Apartment vacation rentals in Winchester

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Popular amenities for Winchester apartment rentals

Weekly apartment rentals

Guest favorite
A cozy living area features a gray sectional sofa and an armchair, complemented by a glass coffee table. Natural light filters through the window, illuminating the space. A potted plant adds a touch of greenery, while artwork adorns the walls, providing visual interest.
Apartment in Downtown Frederick
4.95 out of 5 average rating, 102 reviews

Best Location - Full Apartment

EmilyRating, 5 stars1 week ago
We had a great stay at Marc's place. His directions were really helpful, the place was spacious and clean, and the location was perfect for walking to shops, restaurants, and the local art shows on Carroll Creek. I especially liked how Marc had the AC running upon our arrival on a hot day and how comfortable the bed was - an important feature after a long art show day. Thanks, Marc!
Guest favorite
A bright bedroom features a spacious bed adorned with a patterned quilt. Two large windows are dressed with light curtains, allowing natural light to fill the room. Floral artwork hangs above the bed, complemented by a nightstand and a simple area rug on the hardwood floor.
Apartment in Woodstock
4.91 out of 5 average rating, 33 reviews

Apt near i81/hiking/wineries

ChiquimaRating, 5 stars3 weeks ago
This place is a great gateway to the mountains. The apartment is well-equipped and comfortable, and I’ll definitely be staying there again.
Guest favorite
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.
Apartment in Winchester
4.95 out of 5 average rating, 77 reviews

Easy like a Sunday Morning 1 BR apt great location

VirginiaRating, 5 stars1 week ago
Kim's communication was good. The Place is in a very old building, but was fine for overnight.
Superhost
A well-appointed sleeping area features a queen-size sleigh bed adorned with soft bedding. A cozy pull-out sofa is positioned in the corner, with a wood dresser nearby. The space is complemented by warm overhead lighting and an open view toward a galley kitchen area.
Apartment in Shenandoah
4.87 out of 5 average rating, 103 reviews

Boxcar Studio at The Depot - Shenandoah

AlexisRating, 5 stars2 weeks ago
This place was so cute! Everything was clean and clearly taken care of. Plenty of space to park and had the most gorgeous view with benches all along the street. The railroad station is across the road but I heard no noise from the trains during our whole stay. The area is in the middle of plenty things to do from river put ins, skyline drive, great restaurants, sightseeing, and many other things. The hosts have everything set up to be very welcoming! I HIGHLY recommend!!
Superhost
A spacious bedroom is highlighted by large bay windows with blue curtains. A dark wood bed frames a neatly made bed, complemented by a decorative table and elegant furniture pieces. A ceiling fan is mounted above, providing a comfortable ambiance.
Apartment in Winchester
4.69 out of 5 average rating, 36 reviews

The Flat of Old Town Winchester

TheresaRating, 5 stars2 weeks ago
The room was just as pictured and described. It was easy to find. The directions were clear. The room had a guest binder that made it easy to find a restaurant and I even enjoyed reading through the town history book. When we drove around town I pointed out buildings I had just learned about! There are motion activated lights in the hallways that I thought were a great touch! I loved the designated parking in the back.
Guest favorite
A spacious bedroom features wooden beams above and warm lighting. A large bed with a striped coverlet is positioned in the center, while guitars and wall art adorn the light-colored walls. A comfortable chair is located next to sliding glass doors leading outside.
Apartment in Martinsburg
4.94 out of 5 average rating, 49 reviews

The Speakeasy Listening Room

AdiaRating, 5 stars1 month ago
We have stayed at Lesley’s properties before, and they never fail to impress! This was the perfect place to take our relaxing getaway. We did not explore Martinsburg too much, but instead used it as a midway point between Berkeley Springs and Harper’s Ferry. The bed was super cozy, I enjoyed playing the piano, and the tub is beautiful! We would definitely stay here again ☺️
Superhost
A modern living area features a gray tufted sofa complemented by decorative pillows. Two vibrant abstract artworks hang on the white walls. A glass dining table with four chairs is positioned nearby, with warm wood flooring enhancing the inviting atmosphere of the space.
Apartment in Winchester
4.77 out of 5 average rating, 13 reviews

"Cozy on Cameron!" - Historic Downtown Winchester

MatthiasRating, 5 stars6 months ago
Marks place is a delight in the heart of winchester, we're happy having been lucky enough to have it available at the dates we needed. It's a few walking minutes from the Old town center of winchester. The place is lovely and has all you'll need even for a few weeks stay. A private parking on top of that is just so nice to have. We'll definitely check in again the next time we're in winchester.
Guest favorite
A cozy sleeping area features a spacious bed with white linens and a decorative green pillow. A piece of wall art depicting trees hangs above the headboard. Bedside tables with lamps add functionality, while soft light creates a serene atmosphere.
Apartment in Ashburn
4.95 out of 5 average rating, 352 reviews

Cozy room

NancyRating, 5 stars2 weeks ago
My host was very friendly and responsive. The place was also cozy and clean.

