Apartment holiday rentals in Winchester

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.

4.91 out of 5 average rating, 422 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!

LocationFamilyLayout

4.98 out of 5 average rating, 131 reviews

A modern living area is highlighted by a comfortable sectional sofa adorned with colorful cushions. A round coffee table sits in front, with a decorative item placed on top. Large windows allow natural light to illuminate the space, framed by soft curtains and offering views of greenery outside.

Apartment in Sterling

The Potomac Perch-Peaceful Cozy Family Apt

Step into a calming and contemporary haven. This thoughtfully designed one-bedroom apartment features a spacious bedroom with full bathroom , a modern full kitchen perfect for preparing your favorite meals, and comfortable living areas. The bright and airy layout, with its clean lines and tasteful decor, creates an inviting atmosphere for relaxation after a day of exploring. Nestled in a quiet and peaceful neighborhood along Broad Run Drive, you'll be just moments from the scenic Potomac River.

LocationValueBathroom

4.98 out of 5 average rating, 725 reviews

A spacious bedroom features a queen-size bed adorned with decorative pillows. Natural light enters through a skylight and windows. A television is positioned against a wall, accompanied by a combination of vintage and modern furniture pieces, creating a cozy and inviting atmosphere.

Apartment in The Plains

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, wi-fi, refrigerator, microwave, and coffee maker. The queen-size bed and skylight make Rose End a cozy escape.

LocationFamilyBackyard

Aerial view captures the historic downtown Winchester at sunset, with buildings showcasing varied architectural styles. The warm glow of the sun illuminates the skyline, highlighting the rooftops and the distinctive features of the surroundings. Streets lined with trees provide a scenic backdrop.

4.91 out of 5 average rating, 279 reviews

Downtown FUN! Personal Mid Century 2bd Apartment!

Welcome to Blossom! Your own, private pied-à-terre, located in Winchester's historic district, 1 block from the Old Town Walking Mall! Blossom's UBER-LUX upgrades include a fully-stocked custom kitchen, marble countertops, new stainless steel appliances, high speed internet, gleaming hardwood floors, queen size canopy beds, heavenly memory foam mattresses, 50' smart TV, all delivered with a Euro MCM flare! Blossom is ideal for a romantic getaway, smart business travel, or a quick City escape!

LocationFamilyGetting around

A spacious dining area features a wooden table with woven placemats, surrounded by upholstered chairs. Natural light fills the room through the windows. A comfortable seating arrangement with a sofa is visible in the background, complemented by a television on a console.

4.97 out of 5 average rating, 359 reviews

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.

LocationValueLong stay

The living area features a spacious sectional sofa positioned around a round coffee table. A soft area rug lies beneath. Natural light filters through multiple windows with blinds, illuminating the hardwood floors. A decorative plant adds a touch of greenery, while a lamp provides warm lighting.

4.98 out of 5 average rating, 161 reviews

Old Town Loft Modern Oasis In Downtown Winchester

Location, Location! A completely renovated, 2 bed/1 bath, 1100 sq. ft. apt in the highly desirable center of 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 quartz counters, coffee nook with Keurig, large tile shower with glass doors, hardwood floors, memory foam mattresses, high speed Wi-Fi, 60’ smart TV, Xfinity HDTV, AC/Heat, Washer/Dryer, dishwasher and 2 free parking spaces.

ValueFamilyKitchen

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.

4.93 out of 5 average rating, 401 reviews

Downtown - 1BR Apartment on E. German St

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

ValueLocationWi-Fi

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.

4.98 out of 5 average rating, 285 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!

LocationValueAccess

4.96 out of 5 average rating, 220 reviews

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

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.

FamilyLocationSolo travel

A light-filled living area features a cream-colored sofa with yellow accent pillows and a patterned ottoman. A dining table with chairs is visible in the background, along with a large window allowing natural light to illuminate the space.

4.95 out of 5 average rating, 130 reviews

Easy like a Sunday Morning 1 BR apt great location

You will enjoy easy access to everything from this centrally located apartment. Comfortable, easy-going yet stylish, light-filled apartment on the 2nd floor of a historic 1840s home with terrific neighbors just two short-walking blocks to the Old Town Winchester pedestrian mall with shops, restaurants, coffee cafes, museums, entertainment, breweries and wine bars.

