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 Madison
4.96 out of 5 average rating, 330 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Apr 11 – 18
Cottage in Hamilton
4.94 out of 5 average rating, 308 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Mar 30 – Apr 6
Cottage in Luray
4.97 out of 5 average rating, 322 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
Mar 7 – 14
Cottage in Orange
4.95 out of 5 average rating, 111 reviewsOur Happy Place
Sep 9 – 16
Cottage in McHenry
4.97 out of 5 average rating, 109 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
Sep 28 – Oct 5
Cottage in Berkeley Springs
4.95 out of 5 average rating, 382 reviewsHidden Hill - Cozy Downtown Cottage with Hot Tub!!
Feb 27 – Mar 6
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
May 1 – 8
Cottage in Harpers Ferry
4.95 out of 5 average rating, 206 reviewsHarper's Ferry Tree House/ hot tub / nature/ trees
Oct 10 – 17
Pet-friendly cottage rentals
Cottage in Hamilton
4.86 out of 5 average rating, 300 reviewsRobins Nest
Jul 23 – 30
Cottage in Berryville
4.98 out of 5 average rating, 115 reviewsGuest Cottage on Historic Estate & Cattle Farm
Jun 23 – 30
Cottage in Leesburg
4.91 out of 5 average rating, 289 reviewsThe Cottage at Forest Hills Farm
Jul 10 – 17
Cottage in Bentonville
4.97 out of 5 average rating, 469 reviewsThe Cottage
Mar 4 – 11
Cottage in Orange
4.95 out of 5 average rating, 365 reviewsPrivate Fenced Yard for Dogs/Horses - 2BR Cottage
Dec 31 – Jan 7
Cottage in Middleburg
4.95 out of 5 average rating, 164 reviewsWaterfront Cottage at Goose Creek
Aug 23 – 30
Cottage in Harrisonburg
4.94 out of 5 average rating, 491 reviews❤️ of downtown*Kingsize bed*Wifi*65in Smart TV*Roku
Dec 5 – 12
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Dec 20 – 27
Private cottage rentals
Cottage in Front Royal
4.91 out of 5 average rating, 340 reviewsMountain View with pond/cottage in front royal VA
Jan 6 – 13
Cottage in Elkton
4.88 out of 5 average rating, 142 reviewsBridge House, 10 min to Shen. Nat'l. Park
Feb 26 – Mar 5
Cottage in Ruckersville
4.91 out of 5 average rating, 267 reviewsLake Haven Cottage
Jul 29 – Aug 5
Cottage in Shepherdstown
4.96 out of 5 average rating, 108 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
Oct 11 – 18
Cottage in Capon Bridge
4.97 out of 5 average rating, 149 reviewsThe 3R's River, Relaxation, Retreat
Oct 11 – 18
Cottage in Fairfield
4.96 out of 5 average rating, 249 reviewsThe Cottage
Aug 7 – 14
Cottage in Marshall
4.98 out of 5 average rating, 126 reviewsRockhaven Farm Cottage
Jun 21 – 28
Cottage in Shenandoah
4.99 out of 5 average rating, 151 reviewsCharming Cottage in the Heart of Shenandoah!
Oct 7 – 14
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