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

Modern Condo In Downtown Frederick
Spacious “condo” really the entire lower floor of a restored older home Fantastic location - easy walk to the restaurants and shops in the historic district

Memory Lane
This AirBnb hosted by Julie was perfect! The space was just what we needed as a little home base as we explored Harper’s Ferry and the surrounding area. Julie provided great recommendations in terms of places to eat. Would love to go back!

Upscale Walkup Apartment
Nice, clean place. Good location for that area.

Private 2/2 full baths very bright basement home
We had a lovely stay at Lili's place. It was very peaceful! We would definitely book again if we were in the area. Lili was very responsive to any questions we had.

Cozy King Bed Suite With A Kitchen & ClawfootTub
I was born and raised in Cumberland and have always been familiar with Washington St. Probably the single most beautiful street in Cumberland. Love did an amazing job describing the building and all the amenities and local attractions. We would definitely stay there again. What a beautiful building. Thanks so very much for sharing your home with us. Alan

Condo at Bryce Resort
I wish I could have stayed longer to enjoy this condo and more of the area. Beautiful and peaceful place to relax, enjoyed a couple of wineries but didn’t try the restaurants. I don’t ski but I’d love to watch the skiers in wintertime because it’s a great view of the slopes. Next time I’ll play golf and check out the restaurants in the area

2 Bed Condo at Abolitionist Ale Works #300
Second time I have stayed and I enjoy the location and the close by food and drink options. Very quiet for a downtown location. While they do not offer parking, free parking is just two blocks away. The street parking in from of Abolitionist makes it easy to unload.

Massanutten Summit 2BR, 2BA
My family and I definitely enjoyed our stay. This was our 5 year anniversary Christmas at massunutten and the location did not disappoint anyone. We enjoyed being on the mountain watching the skiers go up and come down the slopes. The kids enjoyed being close to all the snow activities. We are looking forward to rebooking and going back during the summer once all the new add-ons are done. Thank you Daniel
Pet-friendly apartment rentals

Ski/MTB/Golf Condo (#122) - Mountain views!
Great location for riding. Our stay was great

Ski🎿 & hike from front steps—Mountainside getaway
I think this is the best slope side ski condo at Whitetail. The slopes are right outside the door and the place is cute, clean, and comfortable. We will be going back!

1 Bed/1 Bath/1Pkg Space|Dogs-OK
Yue’s place is great and especially quiet. It is conveniently located near grocery, pharmacy, and banks. The most attractive though is a lake close by that is great for walks. Everything worked well and Yue was very responsive- always asking if there is more she can do. I will definitely come back again. One caution is the flight of stairs so if you are elderly or have a bad knee, that might be a problem.

Whitetail Resort Ski-in/Ski-out slope side condo.
This air bnb was perfect for a weekend getaway to Whitetail resort. The unit is steps away from the slopes, and Renee was not only responsive and extremely helpful, but able to accommodate schedule changes to make our trip happen.

Bike,Hike,Relax in Lux! at Bryce Resort
This place is fantastic. It's comfortable in every way, charming, beautifully decorated, spacious, and spotlessly clean. It's even nicer than the photos suggest. The location right at the base of the slopes at Bryce is perfect. I'll definitely stay here again someday!

Lark's Nest on Market
We very much enjoyed our stay and appreciated being able to bring our dog. It’s a great layout, well decorated, and the deck has a terrific view of the sunsets. Easy walking distance to the restaurants and Baker Park. We will be glad to return.

Perfect Location Old town / walk to the metro
This was my first Airbnb experience and it was exceptional! The host communicated very well and was very responsive. The condo was very clean and the location was great as it was super close to great restaurants and local shops. I would definitely rent again!

Mountain View’s, pet friendly, walk to Lake Laura
This was exactly what my husband and I needed to get out of the busy shuffle of the cities. Peaceful. Great breweries nearby! The house was very clean, but still had that cabin feel. Porch was a great place to sit and drink coffee or hang out with beautiful views.
Apartment rentals with a pool

Redwood 2 Condo Graves Mountain Farm in Blue Ridge
We wanted a quiet place away to enjoy nature. This was perfect. A few miles from great waterfall hiking…white Oak Canyon in SNP. We enjoy birding and found there was a great variety of birds to be heard. The leaves were pretty full on the trees, so viewing them was the challenge. We enjoyed the deck for birding right at the rental! We had three couples, a fourth invited but unable to come, so every couple had their own space. We prepared all our food, and the kitchen had a lot of space, and modestly stocked with utensils, etc. Being older our caloric needs were not much, so we did not feel we could eat our moneys worth at the restaurant. We really enjoyed the live music in the serene setting on Fri eve. We enjoyed watching the storm pass through Sat eve and the rainbow that formed.

Summit Hillside at Massanutten
Stayed here for a weekend getaway and loved every minute. Beautiful location, comfy beds, excellent bathtub. Make sure to spend some time sitting on the covered porch off the living room.

The Music Room at Ski Whitetail!
This studio apartment-room was a great stay! It was the closest building to the top of the Double lift, 8-10 minutes from line to the apt door. Everything was as described for me, sans a guitar and a table or two. The wifi was fine for work, not great for gaming on my pc, though. Overall, my pet and I enjoyed every second of our 2+ weeks, on and off the slopes (just me), and look forward to staying again. Thanks!

Eagle Trace Condo at Massanutten 1br/1ba hottub
We had a great time at Ann’s place! She was very communicative and easy/quick to reach whenever we had a question. The place was was so comfortable and we really enjoyed relaxing in the jacuzzi after our long days on the slopes. Would definitely recommend!

Massanutten Woodstone 1 Bedroom Standard Condo
Great little weekend getaway! The one bedroom Condo with partial kitchen was perfect! Tons of activities to do around the resort! We will return!

Luxury 2BR 2BA w Hot Tub bath at Massanutten
Great place and responsive host.

The Fountains condo one bedroom 2 level apartment
The host was more than accommodating and the condo Is exactly as pictured . Great stay

Aspen East 313/314 -- SKI-IN/SKI-OUT!
The place was dated (as noted) but also roomy and cozy. You certainly can’t beat the price and location for skiing. Solid value I’d say.
Destinations to explore
- Rappahannock River Holiday rentals
- Outer Banks Holiday rentals
- Washington Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- South Jersey Holiday rentals
- Jersey Shore Holiday rentals
- New York Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Plainview Holiday rentals
- Long Island Holiday rentals
- Cottage rentals Winchester
- Cabin rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Flat rentals Winchester
- Pet-friendly rentals Winchester
- Family-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Rentals with a patio Winchester
- House rentals Winchester
- Apartment rentals Virginia
- 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
- 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
- Shenandoah Valley Golf Club
- Creighton Farms
- Notaviva Vineyards
- Bowling Green Country Club
- Twin Lakes Golf Course
- Berkeley Springs State Park
- JayDee's Family Fun Center
- River Creek Club
- Reston National Golf Course
- Car and Carriage Caravan Museum
- Dinosaur Land
- Warden Lake
- Hidden Creek Country Club