LocationValueBiking

4.99 out of 5 average rating, 101 reviews

A spacious living area features a modern sofa and a comfortable lounge chair, complemented by a coffee table. A dining table with four chairs is positioned near a window, while greenery adds a touch of nature. Soft light filters through the windows, enhancing the serene atmosphere.

Apartment in Cumberland

Corner Tavern-Allegheny Suite

Nestled above Corner Tavern & Cafe in historic downtown, this newly renovated modern apartment supplies you with all the comforts of home in a tasteful design. Our location provides all the benefits of a night out of town, located in historic downtown, above a tavern & cafe, you'll find food, drink & maybe even music in a few short steps from your apartment.

LocationValueWalkability

4.88 out of 5 average rating, 669 reviews

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

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.

ValueFamilyBathroom

Popular amenities for Winchester apartment rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Weekly apartment rentals

The open kitchen features dark cabinetry and modern appliances, including an oven and refrigerator. A round dining table with two bar stools is positioned nearby. A patterned area rug and two coffee tables add a cozy touch to the living space, with warm wood flooring throughout.

4.96 out of 5 average rating, 461 reviews

Downtown: Explore Shepherdstown from cozy 1br apar

LocationValueRiver

Apartment in Harpers Ferry

The exterior of a contemporary home is showcased, featuring large windows that allow natural light to filter inside. Surrounding the entrance, colorful planters filled with various plants add a touch of greenery to the gravel pathway.

4.96 out of 5 average rating, 196 reviews

The Boundary House Apartment

ValueFamilyCheckout

Apartment in Falling Waters

4.95 out of 5 average rating, 242 reviews

Near I-81, but private! Laundry! No fees!

ValueFamilyParking

4.99 out of 5 average rating, 625 reviews

A spacious bedroom is furnished with a wooden bed featuring a patterned quilt. Soft lighting is provided by two bedside lamps. A small window is dressed with a plant on the sill, allowing natural light to brighten the inviting space.

Apartment in Cumberland

Steeple View Flat in Historic District

LocationValueOutdoor spaces

5.0 out of 5 average rating, 226 reviews

The exterior of The Quarters at Belgrove is showcased, featuring a charming white facade with decorative paneling. Two large garage doors and a welcoming entrance are visible, complemented by planters filled with vibrant flowers. Natural greenery surrounds the property, enhancing its serene setting.

Apartment in Leesburg

The Quarters at Belgrove

LocationFamilyHeating

5.0 out of 5 average rating, 202 reviews

A contemporary living space features a living area with a gray sofa and a wooden coffee table, complemented by a side lamp. A dining table with place settings is positioned alongside an equipped kitchen, while a cozy rug ties the room together. Large windows allow natural light to fill the space.

Apartment in Sperryville

Stonewall Abbey Apartment

FamilyLocationNearby

4.98 out of 5 average rating, 508 reviews

A light-filled living area features a comfortable sofa and armchair, complemented by a patterned area rug. Two large windows allow natural light to illuminate the space. A television sits on a dark wooden cabinet, adding to the welcoming atmosphere.

Apartment in Leesburg

Historic Leesburg location with so much more!

ValueLocationCondition

4.99 out of 5 average rating, 181 reviews

A covered patio area is presented with a picnic table and a decorative rug. Lush flower beds filled with vibrant blooms line the space, adding color and charm. A small wooden chair enhances the inviting outdoor setting.

Apartment in Hagerstown

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5

ValueFamilyAmenities

Private apartment rentals

Apartment in Harrisonburg

A serene outdoor scene features a small fish pond surrounded by smooth stones and lush greenery. A hammock is suspended between two trees, inviting relaxation. Sunlight filters through the leaves, casting gentle shadows on the natural landscape, enhancing the peaceful ambiance.

4.91 out of 5 average rating, 860 reviews

Restful Hilltop Apartment: No cleaning fees!

