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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.

  • Downtowner
    SUPERHOSTEntire apartment · 4 guests · 3 beds · 1 bath
    Downtowner

    No hassle parking on premises and a private entrance. The "Downtowner" is a 1920's era restored home in a quiet residential section of Winchester's Historic District and just a short stroll to the downtown "pedestrian only" walking mall with restaurants, cafes, and shops. Clean and spacious, the apartment is complete with bed linens, towels, etc. and stocked with water in the fridge as well as a Keurig with coffee options, tea, hot chocolate, etc...Xfinity HDTV with voice remote control.

    What guests are saying:

    “This apartment is an amazing find. So close to historic Old Winchester where we ate frequently. In a beautiful and safe part of town, the apartment looks like it is brand new because it is so clean and decorated in an up-to-date manner. The four of us were very comfortable in the spacious bedrooms, sparkling clean bathroom and well laid out kitchen/dining/living space. It is so close to the beautiful hills of northern Virginia and historic/tourist attractions.”

  • 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!”

  • City Charmer minutes from Old Town
    SUPERHOSTEntire house · 6 guests · 3 beds · 1 bath
    City Charmer minutes from Old Town

    Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

    What guests are saying:

    “My family and I had a great stay at Crystal's place. The home was sparkling clean and the beds were very comfortable. We immediately felt cozy and were able to relax after arriving from a long drive to Winchester. The house is perfectly located for getting to stores and restaurants. We easily parked two vehicles in front of the home (on street) and these spots were open each time we returned. Crystal responded quickly to messages and reached out to make sure our stay was going well. Highly recommend this home for your stay in Winchester!”

Vacation rentals for every style

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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

ANS Inn & Suites (Efficiency Suites)
Entire guest suite
ANS Inn & Suites (Efficiency Suites)
Price:€43 / night
Immerse yourself in Old Town Winchester
Entire loft
Immerse yourself in Old Town Winchester
Price:€54 / night
A place that feels like home
Room in boutique hotel
A place that feels like home
Price:€39 / night
The Millwood House
Entire house
The Millwood House
Price:€117 / night
One Bedroom Apt in DownTown Winchester
SUPERHOSTEntire apartment
One Bedroom Apt in DownTown Winchester
Price:€66 / night
Quiet but In-Town Getaway
SUPERHOSTEntire apartment
Quiet but In-Town Getaway
Price:€59 / night
Safe, cozy oasis with private living & bath.
Entire guest suite
Safe, cozy oasis with private living & bath.
Price:€45 / night
Get Your Stay On w/Free Wifi, Breakfast, and Lunch
Private room
Get Your Stay On w/Free Wifi, Breakfast, and Lunch
Price:€23 / night
Pretty Little Apt By the Train II
SUPERHOSTEntire apartment
Pretty Little Apt By the Train II
Price:€70 / night
City Charmer minutes from Old Town
SUPERHOSTEntire house
City Charmer minutes from Old Town
Price:€71 / night
Private room for Rent (Min 30 days)
Private room
Private room for Rent (Min 30 days)
Price:€18 / night
ANS Inn and Suites Efficiencies
Hotel room
ANS Inn and Suites Efficiencies
Price:€41 / night
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