Flat in Winchester
Easy like a Sunday Morning 1 BR apt great location
4.95 out of 5 average rating, 125 reviews, 1 bedroom, 1 bed, 1 bathroom
7–12 Aug
Top guest favourite
Religious building in Stephens City
The Sanctuary in the Shenandoah Valley
4.96 out of 5 average rating, 135 reviews, 3 bedrooms, 6 beds, 2 bathrooms
14–19 Jul
Top guest favourite
Tiny home in Stephens City
Farm Stay in a luxury tiny home with hot tub
5.0 out of 5 average rating, 137 reviews, 1 bedroom, 1 bed, 1 bathroom
16–21 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
16–21 Aug