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, 102 reviewsSunrise Cottage in Wine Country
Dec 10 – 17
Cottage in Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
Sep 15 – 22
Cottage in Madison
4.96 out of 5 average rating, 334 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
Feb 4 – 11
Cottage in Luray
4.97 out of 5 average rating, 324 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
Mar 3 – 10
Cottage in Orange
4.96 out of 5 average rating, 113 reviewsOur Happy Place
Mar 6 – 13
Cottage in Confluence
4.82 out of 5 average rating, 129 reviewsYough Lake/Ohiopyle/ Stream Side Cottage/ Hot Tub
Sep 28 – Oct 5
Cottage in McHenry
4.97 out of 5 average rating, 110 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
Sep 17 – 24
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
Dec 10 – 17
Pet-friendly cottage rentals
Cottage in Hamilton
4.86 out of 5 average rating, 302 reviewsRobins Nest
Sep 12 – 19
Cottage in Leesburg
4.91 out of 5 average rating, 290 reviewsThe Cottage at Forest Hills Farm
Nov 15 – 22
Cottage in Leesburg
4.9 out of 5 average rating, 316 reviewsRomantic Stone Cottage Circa 1869-75 acres to Hike
Feb 21 – 28
Cottage in Bentonville
4.97 out of 5 average rating, 470 reviewsThe Cottage
Sep 24 – Oct 1
Cottage in Middleburg
4.95 out of 5 average rating, 165 reviewsWaterfront Cottage at Goose Creek
Aug 23 – 30
Cottage in Oakland
4.98 out of 5 average rating, 100 reviewsPet friendly-Cottage in the Woods
Sep 24 – Oct 1
Cottage in Stanardsville
4.86 out of 5 average rating, 112 reviewsChateau Merlot
Apr 2 – 9
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
Sep 19 – 26
Private cottage rentals
Cottage in Bluemont
4.95 out of 5 average rating, 171 reviewsThe Cottage at Stonecroft
Mar 5 – 12
Cottage in Harpers Ferry
4.93 out of 5 average rating, 504 reviewsThe Carriage House at Carrot Top Cottage
Nov 7 – 14
Cottage in Harrisonburg
4.97 out of 5 average rating, 269 reviewsThe Spring House at Willow Spring Farm
Jul 31 – Aug 7
Cottage in Capon Bridge
4.97 out of 5 average rating, 150 reviewsThe 3R's River, Relaxation, Retreat
Feb 5 – 12
Cottage in Lovettsville
4.97 out of 5 average rating, 195 reviewsCottage Escape in Virginia Wine Country
Aug 18 – 25
Cottage in Shepherdstown
4.96 out of 5 average rating, 109 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
Nov 15 – 22
Cottage in Ruckersville
4.91 out of 5 average rating, 268 reviewsLake Haven Cottage
Nov 3 – 10
Cottage in Elkton
4.88 out of 5 average rating, 142 reviewsBridge House, 10 min to Shen. Nat'l. Park
Dec 1 – 8
Destinations to explore
- Baltimore Vacation rentals
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- Cottage rentals Deep Creek Lake
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- Rentals with a patio Winchester
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- Cabin rentals Winchester
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