
Condo vacation rentals in Winchester
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Top-rated condo rentals in Winchester
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Popular amenities for Winchester condo rentals
Weekly condo rentals

Clean Condo in Annandale.
Stay met our needs! Kitchen was very nice to cook in and was very clean.

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.

Cozy condo at Bryce Resort
We were here for a brief weekend getaway to go snowboarding with the family. It was exactly what we were looking for. It was ski in/out with only a 5-6 minute walk to the bunny slope and lifts. The bed was very comfortable.

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.

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.
Pet-friendly condo 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.

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.

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!

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.
Condo rentals with a pool

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!

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.

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.

The Summit at Massanutten 2br suite, Saturday chec
The place was absolutely gorgeous and the apartment was very nice. We had an issue at check-in because the instructions stated to go to the South Lobby for a Saturday check-in, but it was closed and we had to go to the North Lobby. Please update the instructions.

Lovely 2-bedroom condo with pool and gym
Nadia was fantastic to work with as we were dealing with a stressful situation that required a quick exit from our home. She made every effort to get us in early even with a same-day guest departure. The apartment is absolutely perfectly stocked! So many thoughtful items made our stay very comfortable and easy. I wish we’re could have stayed longer to enjoy it all! The pond and geese/ducks outside the master bedroom were lovely (and made good sleeping white noise). Highly recommend if you’re in need of a convenient place in the area!

Spring Break Get-Away for the Family
We love Massanutten Resort and we got a better deal using Horace and Air bnb than the sale special offered at the resort!
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- Luray Caverns
- Cunningham Falls State Park
- Stone Tower Winery
- Cacapon Resort State Park
- Robert Trent Jones Golf Club
- Bryce Resort
- Whitetail Resort
- Gambrill State Park
- South Mountain State Park
- Whiskey Creek Golf Club
- Shenandoah Valley Golf Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Creighton Farms
- Twin Lakes Golf Course
- Berkeley Springs State Park
- Bowling Green Country Club
- Reston National Golf Course
- JayDee's Family Fun Center
- River Creek Club
- Car and Carriage Caravan Museum
- Warden Lake
- Herndon Centennial Golf Course
- Dinosaur Land