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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.

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Top guest favorite
A contemporary building with a mix of stone and modern gray walls is showcased, featuring large glass windows and wooden accents. A bright yellow door provides a pop of color at the entrance. The surrounding area includes wooden railings and landscaped greenery.
Apartment in Winchester
4.91 out of 5 average rating, 409 reviews

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!

Top guest favorite
A comfortable seating area features a gray sofa positioned against exposed brick walls. A tan upholstered bench serves as a coffee table in front of the couch, while a light accent lamp provides illumination. Hardwood floors add warmth to the space.
Apartment in Winchester
4.99 out of 5 average rating, 251 reviews

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.

Guest favorite
A cozy living area is furnished with a sofa and an accent chair, positioned around a coffee table. A warm fireplace complements the space, while a dining area with a table and chairs is visible in the background. Soft lighting enhances the inviting ambiance.
Apartment in Winchester
4.9 out of 5 average rating, 136 reviews

Scarborough Fair walk to downtown two story apt

Come to downtown Winchester get the true feel of the city. Park & Walk to beautiful Handley Library, take a stroll to the much loved walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three bedrooms, two levels, three porches, fenced yard. Eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? or have any additional questions? Reach out on social media: Michele Bouve Hoffman.

Top guest favorite
The exterior of a modern barn features a combination of dark and light siding, with large windows and double doors at the center. A landscaped area with grass and trees surrounds the structure, with a gravel pathway leading to the entrance.
Apartment in Leesburg
4.99 out of 5 average rating, 192 reviews

The Barn at Belgrove

The Barn at Belgrove. Welcome to a private and quiet escape on a 67 acre manor in Leesburg. A horse property with abundant wildlife offers a peaceful getaway on an historic property. This full apartment is located above the barn. It is convenient to downtown Leesburg, Morven Park, and Loudoun's many wineries, breweries and festivals. Most suitable for adults seeking to relax, recharge, and rekindle in a rustic environment. There is generally very good cell service but there is no Wifi.

Guest favorite
A cozy living room features a modern grey couch with decorative pillows, flanked by two side tables with lamps. A wooden coffee table sits at the center, and colorful framed artwork adorns the dark blue wall. A plush rug covers the floor, enhancing the inviting atmosphere.
Apartment in Shepherdstown
4.93 out of 5 average rating, 380 reviews

1 Bedroom Apt in Historic Downtown Shepherdstown

Live like a local in our newly renovated, one-bedroom apartment in the heart of downtown Shepherdstown. Comfortably blending modern conveniences with historic charm, the 2nd floor apartment – which features space for no more than 3 guests – is located in a 100-year-old building directly behind Shepherd University's campus on German Street. Walk to the town’s restaurants, shops, and the university during Theater season, sporting events, or graduation. Comes with one free parking space

Top guest favorite
A charming view of downtown Shepherdstown showcases a row of historic buildings, each displaying unique architectural features. A vibrant green tree adds a touch of nature, while a clear blue sky enhances the picturesque streetscape.
Apartment in Shepherdstown
4.97 out of 5 average rating, 263 reviews

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!

Top guest favorite
A table set with checkered linens is surrounded by rustic wooden chairs, situated on a lush green lawn. In the background, a two-story home features a blend of contemporary and rustic design, with prominent windows and a sloped metal roof.
Apartment in Marshall
4.96 out of 5 average rating, 200 reviews

The Lodge at Turkey Creek

Your low-tech getaway awaits in the heart of the coveted Virginia Piedmont horse & wine country! Nestled in the woods at the end of a half mile private drive you will find quiet & solitude. Your tranquil sanctuary includes a charming lower level apartment and patio. Located in the midst of expansive horse farms, quaint towns, idyllic scenery, mountains and wineries. Only 40 min to Shenandoah Nat’l Park & 20 min to Sky Meadows State Park.

