
Apartment holiday rentals in Winchester
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Top-rated apartment rentals in Winchester
Guests agree: these apartments are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Winchester apartment rentals
Weekly apartment rentals

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

Cozy Apartment located on our 5-acre property
Excellent host. Very clean place, beautiful property. Laura was amazing. It was like staying with a good friend. We bought some of her eggs and delicious honey. We would definitely stay there again. My wife and I and our fur babies will miss Laura, Jerald, and Dasher.

Luxury Apt w/ King Bed; Market St Artists' Suite
Just what we wanted. Right in town where we could walk everywhere we wanted to. Mornings were checking up on our horse out away from town, and late afternoon and evening were for wandering around and checking up on everything and then deciding on one of the great places to have dinner. Ava was great for communicating with as needed. Responses were always very quick. Check in and check out we’re really easy! Nice clean place!

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

Blue Haven
Lovettsville is a great area and the location works very well to bounce around between NOVA and Frederick with easy access to Shepherdstown, WV. There is an Anytime Fitness just minutes away as well as a nice coffee shop right down the street. This stay is setup with everything you need from cooking to doing laundry. The hosts were also very helpful!

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
Enjoyed my overnight stay in this charming apartment in a beautiful & quiet rural setting.

Let’s Stay Home
We really enjoyed our stay. The apartment was beautiful and had everything we needed in a very convenient location. The parking situation was a little complicated but everything else was great.
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!

The GreyLoo
Alicia and Philip made check in easy. They both offered recommendations on local places to eat. The property worked out fine for our lodging needs.

Whole Garage Apartment with Blue Ridge Views
This may be our best vacation rental ever! The experience was wonderful. The apartment is spacious and comfortable, with a garage underneath for parking. Cindy provided numerous extra ehancements to facilitate a quality experience. For example, at the outside door, we found laterns, umbrellas, and dog bags. It rained during our stay, but the convenience of having the necessary implements for a late night dog walk, exemplified the special touches Cindy put into her place. Cindy, thank you for the use of your apartment. We loved it, and hope to return in the future.

Mt. Apt. in wine country
Fantastic! Very clean and comfortable. Would absolutely stay there again! Secluded and quiet. Be aware that the very last bit of the road is gravel, so watch out with very low clearance sports cars.

The Corner House-2BR Apt
Susan was wonderful my kids and I loved the place so much we asked to stay 4 months longer and she was very accommodating. Anytime there was any issues with utilities she was quick to update and prompt to give updates again I can't say enough as to how great staying here has been

The Quarters at Belgrove
Our stay was nothing short of amazing. Very responsive and friendly hosts who answered all of our questions promptly. The Airbnb itself was probably the nicest we had ever stayed at. The surrounding grounds were beautiful and filled with wildlife that our young son enjoyed looking at. We have only good things to say about our stay. We would stay again in a heartbeat and highly 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.
Apartment rentals with a hot tub

Berryville Bliss
I booked this home at last minute while visiting Summit point raceway. It appears to be quite new, and everything is super neat and clean. Massive TV and super comfy leather sectional is a great chill space

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.

30 minutes from Washington DC.
the best place what ever seen !!👏👏👏 good job

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.

Riverside Tiny Cabin w Hot Tub, Fire Pit, & Kayaks
Tony’s spot was a great little getaway for a few days of peace and relaxation. Would definitely recommend.

Azul Apt
This place was great! Right on the main strip in town where you can walk to shopping, coffee and food! The host was friendly and helpful to us and the place was so cute! It had just what we needed for the overnight stay for our girls trip! Thank you so much!
Quick stats about flat rentals in Winchester
Total rentals
40 properties
Nightly prices starting at
£23 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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- Luray Caverns
- Whitetail Resort
- Bryce Resort
- Cacapon Resort State Park
- Stone Tower Winery
- Cunningham Falls State Park
- Gambrill State Park
- Robert Trent Jones Golf Club
- South Mountain State Park
- Twin Lakes Golf Course
- Sly Fox Golf Club
- Shenandoah Valley Golf Club
- Bowling Green Country Club
- Whiskey Creek Golf Club
- Berkeley Springs State Park
- River Creek Club
- Creighton Farms
- Notaviva Vineyards
- JayDee's Family Fun Center
- Reston National Golf Course
- Car and Carriage Caravan Museum
- The Golf Club at Lansdowne
- Dinosaur Land
- Herndon Centennial Golf Course