Skip to content

Winchester cabins

Book unique cabins, vacation rentals, and more on Airbnb

Top-rated cabins in Winchester

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

SUPERHOST
  1. Entire cabin
  2. Winchester
Majestic Mountain Cabin

Spectacular 100 mile panoramic view from the top of Big Bear Mountain. This well appointed cabin has an open floor plan with an updated kitchen and breakfast bar with seating for four. Living room has comfortable furnishings and a wood burning fireplace with raised hearth. Two spacious bedrooms and custom bathroom. Watch the sunrise and sunset over Shenandoah Valley from the wrap around deck. Comfortable outdoor furniture for relaxing. Close to wineries and historic downtown Winchester.

$150 per night
SUPERHOST
  1. Entire cabin
  2. Strasburg
Strasburg Cabin Hideaway!

New Listing-just renovated **4/2022 Peaceful cabin getaway. Pet friendly, grill and hot tub! Approximately 12 minutes from the town of Strasburg, antique capital of Virginia. Hallmark-esque town, quiet and peaceful, great retreat if you’re looking to get away from the city or hiking in the Shenandoah’s. Close to Woodbine Farms And the best coffee at Nancy’s coffee shop. Rain shower, high tech water filtration system. Relax and grill out, play games, etc.

$160 per night
SUPERHOST
  1. Entire cabin
  2. Augusta ( Capon Bridge)
Nirvana, Mountain View

One bed room cabin. Beautiful view , peaceful environment, private, quiet, fresh air, country living, great place for meditation, Everyday sunset view ! Beautiful green and wood surrounding in the spring , summer, golden leaves in the fall season and Snow white and cold in the winter. Minimum 7 days.

$65 per night

Vacation rentals for every style

Get the amount of space that is right for you

  • Cabins
  • Hotels
  • Unique stays

Stay near Winchester's top sights

Photo of Museum of the Shenandoah Valley
Museum of the Shenandoah Valley30 locals recommend
Photo of Shenandoah Valley Discovery Museum
Shenandoah Valley Discovery Museum18 locals recommend
Photo of Brightbox Theater
Brightbox Theater11 locals recommend
Photo of Handley Regional Library
Handley Regional Library3 locals recommend
Photo of Patsy Cline Historic House
Patsy Cline Historic House4 locals recommend
Photo of Old Town Winchester
Old Town Winchester9 locals recommend

Vacation rentals in Winchester

  1. Entire loft
  2. Winchester
Immerse yourself in Old Town Winchester
$77 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Downtowner
$123 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Downtown Renovated 1920's Gas Station
$120 per night
  1. Entire loft
  2. Winchester
Immerse Yourself in Old Town #3
$76 per night
  1. Entire rental unit
  2. Winchester
Historic Wisteria House on Old Town Walking Mall
$134 per night
  1. Entire home
  2. Winchester
Historic District Charm On Cameron Street
$150 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
The New Yorker Quiet tucked away 1BR walk to town
$112 per night
SUPERHOST
  1. Entire townhouse
  2. Winchester
Modern Elegance in Historic Old Town Winchester
$123 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Dreamweaver Bright 1BR 2 blocks to Walking Mall
$128 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Pretty Little Apt by the Train II
$113 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
Rosamond downtown studio apt w/free parking
$101 per night
SUPERHOST
  1. Entire rental unit
  2. Winchester
The Blue Door steps from Handley Library
$109 per night

Weekly rentals in Winchester

SUPERHOST
  1. Entire cabin
  2. Augusta
Bodhi, Mountain View
$43 per night
SUPERHOST
  1. Entire cabin
  2. Berkeley Springs
Dreamtime - Modern A-Frame Cabin w/ Hot tub
$265 per night
SUPERHOST
  1. Entire cabin
  2. Paw Paw
Easygoing
$100 per night
  1. Entire cabin
  2. Capon Bridge
Secluded Mountain Top Cabin w/hot tub+Pool tbl+Wif
$139 per night
SUPERHOST
  1. Entire cabin
  2. Rileyville
**HIDEAWAY CABIN** Unique small-cabin experience!
$216 per night
SUPERHOST
  1. Entire cabin
  2. Berkeley Springs
Hot Tub, Huge Deck, WiFi, Fire Pit at Chalet Cabin
$149 per night
SUPERHOST
  1. Entire cabin
  2. Rileyville
Clouds Cabin
$238 per night
SUPERHOST
  1. Entire cabin
  2. Strasburg
Fall in LOVE@ AVA! Iconic A-frame w/HOT TUB+RIVER!
$200 per night
SUPERHOST
  1. Entire cabin
  2. Strasburg
Cedar River Retreat~ River Access~Hot Tub~King Bed
$189 per night
  1. Entire cabin
  2. Harpers Ferry
Applemoon: Charming Log Cabin in a Mountain Lake Community
$186 per night
  1. Entire cabin
  2. Berryville
Two Spruce Log Cabin-Berryville
$246 per night
  1. Entire cabin
  2. Luray
Whispering Woods~Renovated~Walk to River~Hot tub
$257 per night
  1. Airbnb
  2. United States
  3. Virginia
  4. Winchester