House accommodation & holiday rentals in Winchester
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Top-rated house accommodation & rentals in Winchester
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester house rentals
House rentals with a pool
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
Home in Lost City
5.0 out of 5 average rating, 109 reviewsMountain Retreat-Stunning Views/Pool/Hot tub
Home in Harpers Ferry
4.97 out of 5 average rating, 156 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Home in Robertson
4.92 out of 5 average rating, 186 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Home in Boston
4.97 out of 5 average rating, 119 reviewsPeacefield - Blue Ridge views near Culpeper
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Home in Gettysburg
5.0 out of 5 average rating, 200 reviewsCivil War Farm House w/Heated (seasonal) Pool
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
Weekly house rentals
Home in Berryville
4.95 out of 5 average rating, 194 reviewsRiverfront Getaway w/ Breathtaking Views!
Home in Berkeley Springs
4.99 out of 5 average rating, 104 reviews+ the Lodge + @ Camp Potomac Peak
Home in Bluemont
4.92 out of 5 average rating, 205 reviewsThe Country French Cottage at High Meadows Estate
Home in Winchester
4.93 out of 5 average rating, 147 reviewsStone home in heart of downtown
Home in Sperryville
4.98 out of 5 average rating, 240 reviewsMountaintop Retreat
Home in Greencastle
4.97 out of 5 average rating, 198 reviewsCountry 2-Bed/2-Bath Apartment with Beautiful View
Home in Harpers Ferry
4.94 out of 5 average rating, 524 reviewsEclectic & Romantic - Walk to Historic Downtown!
Home in Artemas
4.97 out of 5 average rating, 103 reviewsRines' Country Getaway
Private house rentals
Home in Stephens City
4.96 out of 5 average rating, 114 reviewsThe Sanctuary in the Shenandoah Valley
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
Home in Berkeley Springs
4.98 out of 5 average rating, 285 reviewsAbby's Lookout - Raised Retreat w/Hot Tub & WiFi
Home in Paris
4.97 out of 5 average rating, 305 reviewsAshby's Perch -- A Very Special Retreat
Home in Stanardsville
5.0 out of 5 average rating, 300 reviewsSister's View
Home in Winchester
4.92 out of 5 average rating, 26 reviewsMisty Meadow has quite setting in the country.
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
Home in Winchester
4.96 out of 5 average rating, 89 reviewsAunt Tim's Farmhouse
Quick stats about house rentals in Winchester
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
1.6K reviews
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