Apartment vacation rentals in Winchester

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Popular amenities for Winchester apartment rentals

Weekly apartment rentals

Superhost
A spacious game area features a billiard table with balls arranged for a game. Soft blue lighting creates an ambient atmosphere, while a large screen is visible in the background, indicating a space suitable for entertainment and leisure.
Apartment in Woodbridge
4.67 out of 5 average rating, 86 reviews

2 Bedroom Basement Apartment with Kitchenette

AbigailRating, 5 stars3 months ago
Great place to stay for a few nights near dc! Host was responsive and helpful whenever I needed to reach out. Airbnb is in a great area with plenty of food options nearby
Guest favorite
An exterior view of the studio apartment showcases a white siding entrance with a glass door. Nearby, a small garden area features neatly trimmed plants and a brick planter, complemented by a clear blue sky.
Apartment in Frederick
4.91 out of 5 average rating, 162 reviews

Your own "Tiny House"

ChristianRating, 5 stars1 month ago
Becky was wonderful from start to finish awesome little place to stay very clean and the area was beautiful thank you Becky for everything I will definitely be back!
Top guest favorite
The living area is illuminated by natural light from multiple large windows. A black leather sectional couch and a small round table are placed on a patterned area rug, with a view of the kitchen in the background featuring dark cabinetry and modern appliances.
Apartment in Downtown Frederick
4.98 out of 5 average rating, 136 reviews

Luxury Apt w/ King Bed; Market St Artists' Suite

GizethRating, 5 stars1 month ago
Ava was so pleasant and helpful. The space was cozy and had everything we needed and more! Would definitely recommend.
Superhost
The spacious kitchen is equipped with modern appliances, including a stainless steel refrigerator and gas stove. Ample wooden cabinetry offers storage, while a large island with bar seating provides a casual dining area. Natural light enters from a window, enhancing the inviting atmosphere.
Apartment in Waynesboro
4.69 out of 5 average rating, 26 reviews

Apt A, 3 bedrooms, Waynesboro, PA

DameyonRating, 5 stars6 months ago
Great host comfortable home.
Superhost
A cozy living area features a fireplace flanked by built-in shelves with books. Two rocking chairs are positioned near a wooden coffee table, which has a decorative centerpiece. A framed elephant print is displayed on the wall, complementing the neutral tones of the space.
Apartment in Chantilly
4.9 out of 5 average rating, 41 reviews

Out of Africa

JamesRating, 5 stars8 months ago
This is my second review of the apartment and it couldn’t be more perfect for a short or long-term stay. Mary Kay and Brad are great hosts and quickly communicate for any question or need. The apartment has a nice separate layout with a comfortable bedroom, cozy living room and well-equipped kitchen. If I’m ever in the Northern Virginia area again I’ll happily stay here. Jim
Top guest favorite
A cozy seating area features a soft, neutral sofa adorned with decorative pillows. A patchwork quilt hangs on the wall, complementing a rustic coffee table. Candles and magazines sit atop the table, and light is provided by a nearby lamp.
Apartment in Marshall
4.94 out of 5 average rating, 116 reviews

The Lodge at Turkey Creek

TinaRating, 5 stars1 week ago
We absolutely loved our five night stay with Renee. Our apartment was perfect for us (with our dog) and is decorated beautifully. Renee was very attentive and so personable! We had everything that we needed. The property was lovely and so peaceful. The Airbnb is only 6 miles from the town of Marshall and the 6 mile drive is quite scenic. The location was centrally located for easy access to restaurants, state parks, vineyards etc. We enjoyed our stay so much that we have already booked another stay.
Guest favorite
The studio apartment showcases a compact layout with a modern kitchenette equipped with stainless steel appliances. A cozy sleeping area features a spacious bed adorned with soft linens. A wooden dining table with black stools is positioned nearby, creating a welcoming space for dining.
Apartment in Downtown Frederick
4.89 out of 5 average rating, 307 reviews

Downtown Frederick Modern Studio

BeataRating, 5 stars1 month ago
I stayed with Allison and Josh multiple times and they never disappoint. I'll keep coming back! :)
Guest favorite
A cozy loft area is highlighted by a plush chaise lounge positioned near a wooden railing. A small side table stands beside the lounge. Soft green carpet covers the floor, and natural light filters in from a window, creating a warm and inviting space.
Apartment in Midlothian
4.82 out of 5 average rating, 39 reviews

Unique 1BR Tri-level Apartment near FSU.

