Cottage holiday 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.
Holiday rentals for every style
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Popular amenities for Winchester cottage rentals
Cottage rentals with a hot tub
Cottage in Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
21 – 28 Nov
Cottage in Markham
4.94 out of 5 average rating, 102 reviewsSunrise Cottage in Wine Country
15 – 22 Apr
Cottage in Madison
4.96 out of 5 average rating, 333 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
6 – 13 Jan
Cottage in Luray
4.97 out of 5 average rating, 323 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
23 – 30 Nov
Cottage in Orange
4.96 out of 5 average rating, 113 reviewsOur Happy Place
16 – 23 Apr
Cottage in Confluence
4.82 out of 5 average rating, 129 reviewsYough Lake/Ohiopyle/ Stream Side Cottage/ Hot Tub
27 May – 3 June
Cottage in McHenry
4.97 out of 5 average rating, 110 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
11 – 18 Sept
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
22 – 29 Jan
Pet-friendly cottage rentals
Cottage in Leesburg
4.91 out of 5 average rating, 290 reviewsThe Cottage at Forest Hills Farm
11 – 18 Jan
Cottage in Bentonville
4.97 out of 5 average rating, 470 reviewsThe Cottage
9 – 16 Jan
Cottage in Harpers Ferry
4.94 out of 5 average rating, 244 reviewsAdorable apartment with a view
25 May – 1 June
Cottage in Crozet
4.88 out of 5 average rating, 215 reviewsA-Frame Pawpaw 2 BR Cabin, Lake, Hike & Canoe
4 – 11 Feb
Cottage in Oakland
4.98 out of 5 average rating, 100 reviewsPet friendly-Cottage in the Woods
26 Dec – 2 Jan
Cottage in Stanardsville
4.86 out of 5 average rating, 112 reviewsChateau Merlot
4 – 11 Jan
Cottage in Middleburg
4.95 out of 5 average rating, 165 reviewsWaterfront Cottage at Goose Creek
12 – 19 Oct
Cottage in Normalville
4.93 out of 5 average rating, 445 reviewsNice and Cozy Rental
11 – 18 July
Private cottage rentals
Cottage in Bluemont
4.95 out of 5 average rating, 171 reviewsThe Cottage at Stonecroft
18 – 25 Sept
Cottage in Harrisonburg
4.97 out of 5 average rating, 269 reviewsThe Spring House at Willow Spring Farm
21 – 28 July
Cottage in Capon Bridge
4.97 out of 5 average rating, 150 reviewsThe 3R's River, Relaxation, Retreat
4 – 11 Feb
Cottage in Front Royal
4.91 out of 5 average rating, 340 reviewsMountain View with pond/cottage in front royal VA
29 Dec – 5 Jan
Cottage in Strasburg
4.98 out of 5 average rating, 106 reviewsShenandoah Riverfront - Happy Peach Cottage
4 – 11 June
Cottage in Harpers Ferry
4.93 out of 5 average rating, 503 reviewsThe Carriage House at Carrot Top Cottage
31 Dec – 7 Jan
Cottage in Ruckersville
4.91 out of 5 average rating, 268 reviewsLake Haven Cottage
29 Nov – 6 Dec
Cottage in Shepherdstown
4.96 out of 5 average rating, 109 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
14 – 21 Nov
Destinations to explore
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