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Search results; Over 1,000 homes in Winchester

Hotel in Winchester
Modern Hotel with Small Town Charm
1 bedroom, 1 bed, 1 private bath
Aug 22 – 27
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4.67 out of 5 average rating, 76 reviews
Top guest favorite
Home in Winchester
Downtown Chic Condo w/parking
1 bedroom, 1.5 baths
Aug 22 – 27
5.0 out of 5 average rating, 89 reviews
Top guest favorite
Cottage in Winchester
COZY+SEXY Private Country Escape! HOT TUB & Views~
1 bedroom, 1 queen bed, 1 bath
Sep 13 – 18
4.99 out of 5 average rating, 489 reviews
Top guest favorite
Home in Winchester
Cameron Charmer pristine w/double master suites
2 bedrooms, 2 queen beds, 2.5 baths
Aug 25 – 30
4.98 out of 5 average rating, 224 reviews
Top guest favorite
Home in Winchester
Colonial Getaway Near Old Town Historic Winchester
3 bedrooms, 4 beds, 2.5 baths
Aug 20 – 25
4.98 out of 5 average rating, 248 reviews
Top guest favorite
Apartment in Winchester
Old Town Modern Twist! Rock n’ Roll FUN w/Parking!
2 bedrooms, 2 beds, 1 bath
Sep 6 – 11
4.95 out of 5 average rating, 207 reviews
Top guest favorite
Apartment in Winchester
Downtowner
2 bedrooms, 3 beds, 1 bath
Sep 14 – 19
4.97 out of 5 average rating, 358 reviews
Top guest favorite
Room in Winchester
Winchester Private Room
1 queen bed, 1 bath
Aug 23 – 28
4.99 out of 5 average rating, 198 reviews
Top guest favorite
Home in Winchester
Aunt Tim's Farmhouse
5 bedrooms, 6 beds, 1.5 baths
Aug 29 – Sep 3
4.96 out of 5 average rating, 161 reviews
Top guest favorite
Home in Winchester
Springdale Mill Farmhouse with Spa House
4 bedrooms, 5 beds, 2.5 baths
Aug 21 – 26
4.87 out of 5 average rating, 93 reviews
Hotel room in Winchester
2 Queen | Travelodge Winchester | Cedar Creek
1 bedroom, 2 queen beds, 1 bath
Aug 20 – 25
New place to stay
Guest favorite
Home in Winchester
Dog Friendly Mountain Retreat w/ Views & Firepit
3 bedrooms, 4 beds, 1 bath
Aug 23 – 28
4.86 out of 5 average rating, 49 reviews
Superhost
Loft in Winchester
Immerse Yourself in Old Town #3 We'll Pay Parking!
1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 6
4.72 out of 5 average rating, 75 reviews
Guest favorite
Cabin in Stephens City
Chalet w/Hot Tub, Deck, Game Room & EV Charger
3 bedrooms, 3 beds, 2 baths
Sep 20 – 25
4.9 out of 5 average rating, 30 reviews
Top guest favorite
Home in Berryville
The Hill House at Stubblefield
2 bedrooms, 3 beds, 2.5 baths
Aug 20 – 25
4.98 out of 5 average rating, 80 reviews
Top guest favorite
Home in Winchester
Large Historic Stone Home in the Heart of Old Town
4 bedrooms, 4 beds, 3 baths
Aug 30 – Sep 4
5.0 out of 5 average rating, 78 reviews
Guest favorite
Cabin in Front Royal
Cozy Retreat near Shenandoah River HotTub•Wineries
3 bedrooms, 3 queen beds, 2.5 baths
Aug 23 – 28
5.0 out of 5 average rating, 6 reviews
Top guest favorite
Cabin in Front Royal
The Foxwood Cabin | Hot Tub, Screened Porch, Grill
2 bedrooms, 4 beds, 2 baths
Sep 26 – Oct 1
4.97 out of 5 average rating, 76 reviews
Top guest favorite
Cabin in Great Cacapon
Modern Black A-Frame Retreat in the Woods
2 bedrooms, 3 beds, 1 bath
Aug 23 – 28
5.0 out of 5 average rating, 49 reviews