House vacation rentals in Winchester
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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 Lost City
5.0 out of 5 average rating, 108 reviewsMountain Retreat-Stunning Views/Pool/Hot tub
Sep 6 – 13
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
Apr 4 – 11
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Oct 23 – 30
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Dec 5 – 12
Home in Harpers Ferry
4.97 out of 5 average rating, 155 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Apr 22 – 29
Home in Boston
4.97 out of 5 average rating, 118 reviewsPeacefield - Blue Ridge views near Culpeper
Oct 10 – 17
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
Feb 11 – 18
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
Jan 3 – 10
Weekly house rentals
Home in Bluemont
4.92 out of 5 average rating, 204 reviewsThe Country French Cottage at High Meadows Estate
Sep 5 – 12
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
Aug 16 – 23
Home in Berkeley Springs
4.99 out of 5 average rating, 101 reviews+ the Lodge + @ Camp Potomac Peak
Nov 13 – 20
Home in Harpers Ferry
4.94 out of 5 average rating, 522 reviewsEclectic & Romantic - Walk to Historic Downtown!
Jan 30 – Feb 6
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Mar 9 – 16
Home in Mount Crawford
4.96 out of 5 average rating, 148 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
Nov 11 – 18
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
Jul 23 – 30
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
Oct 8 – 15
Private house rentals
Home in Front Royal
4.96 out of 5 average rating, 134 reviewsHot tub w/ Sunset Views! Secluded mountain chalet
Sep 27 – Oct 4
Home in Culpeper
4.95 out of 5 average rating, 352 reviewsCharming Restored Farmhouse Minutes from Culpeper
Jan 17 – 24
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Oct 19 – 26
Home in Stephens City
4.96 out of 5 average rating, 114 reviewsThe Sanctuary in the Shenandoah Valley
Jun 3 – 10
Home in Winchester
4.92 out of 5 average rating, 26 reviewsMisty Meadow has quite setting in the country.
Jun 13 – 20
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
Aug 22 – 29
Home in Winchester
4.94 out of 5 average rating, 36 reviewsGet away in Winchester!
Jun 4 – 11
Home in Martinsburg
4.86 out of 5 average rating, 57 reviewsHome Comforts, a separate apt of 1500 sqft.
Feb 11 – 18
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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