Skip to content

Vacation rentals in Winchester

Find and book unique accommodations on Airbnb

When results are available, navigate with up and down arrow keys or explore by touch or swipe gestures.

Top-rated vacation rentals in Winchester

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

Guest favourite
Cottage in Winchester
Private Winter Escape! Hot Tub*Views*Sexy!
Disentangle and Unwind at Foxy, your exclusive cottage retreat located in the Shenandoah Valley, surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge yourself in luxury and tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...
Guest favourite
Apartment in Winchester
Old Town Loft In Highly Desirable Area Downtown
Location, Location! A completely renovated apartment in the highly desirable center Winchester. You’ll still be able to see some of its original character throughout this historic building. The apartment has a fully stocked custom kitchen with reclaimed wood and quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, queen memory foam mattress, high speed Wi-Fi, 50’ smart TV, Xfinity HDTV with voice remote control, AC/Heat, Washer/Dryer, and dishwasher.
Guest favourite
Apartment in Winchester
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.

Popular amenities for Winchester vacation rentals

Stay near Winchester's top sights

Old Town Winchester25 locals recommend
Walmart Supercenter4 locals recommend
Costco Wholesale3 locals recommend
Shenandoah Valley Discovery Museum34 locals recommend
Apple Blossom Mall station14 locals recommend
Papermill Place4 locals recommend

Other great vacation rentals in Winchester

Guest favourite
Apartment in Winchester
Pretty Little Apt by the Train II
Guest favourite
Cabin in Strasburg
Cedar River Retreat~ River Access~Hot Tub~King Bed
Guest favourite
Cottage in Winchester
Emma's Stone Cottage
Guest favourite
Home in Winchester
Cameron Charmer pristine w/double master suites
Guest favourite
Home in Inwood
The Inwood House- easy on/off I-81
Guest favourite
Home in Front Royal
Hot tub w/ Sunset Views! Secluded mountain chalet
Guest favourite
Cabin in Winchester
Majestic Mountain Cabin
Guest favourite
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
Guest favourite
Cabin in Front Royal
The Wizard's Chalet • Cozy cabin escape w/ Hot Tub
Guest favourite
Condo in Winchester
Historic District Downtown Winchester
Guest favourite
Home in Winchester
Cabin in Historic Old Town Winchester
Guest favourite
Guest suite in Winchester
Retro Vibe Studio

Quick stats about vacation rentals in Winchester

Total rentals

90 properties

Wifi availability

90 properties include access to wifi

Rentals with dedicated workspaces

60 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

5.7K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Virginia
  4. Winchester