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Vacation rentals in Winchester

Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness, and more.

Blueridge Mountain Retreat Apartment
SUPERHOSTEntire guest suite · 4 guests · 2 beds · 1 bath
Blueridge Mountain Retreat Apartment

In the middle of VA wine country and only minutes to the Appalachian Trail. Enjoy a private apartment in our mountain home with a separate entrance and your own deck with views of the Shenandoah Valley. There is an outbuilding with a cedar lined Swedish sauna, a hot tub on the deck, and a fire pit overlooking the valley, which is shared with our other Airbnb Guest House. Plenty of wildlife. A welcome basket includes breakfast items and a bottle of wine.

What guests are saying:

“Great stay as always; This is the first I've been here in months (since before this whole corona-virus thing started) and everything is as good as it was previously. Great relaxing location; polite and responsive hosts; everything was well-stocked including food and water and caffeine, hygiene items, various comfort items, and cleaning supplies. Everything was very clean, so no need to worry if you have concerns about hygiene in the current situation. All in all a good experience as always, it's good to know that nothing's changed for the worse even with all the mess that's happening these days.”

Private efficiency apartment
SUPERHOSTEntire apartment · 2 guests · 1 bed · 1 bath
Private efficiency apartment

This is our fifth year hosting with airbnb. Butch is a retired teacher, part time pastor & keeps busy with handyman jobs. Beth works full time taking care of Butch.

What guests are saying:

“Butch was a great host and the apartment was perfect for our weekend. It was incredibly clean and he let us know that he goes through and cleans and sanitizes himself after every guest. Butch had good knowledge of the area and was able to give us advice for hiking, shopping and fishing. The apartment itself is in a good location, close to downtown Charles Town, Harpers Ferry and Shepherdstown. We would definitely stay here again.”

Ashby's Perch -- A Very Special Retreat
SUPERHOSTEntire house · 2 guests · 1 bed · 1 bath
Ashby's Perch -- A Very Special Retreat

Sweeping views of Ashby's Gap just minutes away from Upperville and Middleburg, 1 hour outside of DC. Newly renovated with a vintage flair, private and secluded. Ideal weekend get-away for couples, come sample the best the Piedmont has to offer!

What guests are saying:

“This is a top of the line AirBnb experience. This beautiful cottage built of chestnut timbers, stone flooring in a totally inspiring location gives you a view of the mountains and peace of mind. The bedroom and kitchen are excellently appointed and every piece of furniture is beautiful. It’s location is close to wineries and lush country and not far from sweet towns with delicious restaurants. It would be lovely to return in the fall or winter:) and I highly recommend this beautiful space.”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
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Popular amenities for Winchester vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Winchester

Mountaintop Retreat
SUPERHOSTEntire chalet
Mountaintop Retreat
Price:$654 CAD/night
Circa 1792 restored log cabin
SUPERHOSTEntire cabin
Circa 1792 restored log cabin
Price:$184 CAD/night
Last Rodeo Cottage
SUPERHOSTEntire cottage
Last Rodeo Cottage
Price:$101 CAD/night
A Great Getaway — Foxglove Retreat
SUPERHOSTEntire apartment
A Great Getaway — Foxglove Retreat
Price:$343 CAD/night
Arden House, Inwood WV
SUPERHOSTEntire house
Arden House, Inwood WV
Price:$79 CAD/night
Emma's Stone Cottage
SUPERHOSTEntire cottage
Emma's Stone Cottage
Price:$135 CAD/night
We Welcome You to Winchester!
SUPERHOSTPrivate room
We Welcome You to Winchester!
Price:$81 CAD/night
Hot tub, private bedroom and bath. Huge great room
SUPERHOSTPrivate room
Hot tub, private bedroom and bath. Huge great room
Price:$73 CAD/night
The Dome at Our Farm
SUPERHOSTDome house
The Dome at Our Farm
Price:$131 CAD/night
The Farm at Clover Hill
SUPERHOSTEntire house
The Farm at Clover Hill
Price:$330 CAD/night
Wooded Mountain Retreat on Creek
SUPERHOSTEntire cottage
Wooded Mountain Retreat on Creek
Price:$139 CAD/night
Historic Rockdale Farm Private Wing
Farm stay
Historic Rockdale Farm Private Wing
Price:$103 CAD/night
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