Skip to content

Winchester vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Winchester

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

Superhost
Cottage in Winchester
Fall Season Cottage Escape! Hot Tub*Privacy*Views!
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...
$180 per night
Superhost
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.
$125 per night
Superhost
Apartment in Winchester
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.
$123 per night

Stay near Winchester's top sights

Walmart Supercenter4 locals recommend
Old Town Winchester25 locals recommend
Costco Wholesale3 locals recommend
Apple Blossom Mall station14 locals recommend
Shenandoah Valley Discovery Museum34 locals recommend
Museum of the Shenandoah Valley72 locals recommend

Other great vacation rentals in Winchester

Superhost
Home in Winchester
Newly Renovated Cozy Cottage
$79 per night
Superhost
Cabin in Berkeley Springs
+ The Cabin + @ Camp Potomac Peak
$207 per night
Superhost
Home in Winchester
City Charmer minutes from Old Town
$106 per night
Superhost
Apartment in Winchester
Pretty Little Apt by the Train II
$126 per night
Superhost
Cabin in Strasburg
Cedar River Retreat~ River Access~Hot Tub~King Bed
$161 per night
Superhost
Cabin in Berkeley Springs
Dreamtime - Modern A-Frame Cabin w/ Hot tub
$240 per night
Superhost
Cabin in Winchester
Majestic Mountain Cabin
$150 per night
Superhost
Home in Winchester
Cameron Charmer pristine w/double master suites
$184 per night
Superhost
Home in Front Royal
SUNSET/RIVER VIEWS, Secluded mountain chalet with hot tub, newly decorated, king beds, 3 fireplaces, 20 mins to parks, canoeing, Skyline Drive, wineries, breweries and more!!
$201 per night
Superhost
Condo in Winchester
Historic District Downtown Winchester
$169 per night
Superhost
Apartment in Winchester
Historic Wisteria House on Old Town Walking Mall
$139 per night
Superhost
Apartment in Winchester
Brooklyn Rhapsody 1BR king w/office downtown apt
$131 per night

Destinations to explore

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