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
May 31 – Jun 7
Home in Brightwood
4.99 out of 5 average rating, 302 reviewsHilltop Haven Luxury lodging in Wine country
Oct 19 – 26
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
Jan 27 – Feb 3
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Feb 2 – 9
Home in Harpers Ferry
4.97 out of 5 average rating, 154 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Dec 13 – 20
Home in Boston
4.97 out of 5 average rating, 117 reviewsPeacefield - Blue Ridge views near Culpeper
Sep 18 – 25
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Jul 5 – 12
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
Oct 15 – 22
Weekly house rentals
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
Apr 7 – 14
Home in Harpers Ferry
4.94 out of 5 average rating, 520 reviewsEclectic & Romantic - Walk to Historic Downtown!
Jan 2 – 9
Home in Mount Crawford
4.96 out of 5 average rating, 147 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
Jan 3 – 10
Home in Berryville
4.95 out of 5 average rating, 190 reviewsRiverfront Getaway w/ Breathtaking Views!
Jul 18 – 25
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
Jun 13 – 20
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Apr 3 – 10
Home in Berkeley Springs
4.99 out of 5 average rating, 100 reviews+ the Lodge + @ Camp Potomac Peak
Jun 3 – 10
Home in Mount Jackson
4.97 out of 5 average rating, 379 reviewsLight Filled Mountain Retreat in the Shenandoah
Jun 24 – Jul 1
Private house rentals
Home in Greencastle
4.97 out of 5 average rating, 196 reviewsCountry 2-Bed/2-Bath Apartment with Beautiful View
Sep 16 – 23
Home in Dayton
4.99 out of 5 average rating, 191 reviewsCountry Oasis. No Cleaning Fees. Xfinity Internet.
Oct 12 – 19
Home in Winchester
4.91 out of 5 average rating, 11 reviewsCabin in Historic Old Town Winchester
Aug 5 – 12
Home in Winchester
4.92 out of 5 average rating, 25 reviewsMisty Meadow has quite setting in the country.
Jun 30 – Jul 7
Home in Winchester
4.94 out of 5 average rating, 36 reviewsGet away in Winchester!
May 30 – Jun 6
Home in Martinsburg
4.92 out of 5 average rating, 37 reviewsApple Harvest Addition
Aug 28 – Sep 4
Home in Martinsburg
4.93 out of 5 average rating, 73 reviewsElegant private home <2 miles from hospital
Jan 9 – 16
Home in Winchester
5.0 out of 5 average rating, 21 reviewsLarge Historic Stone Home in the Heart of Old Town
Oct 30 – Nov 6
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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