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
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Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub
Cottage in Markham
4.94 out of 5 average rating, 100 reviewsSunrise Cottage in Wine Country
Nov. 16 – 23
Cottage in Hamilton
4.94 out of 5 average rating, 308 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Dec. 17 – 24
Cottage in Luray
4.97 out of 5 average rating, 323 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
Mar. 7 – 14
Cottage in Madison
4.96 out of 5 average rating, 332 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Apr. 7 – 14
Cottage in Orange
4.96 out of 5 average rating, 112 reviewsOur Happy Place
Dec. 9 – 16
Cottage in McHenry
4.97 out of 5 average rating, 109 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
Sep. 11 – 18
Cottage in Confluence
4.82 out of 5 average rating, 129 reviewsYough Lake/Ohiopyle/ Stream Side Cottage/ Hot Tub
Jan. 2 – 9
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
Nov. 28 – Dec. 5
Pet-friendly cottage rentals
Cottage in Hamilton
4.86 out of 5 average rating, 301 reviewsRobins Nest
Feb. 12 – 19
Cottage in Bentonville
4.97 out of 5 average rating, 469 reviewsThe Cottage
Nov. 17 – 24
Cottage in Leesburg
4.91 out of 5 average rating, 289 reviewsThe Cottage at Forest Hills Farm
Oct. 15 – 22
Cottage in Orange
4.95 out of 5 average rating, 365 reviewsPrivate Fenced Yard for Dogs/Horses - 2BR Cottage
Oct. 16 – 23
Cottage in Crozet
4.88 out of 5 average rating, 215 reviewsA-Frame Pawpaw 2 BR Cabin, Lake, Hike & Canoe
Jan. 1 – 8
Cottage in Middleburg
4.95 out of 5 average rating, 165 reviewsWaterfront Cottage at Goose Creek
Oct. 13 – 20
Cottage in Stanardsville
4.86 out of 5 average rating, 112 reviewsChateau Merlot
Jan. 23 – 30
Cottage in Leesburg
4.89 out of 5 average rating, 314 reviewsRomantic Stone Cottage Circa 1869-75 acres to Hike
Jul. 10 – 17
Private cottage rentals
Cottage in Harrisonburg
4.97 out of 5 average rating, 268 reviewsThe Spring House at Willow Spring Farm
Jul. 18 – 25
Cottage in Front Royal
4.91 out of 5 average rating, 340 reviewsMountain View with pond/cottage in front royal VA
Nov. 11 – 18
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
Nov. 6 – 13
Cottage in Elkton
4.88 out of 5 average rating, 142 reviewsBridge House, 10 min to Shen. Nat'l. Park
Oct. 16 – 23
Cottage in Capon Bridge
4.97 out of 5 average rating, 150 reviewsThe 3R's River, Relaxation, Retreat
Oct. 14 – 21
Cottage in Ruckersville
4.91 out of 5 average rating, 267 reviewsLake Haven Cottage
Dec. 29 – Jan. 5
Cottage in Shepherdstown
4.96 out of 5 average rating, 109 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
Aug. 16 – 23
Cottage in Lovettsville
4.97 out of 5 average rating, 195 reviewsCottage Escape in Virginia Wine Country
Oct. 26 – Nov. 2
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- Monthly Rentals Winchester
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