Cottage vacation rentals in Winchester
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Top-rated cottage rentals in Winchester
Guests agree: these cottages 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 cottage rentals
Cottage rentals with a hot tub
Cottage in Markham
4.94 out of 5 average rating, 101 reviewsSunrise Cottage in Wine Country
Sep 18 – 25
Cottage in Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Sep 19 – 26
Cottage in Madison
4.96 out of 5 average rating, 333 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Nov 17 – 24
Cottage in Luray
4.97 out of 5 average rating, 323 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
Nov 19 – 26
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
Jan 20 – 27
Cottage in Fort Valley
4.93 out of 5 average rating, 127 reviewsCozy Cottage - HOT TUB | Mountain Views | Pets
Jun 14 – 21
Cottage in Berkeley Springs
4.95 out of 5 average rating, 383 reviewsHidden Hill - Cozy Downtown Cottage with Hot Tub!!
Sep 13 – 20
Cottage in Elkton
4.99 out of 5 average rating, 113 reviewsShenandoah River Retreat
Nov 9 – 16
Pet-friendly cottage rentals
Cottage in Hamilton
4.86 out of 5 average rating, 301 reviewsRobins Nest
Jul 9 – 16
Cottage in Middleburg
4.95 out of 5 average rating, 165 reviewsWaterfront Cottage at Goose Creek
Jul 16 – 23
Cottage in Leesburg
4.91 out of 5 average rating, 290 reviewsThe Cottage at Forest Hills Farm
Sep 25 – Oct 2
Cottage in Bentonville
4.97 out of 5 average rating, 470 reviewsThe Cottage
Sep 28 – Oct 5
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Dec 26 – Jan 2
Cottage in Stanardsville
4.86 out of 5 average rating, 112 reviewsChateau Merlot
Jun 27 – Jul 4
Cottage in Leesburg
4.9 out of 5 average rating, 316 reviewsRomantic Stone Cottage Circa 1869-75 acres to Hike
Mar 28 – Apr 4
Cottage in Middletown
4.91 out of 5 average rating, 225 reviewsCharming "Cream of the Crop" Cape ~❤️of Middletown
Feb 9 – 16
Private cottage rentals
Cottage in Capon Bridge
4.97 out of 5 average rating, 150 reviewsThe 3R's River, Relaxation, Retreat
Feb 2 – 9
Cottage in Harpers Ferry
4.93 out of 5 average rating, 502 reviewsThe Carriage House at Carrot Top Cottage
Dec 10 – 17
Cottage in Shepherdstown
4.96 out of 5 average rating, 109 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
Sep 17 – 24
Cottage in Elkton
4.88 out of 5 average rating, 142 reviewsBridge House, 10 min to Shen. Nat'l. Park
Jun 28 – Jul 5
Cottage in Marshall
4.98 out of 5 average rating, 126 reviewsRockhaven Farm Cottage
Oct 18 – 25
Cottage in Shenandoah
4.99 out of 5 average rating, 151 reviewsCharming Cottage in the Heart of Shenandoah!
Aug 25 – Sep 1
Cottage in Fairfield
4.96 out of 5 average rating, 249 reviewsThe Cottage
May 29 – Jun 5
Cottage in Waterford
4.96 out of 5 average rating, 101 reviewsWheatland Spring Farm + Brewery Cottage House
Jun 22 – 29
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- Rentals with a patio Winchester
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