House holiday 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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Winchester
House rentals with a pool
Home in Lost City
5.0 out of 5 average rating, 108 reviewsMountain Retreat-Stunning Views/Pool/Hot tub
6–13 Sep
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
31 Jan – 7 Feb
Home in Harpers Ferry
4.97 out of 5 average rating, 155 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
25 Apr – 2 May
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
20–27 Feb
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
2–9 Mar
Home in Boston
4.97 out of 5 average rating, 118 reviewsPeacefield - Blue Ridge views near Culpeper
31 May – 7 Jun
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
26 Apr – 3 May
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
1–8 Jan
Weekly house rentals
Home in Berryville
4.95 out of 5 average rating, 190 reviewsRiverfront Getaway w/ Breathtaking Views!
18–25 Jul
Home in Myersville
4.97 out of 5 average rating, 148 reviewsThe Crooked Cottage: a Cozy, Curated Escape
4–11 Sep
Home in Mount Crawford
4.96 out of 5 average rating, 147 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
31 Oct – 7 Nov
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
30 Jan – 6 Feb
Home in Harpers Ferry
4.94 out of 5 average rating, 521 reviewsEclectic & Romantic - Walk to Historic Downtown!
9–16 Nov
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
21–28 Jul
Home in Berkeley Springs
4.99 out of 5 average rating, 101 reviews+ the Lodge + @ Camp Potomac Peak
3–10 Jun
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
29 Sep – 6 Oct
Private house rentals
Home in Stanardsville
5.0 out of 5 average rating, 299 reviewsSister's View
7–14 Jul
Home in Winchester
4.91 out of 5 average rating, 11 reviewsCabin in Historic Old Town Winchester
21–28 Jul
Home in Winchester
4.92 out of 5 average rating, 25 reviewsMisty Meadow has quite setting in the country.
28 Jun – 5 Jul
Home in Winchester
4.94 out of 5 average rating, 36 reviewsGet away in Winchester!
22–29 Nov
Home in Gerrardstown
5.0 out of 5 average rating, 5 reviewsMountain Views, Near DC, Hot Tub w Views, Trails
16–23 Jul
Home in Martinsburg
4.92 out of 5 average rating, 37 reviewsApple Harvest Addition
7–14 Jun
Home in Martinsburg
4.93 out of 5 average rating, 74 reviewsElegant private home <2 miles from hospital
30 Dec – 6 Jan
Home in Winchester
5.0 out of 5 average rating, 21 reviewsLarge Historic Stone Home in the Heart of Old Town
21–28 Aug
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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