Private apartment rentals

Top guest favorite
The exterior of a charming white farmhouse is seen, featuring a steep roof, multiple gabled dormers, and a weather vane atop the structure. A circular driveway leads to the garage bays below, surrounded by lush greenery and under a wide, partly cloudy sky.
Apartment in Round Hill Village
5 out of 5 average rating, 67 reviews

Whole Garage Apartment with Blue Ridge Views

DianaRating, 5 stars2 weeks ago
Our second stay here. Just as good as the first. We met our family most every day (15 minutes away) and got to participate in their many activities, and yet have a quiet, clean, large space to retreat to. They were so flexible that we felt like family !
Top guest favorite
A cozy living area is depicted, featuring two gray sofas adorned with yellow and orange throw pillows. A dining table with four chairs is situated beside a window, along with a decorative plant. A ceiling fan adds an element of comfort to the space.
Apartment in Front Royal
5 out of 5 average rating, 28 reviews

Woodpecker: NEW~Cozy~Downtown~Main S~National Park

JoshRating, 5 stars1 week ago
we had a wonderful long weekend golf getaway! This place is in a super cool location! Lots of golf within a 20-30 min radius. Tons of neat little shops and stuff to see within walking distance. The town is very clean and the people were super friendly. I would highly recommend staying here if you are in the area! We will be back!!!
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, 67 reviews

The Downtown Flat at Creekside

ErnestRating, 5 stars3 days ago
great digs close to mineral baths and restaurants.
Superhost
A cozy sitting area is illustrated with two floral paintings on light green walls. A beige sofa is adorned with colorful pillows in shades of orange and green. A sleek black lamp is positioned beside the sofa, providing focused lighting, while a small table holds decorative items.
Apartment in Stephens City
4.86 out of 5 average rating, 7 reviews

Newtown Cozy Cottage Basement

SandraRating, 5 stars3 weeks ago
I enjoyed my stay. Very convenient to nearby restaurants and shopping. I would recommend this place to others.
Guest favorite
A cozy living room features warm wooden flooring and soft gray walls. A flat-screen TV is placed atop a vintage gray dresser, surrounded by plants. A rocking chair and a small accent table enhance the inviting atmosphere, with natural light filtering through sheer curtains.
Apartment in New Market
4.94 out of 5 average rating, 48 reviews

Historic unit- 6 mi to Shenandoah Cavern

CleonicaRating, 5 stars6 days ago
Andrea was very kind and her place was beautiful and clean. Instructions were perfect. Everything matched the description.
Top guest favorite
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
4.98 out of 5 average rating, 99 reviews

Red Fox Retreat

John RRating, 5 stars1 week ago
Repeat customer! Great place to stay & a very convenient location. Thank you.
Top guest favorite
A cozy living area features a red sofa adorned with decorative pillows, facing a wooden media console with a television. A round coffee table sits centrally on a patterned rug. Two lamps provide soft lighting, creating an inviting space for relaxation.
Apartment in Stephens City
5 out of 5 average rating, 16 reviews

Spacious Charming Basement Apt

John and AlexisRating, 5 stars3 months ago
Great place to stay while visiting Stephens City, VA. The basement was spotless and we immediately noticed that it had been recently cleaned; fresh and airy. This location is easily walkable to the historic city center where you will find antique shops and restaurants. We contacted the hosts during our stay and they were very responsive to our questions. This would be an ideal location for a long-term stay.
Top guest favorite
A neutral-toned living room is highlighted by soft lighting and modern furnishings. A cozy sofa with throw blankets is paired with a wooden chair. A beige area rug anchors the space, complemented by a simple coffee table. Artwork adorns the walls, enhancing the contemporary aesthetic.
Apartment in Gaithersburg
5 out of 5 average rating, 15 reviews

DMV 2BR LakeFront Apt - Firepit

AmyRating, 5 stars1 month ago
Absolutely beautiful location. Incredibly peaceful and quiet being so close to so many attractions and amenities. The apartment was bright, spacious, and private.

Apartment rentals with a hot tub

Superhost
A bright living area is presented, featuring a large sectional sofa adorned with decorative pillows. A glass coffee table sits centrally, complemented by a blue accent chair. A flat-screen television is mounted on a sleek stand, while soft light filters through the window covered by sheer curtains.
Apartment in Woodbridge
4.95 out of 5 average rating, 58 reviews