Top guest favorite
A compact dining area features a round wooden table with a colorful tablecloth. Two wooden chairs with dark upholstery are positioned around the table. Natural light enters through two windows covered with sheer black curtains, creating a welcoming and bright atmosphere.
Apartment in Woodstock
4.88 out of 5 average rating, 638 reviews

Heart of Town-Pet Friendly

This apartment is in a older home located in heart of town. Walking distance to Resturants, Brewhouse, Shops, Theatre, and town events, Location is great. I have my business in this house on lower level. The apartment has it's own entrance. It has 3 rooms and a bath. I love this house and want to share it. Think you will love it too.

Top guest favorite
A well-appointed outdoor space features a private cedar barrel sauna, complemented by a small dining table with two yellow chairs. Greenery surrounds the area, and a patterned outdoor rug adds texture to the wooden deck, creating a relaxing environment for guests.
Apartment in Berkeley Springs
5 out of 5 average rating, 118 reviews

The Downtown Flat at Creekside

Welcome to the Downtown Flat at Creekside, brought to you by Camp Potomac Peak! Located in the heart of downtown Berkeley Springs, take a walk to the park, grab some food--or a beer at the local brewery, and then relax back at your upstairs oasis--complete with cedar barrel sauna, and two outdoor decks to take it all in.

Superhost
A spacious bedroom is illuminated by natural light from two large windows. A comfortable bed is styled with soft linens and a warm blanket. Two armchairs sit invitingly in the corner, and textured rugs decorate the hardwood floor.
Apartment in Charles Town
4.8 out of 5 average rating, 110 reviews

Spacious apt with King beds in DT Charles Town

Welcome to our charming 2-bedroom Airbnb in downtown Charles Town, WV! This modern retreat offers two spacious bedrooms with king-size beds for a comfortable stay. Explore the city's attractions and enjoy a cozy night's sleep in stylish accommodations. Book now for a memorable stay in the heart of Charles Town!

Top guest favorite
The living area features a dark, comfortable sofa adjacent to a round coffee table. Large windows allow natural light to fill the space, framed by sheer curtains. A colorful area rug with floral patterns covers the floor, contributing to the room's welcoming ambiance.
Apartment in Hagerstown
4.99 out of 5 average rating, 103 reviews

The Violet Femme Studio

This apartment is a glamorous second floor walk-up studio with a full kitchen, 3/4 bath, with a private foyer and back balcony porch that is located in a historic district. It is walking distance from the downtown area and one of the most beautiful city parks in the USA.

Guest favorite
The exterior of a two-story efficiency apartment is visible, featuring a green metal roof and white siding. A small dormer window protrudes from the roofline, and exterior steps lead up to a private entrance. Outdoor light fixtures adorn the facade, enhancing visibility.
Apartment in Charles Town
4.97 out of 5 average rating, 652 reviews

Private efficiency apartment

We have been an Airbnb host for many years. Butch is a retired teacher and pastor, keeps busy with handyman jobs. Beth works full time taking care of Butch. Our daughter, Lynn, is our co-host taking care of the "Nest" when we are in Florida.

Popular amenities for Winchester apartment rentals

When is the best time to visit Winchester?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$26,150 GYDG$25,313 GYDG$27,196 GYDG$24,685 GYDG$27,196 GYDG$25,522 GYDG$26,150 GYDG$25,522 GYDG$24,895 GYDG$25,313 GYDG$25,522 GYDG$26,150 GYD
Avg. temp1°C3°C7°C13°C18°C23°C25°C24°C20°C14°C8°C3°C

Quick stats about apartment rentals in Winchester

  • Total vacation rentals

    Explore 50 vacation rentals in Winchester

  • Nightly prices starting at

    Winchester vacation rentals start at G$8,368 GYD per night before taxes and fees

  • Verified guest reviews

    Over 4,180 verified reviews to help you choose

  • Family-friendly vacation rentals

    20 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Winchester vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Winchester rentals

  • 4.8 Average rating

    Winchester stays are highly rated by guests—averaging 4.8 out of 5!

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