Cottage holiday rentals in Winchester
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Winchester
Guests agree: these cottages are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for cottage rentals in Winchester
Cottage rentals with a hot tub
Cottage in Clearville
4.92 out of 5 average rating, 253 reviewsGrouseland's Vacation Cottage
16–23 Jul
Cottage in Hamilton
4.94 out of 5 average rating, 309 reviews*Cottage @ Firefly Cellars* VA Wine Country escape
5–12 Oct
Cottage in Madison
4.96 out of 5 average rating, 332 reviewsTHE PERFECT HIKING & WINERY COUNTRY RETREAT
23 Feb – 2 Mar
Cottage in Luray
4.97 out of 5 average rating, 323 reviewsHolly Tree Retreat Located In Beautiful Luray, VA.
27 Jul – 3 Aug
Cottage in Orange
4.96 out of 5 average rating, 113 reviewsOur Happy Place
3–10 Mar
Cottage in McHenry
4.97 out of 5 average rating, 110 reviewsCozy getaway w/ Theater, Hot Tub, and Scenic Views
12–19 Sep
Cottage in Fort Valley
4.93 out of 5 average rating, 125 reviewsCozy Cottage - HOT TUB | Mountain Views | Pets
22–29 Jul
Cottage in Luray
5.0 out of 5 average rating, 151 reviewsMountain Meadow Cottage w/ Hot tub & Mt Views
29 Oct – 5 Nov
Pet-friendly cottage rentals
Cottage in Bentonville
4.97 out of 5 average rating, 470 reviewsThe Cottage
22 Feb – 1 Mar
Cottage in Leesburg
4.91 out of 5 average rating, 289 reviewsThe Cottage at Forest Hills Farm
15–22 Jul
Cottage in Oakland
4.98 out of 5 average rating, 100 reviewsPet friendly-Cottage in the Woods
16–23 Nov
Cottage in Middleburg
4.95 out of 5 average rating, 165 reviewsWaterfront Cottage at Goose Creek
19–26 Oct
Cottage in Stanardsville
4.86 out of 5 average rating, 112 reviewsChateau Merlot
28 Jun – 5 Jul
Cottage in Woodbine
4.91 out of 5 average rating, 125 reviewsGate House
31 Oct – 7 Nov
Cottage in Stanardsville
4.8 out of 5 average rating, 230 reviewsCozy Cottage at White Lotus Eco Spa Retreat
10–17 Aug
Cottage in Normalville
4.93 out of 5 average rating, 445 reviewsNice and Cozy Rental
17–24 Aug
Private cottage rentals
Cottage in Lovettsville
4.97 out of 5 average rating, 195 reviewsCottage Escape in Virginia Wine Country
12–19 Jan
Cottage in Colonial Beach
4.93 out of 5 average rating, 189 reviewsCozy cottage 3 blocks from beach
17–24 Feb
Cottage in Front Royal
4.91 out of 5 average rating, 340 reviewsMountain View with pond/cottage in front royal VA
17–24 May
Cottage in Strasburg
4.98 out of 5 average rating, 106 reviewsShenandoah Riverfront - Happy Peach Cottage
7–14 Aug
Cottage in Capon Bridge
4.97 out of 5 average rating, 150 reviewsThe 3R's River, Relaxation, Retreat
1–8 Feb
Cottage in Shepherdstown
4.96 out of 5 average rating, 109 reviewsNEW * The Getaway Cottage at Rocky Marsh Farm
18–25 Aug
Cottage in Elkton
4.88 out of 5 average rating, 142 reviewsBridge House, 10 min to Shen. Nat'l. Park
2–9 Mar
Cottage in Ruckersville
4.91 out of 5 average rating, 267 reviewsLake Haven Cottage
10–17 Oct
Destinations to explore
- Baltimore Holiday rentals
- Cabins Holiday rentals
- Arlington Holiday rentals
- Charlottesville Holiday rentals
- Alexandria Holiday rentals
- Bethesda Holiday rentals
- Annapolis Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- Cottage rentals Deep Creek Lake
- Cottage rentals Virginia
- Rentals with a washing machine and dryer Winchester
- Flat rentals Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Monthly Rentals Winchester
- Family-friendly rentals Winchester
- Rentals with a patio Winchester
- Cabin rentals Winchester
- Pet-friendly rentals Winchester
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom