House vacation rentals in Winchester
Find and book unique houses on Airbnb
Top-rated house rentals in Winchester
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation 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, 110 reviewsMountain Retreat-Stunning Views/Pool/Hot tub
Home in Robertson
4.93 out of 5 average rating, 187 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
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
Home in Harpers Ferry
4.97 out of 5 average rating, 157 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Home in New Market
4.93 out of 5 average rating, 117 reviewsHistoric Peace and Plenty Farm: Pool House
Home in Boston
4.97 out of 5 average rating, 120 reviewsPeacefield - Blue Ridge views near Culpeper
Weekly house rentals
Home in Winchester
4.94 out of 5 average rating, 155 reviewsIndigo Blue modern open vibe on tree lined street
Home in Bolivar
4.96 out of 5 average rating, 190 reviewsNewly renovated - Walk to Harpers Ferry NP
Home in Harpers Ferry
4.94 out of 5 average rating, 526 reviewsEclectic & Romantic - Walk to Historic Downtown!
Home in Edinburg
4.99 out of 5 average rating, 340 reviewsThe Burrow ~ Our guest reviews say it all!
Home in Mount Crawford
4.96 out of 5 average rating, 156 reviewsRiver Views, HOT TUB, Firepit, WiFi, mins off I81!
Home in Berryville
4.95 out of 5 average rating, 194 reviewsRiverfront Getaway w/ Breathtaking Views!
Home in Berkeley Springs
4.98 out of 5 average rating, 286 reviewsAbby's Lookout - Raised Retreat w/Hot Tub & WiFi
Home in Berkeley Springs
4.99 out of 5 average rating, 104 reviews+ the Lodge + @ Camp Potomac Peak
Private house rentals
Home in Woodbridge
4.91 out of 5 average rating, 124 reviewsA 1 bedroom suite near the military base and mall.
Home in Stephens City
4.96 out of 5 average rating, 114 reviewsThe Sanctuary in the Shenandoah Valley
Home in Lost City
4.91 out of 5 average rating, 211 reviewsLost River Mountaintop Getaway -Stunning Views!
Home in Stanardsville
4.78 out of 5 average rating, 380 reviewsZen River Retreat
Home in Stanardsville
5.0 out of 5 average rating, 301 reviewsSister's View
Home in Leesburg
4.98 out of 5 average rating, 133 reviewsWillow’s View
Home in Baker
4.97 out of 5 average rating, 290 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Home in Franklin
4.96 out of 5 average rating, 352 reviewsThe Black Horse Farm Vacation Home
Quick stats about house rentals in Winchester
Total rentals
30 properties
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
30 properties include access to wifi
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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