
Apartment vacation rentals in Winchester
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Top-rated apartment rentals in Winchester
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A Great Getaway — Foxglove Retreat
Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

The Comfortable In-Towner
A cute one bedroom apartment located on lower level of a historic 1840s home. This half basement has windows to let in natural light, a full-size kitchen with dishwasher, fridge, big closets, Queen size Tuft & Needle premium mattress and a private screened patio open to our courtyard with friendly neighbors and management on site. Window ac units, fans & radiators Quiet neighborhood in Old Town Winchester, Va, two short blocks from pedestrian mall with restaurants, shops cafes & entertainment.

Nostalgia Lane 3 BR in the heart of the city
Steps from the Walking Mall this 2nd floor apartment is in a vintage Tudor style building overlooking the downtown city street. Its space is light & airy full of charm & it’s spacious-3 bedrooms will make for a fabulous stay. You can park & spend your time enjoying the local breweries the iconic John Handley Library, the Discovery Museum, delicious restaurants, galleries & shops just outside your door. Nostalgia Lane has a wonderfully peaceful relaxing vibe —You will love it ! Happy Travels!

Modern Twist in Old Town! Rock n' Roll FUN!
Basil is your personal, 2 bedroom, Uber-stylish apartment, located in downtown Winchester with private parking! New & sparkling clean, enjoy high end finishes & creative design! Enjoy hot showers in the marble bath, sink into the shearling-covered couch relaxing in front of the new 55' smart TV, catch up with work in your private office, then walk to a great happy hour & dinner downtown! End your day cozying up in one of the two queen size, memory foam canopy beds! Basil is your perfect Airbnb!

Old Town 1920s Gas Station with Hot Tub
1920s Refurbished Gas Station with hot tub repurposed into a beautiful luxury apartment. Private parking/EV charging, private hot tub, full kitchen, custom rain shower, high speed wifi and smart TV. There is plenty of light with frosted garaged doors, all modern appliances, laundry and coffee nook in an open living design. Be a part of Old Town Winchester in this unique getaway, walking distance to shops, downtown eateries and our neighborhood Pizzoco Pizza Parlor one block away. Pets welcome!

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.

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.

Cozy 1BR for Couples & Solo Travel~No Cleaning Fee
Welcome to Cozy Hideaway, your Shenandoah Valley retreat! Enjoy an upstairs space with a queen bed, full bath, washer/dryer, and mini kitchenette with microwave and fridge. Local art adds charm. With a private 2nd-floor entry, you’re near the Shenandoah River for fishing and kayaking, and 8 mins from Skyline Drive—perfect for nature lovers. Guests like Steve (Aug 2024) say: 'Fun, friendly, comfy, affordable—you do Airbnb right!' Note: Stairs required; we’ll help with bags if you’d like.

Rose End
Need to social distance? Our quiet country studio is far enough from Washington DC to get away without being gone. Ideal for grabbing some space, a long run, a bike ride, or visiting local wineries. The Appalachian Trail is just a stone's throw away. We respect your privacy. No smoking is allowed and internet access is from your own hot-spot. The studio includes a satellite TV, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

The 1763 House - Stay in Downtown Shepherdstown
Welcome to our charming downtown Shepherdstown apartment, originally built in 1763 and nestled in the heart of town. Ideal for getaways, visiting family/friends, or university trips. Enjoy a spacious interior, comfortable living room, state-of-the-art kitchen, and private patio. Our downtown location on the Main Street offers convenient access to a wide selection of restaurants, unique shopping, and the Potomac river, all just a short walk away!

Newly repurposed Historic Home in Winchester VA!
The historic “Homespun” is located on the border between Frederick County and the city of Winchester. Originally built in the mid 1790’s the Homespun is significant in local architecture as an example of a dogtrot-plan structure, a rare building form of this period. The property is listed on the National register of Historic Places and Virginia Landmark Registry.

The Lodge at Turkey Creek
Your low tech getaway awaits in the VA Piedmont wine & hunt country! Nestled in the woods at the end of a half mile private drive you will find peaceful quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, charming towns, idyllic scenery, mountains and wineries.
Popular amenities for Winchester apartment rentals
Weekly apartment rentals

Lovely 1100 Sq. ft. 1 bedroom basement apartment

Apt near i81/hiking/wineries

Woodpecker/Downtown~Main Street~Near Park & River

Newtown Cozy Cottage Basement

The Eagles Nest

Spacious Charming Basement Apt

Studio 203

The Speakeasy Listening Room
Private apartment rentals

Owl’s Nest | King Bed | Wine Country Apartment

"Over The Ridge" Vintage Modern Apartment

Whole Garage Apartment with Blue Ridge Views

The Downtown Flat at Creekside

Romantic Wine Country Suite | Polo, Hiking Retreat

Carroll Creek Private Apt./Luxury King Bed

Garden Apt: Enjoy Nature & Walk to Wineries

Charming Spacious Luxury Apt
Apartment rentals with a hot tub

Massanutten Cozy Apartment with Hot Tub & Jacuzzi

Relax and restore at Mockingbird spa and retreat

West Virginia Gold (lower unit)

Harpers Ferry Apartment w/ Private Pool & Hot Tub!

Massanutten Resort. 2BR/2BA Jacuzzi Waterpark/Golf

Rockwell Suite #201 at the Inns at Whitetail

Beautiful Massanutten 2BDR-Condo

The Parlor Suite
Quick stats about apartment rentals in Winchester
Total rentals
40 properties
Nightly prices starting at
$42 CAD before taxes and fees
Total number of reviews
3.8K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Shenandoah Valley Golf Club
- Cacapon Resort State Park
- Gambrill State Park
- Berkeley Springs State Park
- Whitetail Resort
- Creighton Farms
- Bryce Resort
- Robert Trent Jones Golf Club
- South Mountain State Park
- River Creek Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Bowling Green Country Club
- Dinosaur Land
- Car and Carriage Caravan Museum
- Twin Lakes Golf Course
- JayDee's Family Fun Center
- Reston National Golf Course
- Warden Lake
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course