LocationValueWalkability

4.99 out of 5 average rating, 276 reviews

The living area features a light wood floor with a colorful area rug. A blue armchair and a patterned sofa provide comfortable seating. A dining table with black chairs stands nearby, and a small bookshelf holds various games and books. Sliding glass doors offer access to the patio.

Apartment in Broadway

Shenandoah Valley apartment with view

ValueFamilyComfort

4.98 out of 5 average rating, 145 reviews

A cozy living area is equipped with a vibrant yellow armchair and a light gray sectional sofa. A large screen TV is mounted on the wall, and natural light enters through a window adorned with white curtains. A round wooden coffee table sits on a patterned area rug.

Apartment in Culpeper

Red Fox Retreat

ValueLocationHospitality

4.97 out of 5 average rating, 288 reviews

A lush green landscape features a large tree and a pond, with a winding road framed by wooden fencing. Surrounding foliage adds to the serene setting, creating a peaceful outdoor environment.

Apartment in Bentonville

Full Circle Farm Shenandoah Valley No Cleaning Fee

ValueLocationLaundry

Apartment in Purcellville

A comfortable living room features a light-colored sofa and a rich brown leather sofa, both adorned with decorative pillows. A wooden coffee table is placed on a textured area rug, with a backdrop of large windows allowing natural light to fill the space.

4.98 out of 5 average rating, 108 reviews

Starry Night Apt in Va Wine Country

LocationFamilyKitchen

Superhost

A cozy living area features a sectional sofa adorned with bright yellow pillows. A warm blanket is draped over the arm. A large window allows natural light to fill the space, framed by light-colored curtains. A wall art piece depicting autumn trees adds color to the room.

Apartment in Mount Jackson

4.88 out of 5 average rating, 452 reviews

Historic District Apartment with Modern Amenities

FamilyValueParks

4.83 out of 5 average rating, 177 reviews

A spacious wooden porch features two rocking chairs positioned for relaxation. The porch is surrounded by a log railing, with a view of the natural landscape and trees beyond. Sunlight filters through, creating a warm ambiance.

Apartment in Dickerson

Studio apartment at Sugarloaf Log House

LocationFamilyCheck-in

Apartment in Downtown Frederick

4.98 out of 5 average rating, 225 reviews

Carroll Creek Private Apt./Luxury King Bed

LocationValueAccess

Apartment rentals with a hot tub

4.98 out of 5 average rating, 376 reviews

The exterior of Mockingbird Mountain Retreat is shown, featuring a welcoming sign indicating guest parking. The building has a distinctive architecture with a sloped, metal roof and star accent, surrounded by lush greenery.

Apartment in Luray

Mockingbird Spa and retreat *TOP 1% of listings

FamilyLocationCheckout

4.92 out of 5 average rating, 115 reviews

A bright studio space features a spacious bed dressed in striped bedding. Two white chairs with orange cushions are positioned near a large window, allowing ample natural light. A round rug complements the warm flooring, while a modern clock adorns the wall.

Apartment in La Vale

Sweet 68

LocationFamilyAccuracy

Apartment in McGaheysville

A spacious living area features modern seating with two cream-colored armchairs and a coordinating sofa, arranged around a glass coffee table. Natural light enters through large windows, illuminating the wood-patterned flooring and highlighting the decorative wall with stone accents.

4.85 out of 5 average rating, 286 reviews

Massanutten Cozy Condo-Hot Tub&Jacuzzi, EV Charger

FamilyLocationDecor

A view of the serene landscape is captured from the upper level, showcasing a well-maintained lawn leading to a calm river. A row of trees lines the water's edge, while a flag gently waves in the foreground, reflecting the peaceful setting.

4.93 out of 5 average rating, 57 reviews

WV Blue (upper unit)

FamilyLocationDecor

5.0 out of 5 average rating, 26 reviews

A spacious sleeping area features a euro-top king size bed with a light blue striped comforter. A modern light fixture sits atop a decorative nightstand beside the bed. A comfortable grey sofa is positioned against a patterned wall, creating an inviting atmosphere.

Apartment in Mercersburg

Rockwell Suite #201 at the Inns at Whitetail

LocationFamilyWi-Fi