
Apartment vacation rentals in Winchester
Find and book unique apartments on Airbnb
Top-rated apartment rentals in Winchester
Guests agree: these apartments 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 apartment rentals
Weekly apartment rentals

Apt near i81/hiking/wineries

A Place to Rest

Top Rated Luxe 2BR Apartment-Full Kitchen/Laundry

Easy like a Sunday Morning 1 BR apt great location

The Eagles Nest

Spacious Charming Basement Apt

The Speakeasy Listening Room

Two Bdrm. Flat w/ Patio Terrace
Private apartment rentals

Owl’s Nest at Shiloh

Whole Garage Apartment with Blue Ridge Views

Woodpecker~Downtown~Main Street~Near Park & River

The Downtown Flat at Creekside

Brent House | Downtown Frederick

Romantic Wine Country Suite | Polo, Hiking Retreat

Charming Spacious Luxury Apt

The Potomac Perch-Peaceful Cozy Family Apt
Apartment rentals with a hot tub

Massanutten Cozy Apartment with Hot Tub & Jacuzzi

Hot Summer DEALS at Mockingbird Mt Spa and Retreat

West Virginia Gold (lower unit)

Blue Skies & Mountain Views w/ Hot Tub - 2 bdrm

Beautiful Massanutten 2BDR-Condo

Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks

Azul Apt

Country calm and close to city
Quick stats about apartment rentals in Winchester
Total rentals
40 properties
Nightly prices starting at
$41 CAD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Destinations to explore
- Plainview Vacation rentals
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- House rentals Winchester
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- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Apartment rentals Virginia
- Apartment rentals United States
- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Cacapon Resort State Park
- Shenandoah Valley Golf Club
- Gambrill State Park
- Robert Trent Jones Golf Club
- Creighton Farms
- Berkeley Springs State Park
- Whitetail Resort
- South Mountain State Park
- Bryce Resort
- Sly Fox Golf Club
- River Creek Club
- Bowling Green Country Club
- Notaviva Vineyards
- Dinosaur Land
- Twin Lakes Golf Course
- Reston National Golf Course
- Car and Carriage Caravan Museum
- JayDee's Family Fun Center
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Warden Lake