Getaway | Hidden Gem | Free-Parking

ValerieRating, 5 stars10 months ago
TODD’S is KING! We have been searching for our new home & have stayed in 2 of their buildings. TODDs’ customer service has been fast, reliable & friendly! TODD’s has made us feel relaxed & welcomed during our visits. Our cat feels at home here, too! He has been anxious in other Abnbs, so it’s a great benefit. Their units are clean & stocked with essentials — like bathroom, laundry & kitchen supplies. The bed is super comfy as is the living room couch. The TV is large & U can stream your favorite channels. They even supply a safe — for your valuables — and an ironing board & iron for that quick press! A big closet, too! We have very much appreciated TODD’S staff for many reasons. They WANT to help & they WANT their guests happy. They went out of their way to help us elongate our stay, when we realized we needed more time! They kindly juggled other reservations to ensure we could stay longer. Such a pleasant surprise & experience! We recommend TODD’s highly!
Superhost
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.
Apartment in McGaheysville
4.84 out of 5 average rating, 255 reviews

Massanutten Cozy Condo with Hot Tub & Jacuzzi

PhilipRating, 5 stars1 month ago
We arrived late after an evening graduation. Easy self check in. Welcome package was a nice touch. The place was equipped with what was needed for a enjoyable stay. We had a car issue and owner messege me with solutions. Fortunately our family picked us up and we were able to continue celebrating. Was able to charge battery with her charger and extension cord. Maya assistance kept the graduation celebrations the focus. Much appreciated !
Top guest favorite
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
5 out of 5 average rating, 20 reviews

Rockwell Suite #201 at the Inns at Whitetail

EricRating, 5 stars2 months ago
Absolutely beautiful views of the hills. It was 70 degrees during my stay, but the ski-on feature 50 feet from the front door led to some nice hikes up the mountain during off-season. Charlie offered me early check-in and late check-out which—in my experience—is pretty rare and generous on AirBnB. The space felt actually bigger than the photos portrayed. I’d love to stay again.
Top guest favorite
A well-appointed kitchen features warm wood cabinetry and a spacious granite countertop. Stainless steel appliances, including a gas range and microwave, are visible. A central island provides additional preparation space, with overhead lighting illuminating the area. Natural light enters from the adjacent room.
Apartment in Grantsville
4.98 out of 5 average rating, 124 reviews

Yoder School Guest House with wifi and hot tub

LauraRating, 5 stars3 weeks ago
We had a wonderful stay at the Yoder School House. It was so peaceful and relaxing, especially the hot tub with a lovely view of the farmland and watching all the birds at the feeder and in the field over coffee in the mornings. The house had everything we could need - Rhoda is very thoughtful in stocking the kitchen and even leaving fun board games. We loved the proximity to the Casselman Creamery, and it was a great location for day trips to hike Mount Davis and explore Ohiopyle State Park in PA. WE would definitely stay here again! Highly recommend!
A modern tiny cabin is nestled among trees, featuring a spacious deck with seating and a fire pit surrounded by blue Adirondack chairs. Large windows allow natural light to fill the interior, while stone landscaping enhances the outdoor setting.
Apartment in Rileyville
4.81 out of 5 average rating, 186 reviews

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

TaylorRating, 5 stars2 weeks ago
Great stay along the river! Even though there are other cabins around, still felt very private. Hot tub was excellent! Very thorough instructions and communication
Guest favorite
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.
Apartment in Shepherdstown
4.91 out of 5 average rating, 23 reviews

West Virginia Blue (upper unit)

JenniferRating, 5 stars4 days ago
Clean, quiet, nice view of the river, especially when you're enjoying it from the hot tub. The two floors are rented out separately, so it's a bit less private when someone is renting the other floor, but it'd be a great option for two groups traveling together. The Florida room is really more of a hallway, but we did enjoy sitting out there and playing games (there's a good variety available) on a rainy day.
Guest favorite
A spacious living area features a large sectional sofa, complemented by a decorative throw and cushions. Natural light filters through the two windows with dark curtains. A wooden coffee table rests on a textured area rug, while a stylish chandelier hangs from the ceiling.
Apartment in Nokesville
4.89 out of 5 average rating, 27 reviews

Country calm and close to city

LincolnRating, 5 stars1 month ago
Awesome place to stay if you’re looking to get away from the city or have a quiet weekend away. The place was very clean and cute. We also enjoyed watching the animals. loved this place!
Superhost
A spacious room features a vintage metal bedframe with light bedding, surrounded by floral wallpaper. Natural light filters through multiple windows, illuminating the hardwood floor. A cozy seating area with wooden chairs and a small table is situated next to a decorative fireplace.
Apartment in Berkeley Springs
4.77 out of 5 average rating, 94 reviews

The Parlor Suite

MonaRating, 5 stars2 weeks ago
My friend and I had such a wonderful stay at this beautiful decorated house! The location couldn’t be better—just steps from the center of town and close to all the local shops, restaurants, and activities. The home itself is full of charm and thoughtful touches, with plenty of natural light throughout. One of the highlights for me was the whirlpool bathtub—perfect for unwinding after a day of exploring. The bed was incredibly comfortable, and I loved waking up in the sunlit bedroom feeling totally refreshed. Highly recommend this gem of a place!

Quick stats about apartment rentals in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    ﺩ.ﺇ110 before taxes and fees

  • Total number of reviews

    3.6K reviews

  • Family-friendly rentals

    10 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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