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Condo holiday rentals in Winchester

Find and book unique condos on Airbnb

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Popular amenities for Winchester condo rentals

Weekly condo rentals

Guest favourite
Condo in Annandale
4.81 out of 5 average rating, 16 reviews

Clean Condo in Annandale.

TaliaRating, 5 stars1 week ago
Stay met our needs! Kitchen was very nice to cook in and was very clean.
Condo in Downtown Frederick
4.79 out of 5 average rating, 203 reviews

Modern Condo In Downtown Frederick

JosephRating, 5 stars1 month ago
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
Condo in Harpers Ferry
4.63 out of 5 average rating, 38 reviews

Memory Lane

DominicRating, 5 stars10 months ago
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!
Guest favourite
Condo in Charles Town
5 out of 5 average rating, 19 reviews

Upscale Walkup Apartment

MichaelRating, 5 stars1 month ago
Nice, clean place. Good location for that area.
Guest favourite
Condo in Mount Jackson
4.89 out of 5 average rating, 74 reviews

Cozy condo at Bryce Resort

PhillRating, 5 stars4 months ago
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.
Superhost
Condo in Downtown Frederick
4.78 out of 5 average rating, 9 reviews

Lark's Nest on Market

KathleenRating, 5 stars14 months ago
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.
Guest favourite
Condo in Mount Jackson
4.94 out of 5 average rating, 90 reviews

Condo at Bryce Resort

LynnRating, 5 stars4 weeks ago
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
Guest favourite
Condo in Charles Town
4.73 out of 5 average rating, 120 reviews

2 Bed Condo at Abolitionist Ale Works #300

TimothyRating, 5 stars2 months ago
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

Superhost
Condo in Basye
4.67 out of 5 average rating, 6 reviews

Ski/MTB/Golf Condo (#122) - Mountain views!

DavidRating, 5 stars7 months ago
Great location for riding. Our stay was great
Guest favourite
Condo in Mercersburg
4.82 out of 5 average rating, 65 reviews

Ski🎿 & hike from front steps—Mountainside getaway

MarkRating, 5 stars3 months ago
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!
Guest favourite
Condo in Gaithersburg
5 out of 5 average rating, 11 reviews

1 Bed/1 Bath/1Pkg Space|Dogs-OK

AlashleRating, 5 stars1 month ago
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.
Top Guest favourite
Condo in Mercersburg
4.91 out of 5 average rating, 46 reviews

Whitetail Resort Ski-in/Ski-out slope side condo.

KayleeRating, 5 stars3 months ago
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.
Superhost
Condo in Culpeper
4.92 out of 5 average rating, 13 reviews

Private 2/2 full baths very bright basement home

KariRating, 5 stars7 months ago
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.
Guest favourite
Condo in Mount Jackson
4.87 out of 5 average rating, 97 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

DanRating, 5 stars3 weeks ago
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!
Guest favourite
Condo in Manassas
4.85 out of 5 average rating, 66 reviews

Perfect Location Old town / walk to the metro

DorisRating, 5 stars4 days ago
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!
Guest favourite
Condo in Basye
4.85 out of 5 average rating, 33 reviews

Mountain View’s, pet friendly, walk to Lake Laura

StephanieRating, 5 stars2 days ago
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

Condo in Massanutten
4.67 out of 5 average rating, 3 reviews

Summit Hillside at Massanutten

KristaRating, 5 stars19 months ago
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.
Condo in Mercersburg
4.56 out of 5 average rating, 34 reviews

The Music Room at Ski Whitetail!

KendraRating, 5 stars4 months ago
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!
Condo in Massanutten
4.51 out of 5 average rating, 94 reviews

Massanutten Woodstone 1 Bedroom Standard Condo

AshleyRating, 5 stars3 weeks ago
Great little weekend getaway! The one bedroom Condo with partial kitchen was perfect! Tons of activities to do around the resort! We will return!
Condo in Massanutten
4.92 out of 5 average rating, 12 reviews

Luxury 2BR 2BA w Hot Tub bath at Massanutten

AmitRating, 5 stars29 months ago
Great place and responsive host.
Superhost
Condo in Mount Jackson
4.63 out of 5 average rating, 16 reviews

Aspen East 313/314 -- SKI-IN/SKI-OUT!

DanielRating, 5 stars4 months ago
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.
Condo in Massanutten

The Summit at Massanutten 2br suite, Saturday chec

StevenRating, 5 stars1 month ago
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.
Condo in Fairfax
4.61 out of 5 average rating, 18 reviews

Lovely 2-bedroom condo with pool and gym

TanishaRating, 5 stars1 month ago
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!
Condo in Massanutten
4.67 out of 5 average rating, 3 reviews

Spring Break Get-Away for the Family

MarniRating, 5 stars70 months ago
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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