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Condo vacation rentals in Winchester

Find and book unique condos on Airbnb

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Popular amenities for Winchester condo rentals

Weekly condo rentals

Guest favorite
The image displays a private room featuring two single beds, each with light bedding. A green blanket is draped across one bed. Two small nightstands are positioned next to the beds, contributing to a tidy and functional layout.
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.
A dining area features a rectangular white table surrounded by four chairs. An abstract painting hangs on the light-colored wall. The adjacent kitchen is open, showcasing modern appliances and counter seating with three stools, complemented by contemporary fixtures and soft lighting.
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
A wooden staircase leads up to the apartment entrance, surrounded by a railing and bordered by a grassy area. The steps are framed by a wooden deck and the approach is highlighted by sunlight filtering through nearby trees.
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 favorite
A view of downtown Charles Town at night, illuminated by decorative lights along the buildings. The street is lined with historic architecture, and cars can be seen navigating the roadway. The gentle glow of street lamps adds to the evening ambiance.
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 favorite
A snow-covered landscape at Bryce Resort is framed by bare trees adorned with frost. The glistening white snow blankets the hill, inviting winter activities. The ski lift is visible, indicating access to the slopes, under a clear blue sky with soft clouds.
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
An outdoor dining area is positioned on a wooden deck, featuring a table set with plates and drinks. Surrounding the table are four woven chairs. A soft glow from the sunset illuminates the scene, enhancing the surrounding greenery and distant views.
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 favorite
The living room features a stone fireplace as a focal point, complemented by a cozy chair draped with a blanket. Large windows provide natural light and a view of the outdoors, while a wooden table adds functionality to the space.
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 favorite
A view of Washington Street is captured through the window. The image showcases quaint storefronts along the street, hinting at the vibrant local businesses. The early morning light casts a soft glow on the buildings, and the street appears calm, inviting exploration.
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
The living area features rustic wooden furnishings, including a sofa and coffee table, with a ceiling fan overhead. Natural light filters in through large windows, illuminating the space. A dining table is set for four, while a flat screen TV is positioned nearby.
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 favorite
A covered outdoor patio is presented, featuring a small round table surrounded by two chairs. Decorative string lights are hung above, and a view of snow-capped hills is visible in the background, providing a scenic backdrop for outdoor relaxation.
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 favorite
The exterior entrance features a clean walkway flanked by well-maintained landscaping, including low shrubs and colorful flowers. Two doors are visible, set in a modern light-colored brick facade, with large windows allowing natural light to enter the building.
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 favorite
The illuminated sign of Whitetail Resort is showcased against a winter backdrop, surrounded by snow-covered ground and barren trees. Stone pillars frame the sign, creating a welcoming entrance to the resort.
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
A spacious house is set against a backdrop of vibrant autumn trees, with a well-manicured lawn and curved driveway leading to its entrance. Bushes with red foliage create a contrast with the greenery, while clear blue skies add to the peaceful setting.
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 favorite
A modern living area features a light-colored sectional sofa adorned with a patterned throw. A kitchen with a wood countertop and seating area can be seen in the background, complemented by pendant lighting. Mirrored walls enhance the sense of space, reflecting the inviting atmosphere.
Condo in Mount Jackson
4.87 out of 5 average rating, 97 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

DanRating, 5 stars2 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 favorite
A modern kitchen is depicted, featuring dark cabinetry and stainless steel appliances. An island with seating for two is complemented by a light countertop. Decorative elements include a potted plant and functional items like a trash can, contributing to the efficient design.
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 favorite
A small outdoor patio features a round wooden table set for two, complete with two glasses of white wine and a charcuterie board. The surrounding greenery and distant mountains provide a scenic backdrop, inviting relaxation among nature.
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

An indoor water park is illuminated by sunlight streaming through a large, transparent roof. Water features including slides, a lazy river, and play areas are visible, surrounded by rocks and greenery. Colorful structures add to the lively atmosphere, inviting fun and relaxation.
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.
A bright studio apartment features two beds dressed in plaid bedding. A large flat-screen TV is mounted on the wall, opposite a red vintage refrigerator. Soft lighting lines the ceiling, complementing a warm, comfortable atmosphere.
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!
A spacious bedroom is highlighted by a king bed adorned with a patterned bedspread. Nightstands are positioned on either side, each featuring a lamp. A doorway leads to an adjoining bathroom, while soft green walls contribute to a relaxing ambiance.
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!
A spacious bedroom features a king size bed dressed in patterned linens with warm colors. A pair of bedside lamps provide soft lighting. A comfortable armchair sits beside the bed, and a nightstand holds an alarm clock. The walls are decorated in calming hues.
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
A ski lift is seen against a clear blue sky, with several empty chairs suspended from cables. The background features trees with some remaining foliage, and a building resembling a ski lodge is slightly visible off to the side.
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.
An expansive outdoor pool is surrounded by sun loungers and shaded areas. Adjacent play equipment is visible, adding a recreational element to the area. It is set against a backdrop of rolling hills and a clear sky, providing a relaxing space for guests.
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.
A large swimming pool is surrounded by concrete and bordered by lush trees, providing shade. Several lounge chairs and tables are arranged nearby, creating a recreational area. The sky above features scattered clouds, adding to the outdoor ambiance.
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!
A spacious living area features a comfortable sofa and armchair complemented by a wooden coffee table. Large windows allow natural light to illuminate the room, while warm yellow walls create a cheerful ambiance. A kitchenette is visible in the background, equipped with modern appliances.
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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