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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.

  • Immerse yourself in Old Town Winchester
    Entire loft · 4 guests · 1 bed · 1 bath
    Immerse yourself in Old Town Winchester

    Our loft apartment is in the heart of Old Town Winchester on the Old Town Mall. Located off of a little alley, with security lighting and motion detectors you will be staying steps away from dining, shops and everything our community has to offer. Yet, our apartments are quiet and secure. Our building is OLD & has all of the charm that goes along with it. If you are looking for a sparkly new place, you may want to stay elsewhere, If you want clean, funky and awesome, we are your place!

    What guests are saying:

    “Charlie's cozy airbnb is a gem! The location could not have been better. It's right in downtown proper. We saw a show at The Bright Box and were just a short block away. She has a great selection of books and movies and the bed was comfy! I can't wait to stay here again!”

  • Lux Downtown Home
    SUPERHOSTEntire house · 6 guests · 3 beds · 1.5 baths
    Lux Downtown Home

    Come enjoy Old Town Mall in this fabulously furnished home ready for your getaway and local enjoyment. My place is a minute walk of 4 breweries, 30 restaurants, bars and over 60 retail shops. There are also numerous museums & art studios. My place is perfect for business travelers, couples, family and solo adventurers. My home is 5 minutes drive to Winchester Medical Center, and 3 to 4 minutes drive to Shenandoah University's main campus.

    What guests are saying:

    “The house was amazing. Immaculately clean, quick response, and quirky little touches. She definitely made sure the house was ready for us and quick response and for letting us know we could book it since it was a last-minute booking. She kept contact with us to make sure that we had everything we needed I definitely recommend this house if you’re looking for a quiet getaway.”

  • The Millwood House
    Entire house · 6 guests · 3 beds · 2 baths
    The Millwood House

    Nice older single family home all to yourselves. If you don’t like old houses this is not the place for you, it was built in 1955. It is close to 81 and roughly a mile from Old Town Winchester. It is located across the street from Shenandoah University. Starbucks and restaurants are a short walk. This house is perfect for families or a group of friends. Great for a weekend getaway or visiting professionals. Stop for a quick overnight while traveling. Cable TV and Wifi included.

    What guests are saying:

    “Cute house and a nice stay, everything was clean and the hosts were extremely helpful. I ran into a minor issue and they fixed it within minutes. Great hospitality and definitely worth the value”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Winchester vacation rentals

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

Other great vacation rentals in Winchester

Downtowner
SUPERHOSTEntire apartment
Downtowner
Price:€102 / night
The Comfortable In-Towner
SUPERHOSTEntire apartment
The Comfortable In-Towner
Price:€58 / night
City Charmer minutes from Old Town
SUPERHOSTEntire house
City Charmer minutes from Old Town
Price:€88 / night
Pretty Little Apt by the Train I
SUPERHOSTEntire apartment
Pretty Little Apt by the Train I
Price:€69 / night
Cameron Charmer
SUPERHOSTEntire house
Cameron Charmer
Price:€97 / night
Lovely Private Room
SUPERHOSTPrivate room
Lovely Private Room
Price:€19 / night
The Inwood House- easy on/off I-81
SUPERHOSTEntire house
The Inwood House- easy on/off I-81
Price:€80 / night
Arden House, Inwood WV
SUPERHOSTEntire house
Arden House, Inwood WV
Price:€53 / night
Majestic Mountain Cabin
SUPERHOSTEntire cabin
Majestic Mountain Cabin
Price:€133 / night
Private efficiency apartment
SUPERHOSTEntire apartment
Private efficiency apartment
Price:€71 / night
The Dome at Our Farm
SUPERHOSTDome house
The Dome at Our Farm
Price:€84 / night
Retro Vibe Studio
Entire guest suite
Retro Vibe Studio
Price:€62 / night
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