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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
13–18 Jul
4.99 out of 5 average rating, 473 reviews
Top guest favourite
Flat in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bathroom
11–16 Jul
4.97 out of 5 average rating, 348 reviews
Guest favourite
Home in Winchester
City Charmer minutes from Old Town
2 bedrooms, 2 beds, 1 bathroom
11–16 Aug
4.97 out of 5 average rating, 284 reviews
Top guest favourite
Home in Winchester
Skyview Farmhouse
3 bedrooms, 5 beds, 2 bathrooms
1–6 Jul
4.98 out of 5 average rating, 50 reviews
Top guest favourite
Flat in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bathroom
17–22 Jul
4.95 out of 5 average rating, 201 reviews
Guest favourite
Flat in Winchester
Cozy & Charming Downtown Apartment
1 bedroom, 1 bed, 1 bathroom
1–6 Jul
5.0 out of 5 average rating, 7 reviews
Guest favourite
Flat in Winchester
Scarborough Fair walk to downtown two story apt
3 bedrooms, 6 beds, 1 bathroom
5–10 Jul
4.9 out of 5 average rating, 138 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, 240 reviews
Top guest favourite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bathroom
5–10 Jul
4.99 out of 5 average rating, 187 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, 154 reviews
Top guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 bathrooms
1–6 Jul
4.98 out of 5 average rating, 220 reviews
Top guest favourite
Home in Martinsburg
Architectural Mountaintop Retreat | Shenandoah
4 bedrooms, 5 beds, 3 bathrooms
5–10 Jul
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Cabin in Front Royal
Shenandoah Twilight | Hot Tub + Sunset Views
2 bedrooms, 2 beds, 1 bathroom
5–10 Jul
4.96 out of 5 average rating, 156 reviews
Top guest favourite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 bathrooms
11–16 Jul
5.0 out of 5 average rating, 75 reviews
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
4.93 out of 5 average rating, 44 reviews
Top guest favourite
Room in Winchester
We Welcome You to Winchester! Best reviews!
1 double bed, 1.5 bathrooms
1–6 Jul
4.93 out of 5 average rating, 239 reviews
Cabin in Luray
NEWCabin Retreat | Hot Tub, Fireplace & Fire Pit
2 bedrooms, 2 beds, 1 bathroom
6–11 Jul
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy nature escape • Hot Tub
3 bedrooms, 3 beds, 1 bathroom
1–6 Aug
4.96 out of 5 average rating, 301 reviews