
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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Winchester apartment rentals
Weekly apartment rentals

2 Bedroom Basement Apartment with Kitchenette
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

Your own "Tiny House"
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!

Luxury Apt w/ King Bed; Market St Artists' Suite
Ava was so pleasant and helpful. The space was cozy and had everything we needed and more! Would definitely recommend.

Apt A, 3 bedrooms, Waynesboro, PA
Great host comfortable home.

Out of Africa
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

The Lodge at Turkey Creek
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.

Downtown Frederick Modern Studio
I stayed with Allison and Josh multiple times and they never disappoint. I'll keep coming back! :)

Unique 1BR Tri-level Apartment near FSU.
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

Mountain Top Suite Central location from MD/PA/WVA
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!

Manassas Luxe Stay - Aviation-Themed Modern Escape
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

Goose Hill
The place was charming, well stocked and very comfortable. The communication was great and we would definitely rent again.

Luxury Basement Apartment Suite
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.

The Quarters at Belgrove
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.

Private, Pet-Friendly Apartment
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!

Luxurious Guest Apartment with Steam Room Shower
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.

Entire Spacious Apartment with Private Entrance
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

Getaway | Hidden Gem | Free-Parking
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!

West Virginia Gold (lower unit)
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.

Harpers Ferry Apartment w/ Private Pool & Hot Tub!
The location was perfect and so was everything else. We really enjoyed our stay and look forward to coming back.

Rockwell Suite #201 at the Inns at Whitetail
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.

Yoder School Guest House with wifi and hot tub
Rhoda’s listing was absolutely perfect! Very relaxing surroundings, private, and serene! The amenities were super helpful, too! Definitely recommend stopping by here!

The Parlor Suite
Excellent stay in a nice part of town

Country calm and close to city
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!

Sweet 68
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
Destinations to explore
- Rappahannock River Vacation rentals
- Outer Banks Vacation rentals
- Washington Vacation rentals
- Philadelphia Vacation rentals
- Pocono Mountains Vacation rentals
- South Jersey Vacation rentals
- Jersey Shore Vacation rentals
- New York Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Plainview Vacation rentals
- Long Island Vacation rentals
- Family-friendly rentals Winchester
- Cottage rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a washer and dryer Winchester
- Condo rentals Winchester
- Cabin rentals Winchester
- Rentals with a patio Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Apartment rentals Virginia
- Apartment rentals United States
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Bryce Resort
- Luray Caverns
- Whitetail Resort
- Cacapon Resort State Park
- Stone Tower Winery
- Gambrill State Park
- Cunningham Falls State Park
- South Mountain State Park
- Robert Trent Jones Golf Club
- Twin Lakes Golf Course
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Whiskey Creek Golf Club
- Sly Fox Golf Club
- Bowling Green Country Club
- Creighton Farms
- Berkeley Springs State Park
- JayDee's Family Fun Center
- River Creek Club
- Reston National Golf Course
- Car and Carriage Caravan Museum
- Dinosaur Land
- The Golf Club at Lansdowne
- Herndon Centennial Golf Course
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes