
Condo vacation rentals in Winchester
Find and book unique condos on Airbnb
Top-rated condo rentals in Winchester
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester condo rentals
Weekly condo rentals

“Osprey’s Nest” cozy condo escape Bryce Resort

2 Bedroom Condo - Snow Tubing, Ski!

Massanutten Woodstone or Summit 4BR, 4BA

Luxury 2BR 2BA w Hot Tub bath at Massanutten

Cozy 2-bedrooms condo in the heart of Stafford

2 Bed Condo at Abolitionist Ale Works #300

Lovely 3 Bed Room Condo with Free Parking

Massanutten Summit 2 BEDRM Luxury Condo w/Jacuzzi
Pet-friendly condo rentals

Luxury Condo In Downtown Frederick

Farm house suite!

Ski🎿 & hike from front steps—Mountainside getaway

Private 2/2 full baths very bright basement home

Lark's Nest on Market

3 bedroom Condo near IAD-walk to downtown Herndon!

Perfect Location Old town / walk to the metro

The Cozy Villa
Condo rentals with a pool

Beautiful Reston's Home

Avalon Resort Paw Paw WV Condo

The Music Room at Ski Whitetail!

Aspen East 313/314 -- SKI-IN/SKI-OUT!
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- Bryce Resort
- Whitetail Resort
- Luray Caverns
- Cacapon Resort State Park
- Stone Tower Winery
- South Mountain State Park
- Car and Carriage Caravan Museum
- Robert Trent Jones Golf Club
- Twin Lakes Golf Course
- Bowling Green Country Club
- Dinosaur Land
- Shenandoah Valley Golf Club
- Sly Fox Golf Club
- JayDee's Family Fun Center
- Berkeley Springs State Park
- Notaviva Vineyards
- Gambrill State Park
- River Creek Club
- Creighton Farms
- Herndon Centennial Golf Course
- Cunningham Falls State Park
- Hidden Creek Country Club
- Reston National Golf Course
- The Golf Club at Lansdowne
- Family travel hub Tips and inspiration
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- Kid-friendly state parks Check out these family-friendly hikes