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 Lost City
5.0 out of 5 average rating, 108 reviewsMountain Retreat-Stunning Views/Pool/Hot tub
Jun 21 – 28
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Mar 5 – 12
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Feb 11 – 18
Home in Harpers Ferry
4.97 out of 5 average rating, 156 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Dec 31 – Jan 7
Home in Boston
4.97 out of 5 average rating, 118 reviewsPeacefield - Blue Ridge views near Culpeper
Oct 11 – 18
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
Mar 5 – 12
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
Sep 25 – Oct 2
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
Jan 4 – 11
Weekly house rentals
Home in Bluemont
4.92 out of 5 average rating, 204 reviewsThe Country French Cottage at High Meadows Estate
Jan 29 – Feb 5
Home in Edinburg
4.96 out of 5 average rating, 152 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
Sep 6 – 13
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Mar 26 – Apr 2
Home in Berkeley Springs
4.99 out of 5 average rating, 101 reviews+ the Lodge + @ Camp Potomac Peak
Mar 28 – Apr 4
Home in Mount Crawford
4.96 out of 5 average rating, 149 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
Dec 3 – 10
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
Jul 24 – 31
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
Jun 24 – Jul 1
Home in Artemas
4.97 out of 5 average rating, 102 reviewsRines' Country Getaway
Dec 30 – Jan 6
Private house rentals
Home in Stanardsville
5.0 out of 5 average rating, 299 reviewsSister's View
Jul 21 – 28
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
Jul 10 – 17
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
Jul 23 – 30
Home in Winchester
4.95 out of 5 average rating, 37 reviewsGet away in Winchester!
Jun 5 – 12
Home in Gerrardstown
5.0 out of 5 average rating, 6 reviewsMountain Views, Near DC, Hot Tub w Views, Trails
Jul 12 – 19
Home in Martinsburg
4.92 out of 5 average rating, 38 reviewsApple Harvest Addition
Jan 16 – 23
Home in Winchester
5.0 out of 5 average rating, 21 reviewsLarge Historic Stone Home in the Heart of Old Town
Aug 22 – 29
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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