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
May 31 – Jun. 7
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
Jan. 28 – Feb. 4
Home in Harpers Ferry
4.97 out of 5 average rating, 154 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
Mar. 9 – 16
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
Feb. 20 – 27
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
Oct. 21 – 28
Home in Boston
4.97 out of 5 average rating, 117 reviewsPeacefield - Blue Ridge views near Culpeper
May 31 – Jun. 7
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
Nov. 17 – 24
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
Dec. 2 – 9
Weekly house rentals
Home in Baker
4.95 out of 5 average rating, 290 reviewsLittle House on the Prairie in Baker WV
Jan. 5 – 12
Home in Edinburg
4.96 out of 5 average rating, 149 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
Sep. 11 – 18
Home in Harpers Ferry
4.94 out of 5 average rating, 521 reviewsEclectic & Romantic - Walk to Historic Downtown!
Mar. 31 – Apr. 7
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
Apr. 3 – 10
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
Mar. 31 – Apr. 7
Home in Mount Crawford
4.96 out of 5 average rating, 147 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
Jan. 2 – 9
Home in Berkeley Springs
4.99 out of 5 average rating, 100 reviews+ the Lodge + @ Camp Potomac Peak
Dec. 6 – 13
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
Jun. 9 – 16
Private house rentals
Home in Stanardsville
5.0 out of 5 average rating, 299 reviewsSister's View
Jul. 7 – 14
Home in Greencastle
4.97 out of 5 average rating, 196 reviewsCountry 2-Bed/2-Bath Apartment with Beautiful View
Nov. 8 – 15
Home in Winchester
4.91 out of 5 average rating, 11 reviewsCabin in Historic Old Town Winchester
Jul. 21 – 28
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!
Jun. 1 – 8
Home in Gerrardstown
5.0 out of 5 average rating, 5 reviewsMountain Views, Near DC, Hot Tub w Views, Trails
Jul. 19 – 26
Home in Middletown
4.95 out of 5 average rating, 43 reviewsCozy Retreat in Reliance with beautiful views
Jul. 23 – 30
Home in Martinsburg
4.93 out of 5 average rating, 74 reviewsElegant private home <2 miles from hospital
Dec. 30 – Jan. 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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