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 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
21–28 Jun
Home in New Market
4.94 out of 5 average rating, 115 reviewsHistoric Peace and Plenty Farm: Pool House
5–12 Mar
Home in Robertson
4.92 out of 5 average rating, 182 reviewsOne Of A Kind Home in VA Wine Country on 50 acres
11–18 Feb
Home in Harpers Ferry
4.97 out of 5 average rating, 156 reviewsHarpers Ferry Farmhouse, Heated Year Round Pool
31 Dec – 7 Jan
Home in Boston
4.97 out of 5 average rating, 118 reviewsPeacefield - Blue Ridge views near Culpeper
11–18 Oct
Home in Gettysburg
5.0 out of 5 average rating, 197 reviewsCivil War Farm House w/Heated (seasonal) Pool
5–12 Mar
Home in Hyndman
4.98 out of 5 average rating, 130 reviewsWills Mountain Ranch
25 Sep – 2 Oct
Home in Stanardsville
4.98 out of 5 average rating, 135 reviewsCharming Carrie's Cottage at Fairhill Farm
4–11 Jan
Weekly house rentals
Home in Bluemont
4.92 out of 5 average rating, 204 reviewsThe Country French Cottage at High Meadows Estate
29 Jan – 5 Feb
Home in Edinburg
4.96 out of 5 average rating, 152 reviewsCharming, Parkview Cottage, King bed, 1 mi to I-81
6–13 Sep
Home in Sperryville
4.97 out of 5 average rating, 239 reviewsMountaintop Retreat
26 Mar – 2 Apr
Home in Berkeley Springs
4.99 out of 5 average rating, 101 reviews+ the Lodge + @ Camp Potomac Peak
28 Mar – 4 Apr
Home in Mount Crawford
4.96 out of 5 average rating, 149 reviewsRiver Views, HOT TUB, Wi-Fi, TV; mins off I81!
3–10 Dec
Home in Mount Jackson
4.9 out of 5 average rating, 221 reviewsTreehouse in Bryce Resort, near Shenandoah Park
24–31 Jul
Home in Winchester
4.95 out of 5 average rating, 145 reviewsStone home in heart of downtown
24 Jun – 1 Jul
Home in Artemas
4.97 out of 5 average rating, 102 reviewsRines' Country Getaway
30 Dec – 6 Jan
Private house rentals
Home in Stanardsville
5.0 out of 5 average rating, 299 reviewsSister's View
21–28 Jul
Home in Baker
4.97 out of 5 average rating, 289 reviewsSecluded Hilltop Retreat: Log Cabin + Hot Tub
10–17 Jul
Home in Winchester
4.92 out of 5 average rating, 26 reviewsMisty Meadow has quite setting in the country.
13–20 Jun
Home in Winchester
4.92 out of 5 average rating, 12 reviewsCabin in Historic Old Town Winchester
23–30 Jul
Home in Winchester
4.95 out of 5 average rating, 37 reviewsGet away in Winchester!
5–12 Jun
Home in Gerrardstown
5.0 out of 5 average rating, 6 reviewsMountain Views, Near DC, Hot Tub w Views, Trails
12–19 Jul
Home in Martinsburg
4.92 out of 5 average rating, 38 reviewsApple Harvest Addition
16–23 Jan
Home in Winchester
5.0 out of 5 average rating, 21 reviewsLarge Historic Stone Home in the Heart of Old Town
22–29 Aug
Quick stats about house rentals in Winchester
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
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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