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 Clearville
4.92 out of 5 average rating, 257 reviewsGrouseland's Vacation Cottage
Cottage in Markham
4.94 out of 5 average rating, 105 reviewsSunrise Cottage in Wine Country
Cottage in Hamilton
4.94 out of 5 average rating, 310 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Cottage in Luray
4.97 out of 5 average rating, 327 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
Cottage in Orange
4.96 out of 5 average rating, 116 reviewsOur Happy Place
Cottage in McHenry
4.97 out of 5 average rating, 113 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
Cottage in Luray
5.0 out of 5 average rating, 154 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
Cottage in Harpers Ferry
4.95 out of 5 average rating, 206 reviewsHarper's Ferry Tree House/ hot tub / nature/ trees
Pet-friendly cottage rentals
Cottage in Gerrardstown
4.84 out of 5 average rating, 282 reviewsWooded Mountain Retreat near Creek
Cottage in Maurertown
4.92 out of 5 average rating, 197 reviewsThe Cottage at Little Ridge
Cottage in Hamilton
4.85 out of 5 average rating, 304 reviewsRobins Nest
Cottage in Middleburg
4.95 out of 5 average rating, 167 reviewsWaterfront Cottage at Goose Creek
Cottage in Midland
4.97 out of 5 average rating, 132 reviewsThe Stoney Cottage Hideaway
Cottage in Bentonville
4.97 out of 5 average rating, 473 reviewsThe Cottage
Cottage in Orange
4.95 out of 5 average rating, 371 reviewsPrivate Fenced Yard for Dogs/Horses - 2BR Cottage
Cottage in Waynesboro
4.92 out of 5 average rating, 204 reviewsThe Copper Cottage - near the Appalachian Trail
Private cottage rentals
Cottage in Warrenton
4.97 out of 5 average rating, 269 reviewsThe Soper House-A Quaint & Lovely Country Getaway
Cottage in Harpers Ferry
4.99 out of 5 average rating, 104 reviewsA little piece of the country in the town
Cottage in Front Royal
4.91 out of 5 average rating, 341 reviewsMountain View with pond/cottage in front royal VA
Cottage in Bluemont
4.95 out of 5 average rating, 175 reviewsThe Cottage at Stonecroft
Cottage in Harrisonburg
4.97 out of 5 average rating, 271 reviewsThe Spring House at Willow Spring Farm
Cottage in Colonial Beach
4.93 out of 5 average rating, 194 reviewsCozy cottage 3 blocks from beach
Cottage in Dillsburg
4.96 out of 5 average rating, 179 reviewsCountry Cottage by the Redwoods.
Cottage in Waterford
4.96 out of 5 average rating, 101 reviewsWheatland Spring Farm + Brewery Cottage House
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