
Apartment vacation rentals in Winchester
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Top-rated apartment rentals in Winchester
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Popular amenities for Winchester apartment rentals
Weekly apartment rentals

Best Location - Full Apartment
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!

Apt near i81/hiking/wineries
This place is a great gateway to the mountains. The apartment is well-equipped and comfortable, and I’ll definitely be staying there again.

Easy like a Sunday Morning 1 BR apt great location
Kim's communication was good. The Place is in a very old building, but was fine for overnight.

Boxcar Studio at The Depot - Shenandoah
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!!

The Flat of Old Town Winchester
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.

The Speakeasy Listening Room
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 ☺️

"Cozy on Cameron!" - Historic Downtown Winchester
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.

Cozy room
My host was very friendly and responsive. The place was also cozy and clean.
Private apartment rentals

Whole Garage Apartment with Blue Ridge Views
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 !

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

The Downtown Flat at Creekside
great digs close to mineral baths and restaurants.

Newtown Cozy Cottage Basement
I enjoyed my stay. Very convenient to nearby restaurants and shopping. I would recommend this place to others.

Historic unit- 6 mi to Shenandoah Cavern
Andrea was very kind and her place was beautiful and clean. Instructions were perfect. Everything matched the description.

Red Fox Retreat
Repeat customer! Great place to stay & a very convenient location. Thank you.

Spacious Charming Basement Apt
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.

DMV 2BR LakeFront Apt - Firepit
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

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!

Massanutten Cozy Condo with Hot Tub & Jacuzzi
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 !

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
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!

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

West Virginia Blue (upper unit)
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.

Country calm and close to city
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!

The Parlor Suite
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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- Luray Caverns
- Cunningham Falls State Park
- Stone Tower Winery
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Bryce Resort
- Whiskey Creek Golf Club
- Gambrill State Park
- Whitetail Resort
- South Mountain State Park
- Sly Fox Golf Club
- Creighton Farms
- Shenandoah Valley Golf Club
- Bowling Green Country Club
- Notaviva Vineyards
- Twin Lakes Golf Course
- Berkeley Springs State Park
- River Creek Club
- JayDee's Family Fun Center
- Reston National Golf Course
- Car and Carriage Caravan Museum
- Warden Lake
- The Golf Club at Lansdowne
- Dinosaur Land