TomRating, 5 stars2 months ago
Very cool kitschy place just a short drive away from the main drag. Nice and cozy layout, comfortable bed, and great tub for soaking.

Private apartment rentals

Top guest favorite
A large two-story home is bordered by a white picket fence and features a blue metal roof. A front porch with railings is visible, along with well-maintained landscaping and trees in the background. Clear blue skies complement the peaceful rural setting.
Apartment in Blue Ridge Summit
5 out of 5 average rating, 17 reviews

Mountain Top Suite Central location from MD/PA/WVA

JeffreyRating, 5 stars1 week ago
We had a wonderful stay with Mike & Jodi...they are extremely kind and gracious hosts. The space is amazing...much larger than it looks in the pictures. The furniture and bedding is new and very comfortable. The neighborhood is very safe and an excellent location close to Waynesburg, Emmitsburg, Gettysburg and Liberty Ski Resort. Highly recommended!
Top guest favorite
A spacious living area features a cozy sectional sofa and an ottoman, with a large wall-mounted TV providing a central focus. The walls are painted in a calming blue, complemented by framed artwork and clocks, while the nearby kitchen is visible through an open entrance.
Apartment in Manassas
4.99 out of 5 average rating, 150 reviews

Manassas Luxe Stay - Aviation-Themed Modern Escape

RachelRating, 5 stars2 weeks ago
Awesome place, very unique and creative. The hosts were so friendly and frequently checked in to see if I needed anything. Very clean. Comfy bed! All around great
Guest favorite
A welcoming entrance sign for Goose Hill stands beside vibrant pink and green landscaping. Lush foliage is complemented by flowering trees, creating a tranquil setting. Sunlight filters through the branches, enhancing the natural beauty of the surroundings.
Apartment in Hamilton
4.97 out of 5 average rating, 60 reviews

Goose Hill

JesseRating, 5 stars5 months ago
The place was charming, well stocked and very comfortable. The communication was great and we would definitely rent again.
Superhost
A welcoming living area displays a large sectional sofa and a comfortable armchair, paired with a marble coffee table. Natural light filters through multiple windows and a modern fireplace is situated below a mounted television, enhancing the overall atmosphere.
Apartment in Frederick
4.87 out of 5 average rating, 15 reviews

Luxury Basement Apartment Suite

AlexRating, 5 stars9 months ago
Stay was exactly as described. Home was clean and had everything needed for a home base for work and camp for the kids. Jorge and John we very communicative and friendly. 100% would reccomend.
Top guest favorite
A bright living area features a comfortable gray sofa and two armchairs. An entertainment unit holds a television, while a coffee table with a small plant sits in the center. Colorful artwork adorns the walls, and natural light enters through large windows.
Apartment in Leesburg
4.99 out of 5 average rating, 190 reviews

The Quarters at Belgrove

LauraRating, 5 stars2 weeks ago
We stayed here for the weekend and got engaged so I might be a little biased, but it is absolutely beautiful. The place was clean and sooo well updated. The countertops specifically were something that makes you want to go home and redo your own kitchen. There was champagne waiting in the fridge and I’m embarrassed to say we ate almost all of the plentiful snack provided. I don’t even think the pictures do the ground justice. You sit out on the deck overlooking fields with horses. The mini horses were even better than expected. They were sooo friendly and run right up to you looking for pets and treats. A man came over and gave my treats to feed them which they took very happily. At the end of the trip we not only said we’d like to come back again, but would like to make it an annual trip. Definitely would recommend.
Guest favorite
An open living area features high-beamed ceilings adorned with wooden panels. A spacious sectional sofa is paired with a round dining table. Modern kitchen appliances are arranged within white cabinetry, and a cozy electric fireplace adds warmth to the space.
Apartment in Harrisonburg
4.92 out of 5 average rating, 39 reviews

Private, Pet-Friendly Apartment

JewelRating, 5 stars1 month ago
Beautiful home, super cozy, and clean! Amazing views. Absolutely loved spending time with your cute dogs & cat. Thank you for your quick responses and accommodating our last minute stay!
Top guest favorite
A spacious living area features a large red area rug at the center, surrounded by comfortable seating. An open kitchen, equipped with wooden cabinetry and modern appliances, is visible in the background, enhancing the warm and functional space. Natural light streams in through the windows.
Apartment in Centreville
4.76 out of 5 average rating, 51 reviews

Luxurious Guest Apartment with Steam Room Shower

SooRating, 5 stars4 months ago
David & Lynn are wonderful hosts! My plans had changed, and I was happy to book their place again. It was one of the few bookings that felt like home. Thank you both very much for hosting me for my second stay. The In-Law Suite is great. Everything you need is there. My only recommendation is to have your own network cable to connect to the router if you are particular about the cable type and speed.
Guest favorite
A well-lit kitchen area features bright yellow walls and a spacious island with seating. The kitchen appliances include a refrigerator and oven, and a window seating area is adorned with cushions. Large windows allow natural light to fill the space, complemented by decorative plants.
Apartment in Warrenton
4.95 out of 5 average rating, 266 reviews

Entire Spacious Apartment with Private Entrance

MatthewRating, 5 stars2 weeks ago
Carl's place was spacious, clean, and well-appointed - exactly as described, and perfect for my short visit. Thanks!

Apartment rentals with a hot tub

Guest favorite
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 stars9 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!
Guest favorite
A cozy living room is presented, featuring a stone accent wall and a flat-screen TV mounted above a heater. Comfortable seating includes a gray sofa and a recliner. A simple coffee table is positioned on a textured rug, with natural light illuminating the space through a nearby window.
Apartment in Shepherdstown
4.95 out of 5 average rating, 20 reviews

West Virginia Gold (lower unit)

MikeRating, 5 stars6 days ago
A friend & I stayed to cycle & hike Harper's Ferry & the Shepardstown area of the C&O. The placed checked all our important boxes..very clean, nice shower with hot water, very comfortable beds & furniture, very quiet, strong wifi. Download Google maps directions to get there as you might loose your cell connection. Same if you travel the area..download while on wifi at the house. When I saw the vintage GE electric stove with push button controls I though...wow will this thing work! Yes it works great! It heated up my hot water for tea & oatmeal faster than any modern stove! We had a great stay and will definitely stay again.
Top guest favorite
A comfortable sitting area is highlighted by a light gray leather sofa, complemented by a glass coffee table. A wooden entertainment unit houses a television and shelves filled with books. Accent lighting illuminates the space, while a doorway leads to another room.
Apartment in Harpers Ferry
4.95 out of 5 average rating, 137 reviews

Harpers Ferry Apartment w/ Private Pool & Hot Tub!

GisellRating, 5 stars1 month ago
The location was perfect and so was everything else. We really enjoyed our stay and look forward to coming back.
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 weeks 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
4.97 out of 5 average rating, 119 reviews

Yoder School Guest House with wifi and hot tub

MeaghanRating, 5 stars2 weeks ago
Rhoda’s listing was absolutely perfect! Very relaxing surroundings, private, and serene! The amenities were super helpful, too! Definitely recommend stopping by here!
Superhost
A cozy sitting area is presented with floral wallpaper, featuring two wooden chairs with green cushions around a small table. Natural light filters through two white-draped windows, illuminating a vintage dresser and a mirror on the wall.
Apartment in Berkeley Springs
4.78 out of 5 average rating, 87 reviews

The Parlor Suite

BradleyRating, 5 stars2 weeks ago
Excellent stay in a nice part of town
Guest favorite
A cozy living area features a spacious sectional sofa adorned with accent pillows. A glass coffee table sits on a woven rug, surrounded by natural light from large windows. A stylish chandelier and nature-themed artwork enhance the serene atmosphere, complemented by dark curtains.
Apartment in Nokesville
4.96 out of 5 average rating, 23 reviews

Country calm and close to city

LiamRating, 5 stars5 days ago
This Airbnb was the perfect escape from the hustle and bustle of the city! If you’re looking for a place to reconnect with nature and truly unwind, this is it. The apartment was spacious, well-equipped, and had everything we needed for a relaxing weekend. The sunsets were absolutely breathtaking, and waking up to the sight of horses each morning was a magical bonus. I would highly recommend this Airbnb to anyone seeking a peaceful, nature-filled retreat!
Guest favorite
A hot tub is featured in an outdoor setting, surrounded by pebble stones and planters with lush greenery. A set of wooden steps leads up to the tub, which is filled with bubbling water. The background includes an outbuilding and tree-covered hills.
Apartment in La Vale
4.89 out of 5 average rating, 66 reviews

Sweet 68

TrevorRating, 5 stars5 days ago
For my first time being there was really really nice. I love the small town. Never had to worry about anything. It was really nice. She was a very good host. I have nothing bad to say.

Quick stats about apartment rentals in Winchester

  • Total rentals

    40 properties

  • Nightly prices starting at

    $30 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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