Condo vacation rentals in Winchester

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Top-rated condo rentals in Winchester

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Guest favorite

Condo in Downtown Frederick

4.89 out of 5 average rating, 109 reviews

Newly Renovated HUGE condo in heart of downtown!

Our brand new totally upgraded and renovated condo is in the heart of downtown Frederick’s main square. The whole group will enjoy easy access to everything from this centrally located place. This unique historic building has a private parking spot, and access to prime shopping and dining just steps from your door. Although this is an apartment, don’t let it fool you! This 2,000+ sq foot beauty will give you enough space to spread out and relax! This building has the ability to sleep 16!Ask host

Guest favorite

Condo in Herndon

4.94 out of 5 average rating, 141 reviews

Lovely 3 bedroom / 2.5 bath - Whole Condo

You and your family or friends are welcome to this lovely condo. Located conveniently near IAD and a short drive from DCA aiports. Also, located minutes from the metro station into Washington, DC. Family-friendly neighborhood with parking on property with additional in nearby lot. Full kitchen, living room, 1 king, 1 queen bed, and a queen pull out sofa bed. Highest speed Wi-Fi with office available for entertainment and work. One of Virginia's best areas for dining out - A foodie's dream :)

Guest favorite

Condo in Mercersburg

4.9 out of 5 average rating, 41 reviews

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

Enjoy the luxury of putting on your skis at the front door! Large one-bedroom condo with ski lodge ambience: first floor, street level entrance, gas fireplace, wi-fi plus TV, large, fully applianced kitchen, washer/dryer, and one dedicated parking space in front of condo. Check Whitetail Resort website for night-skiing and snow park days. Comfortably sleeps 4; however, large leather sofa accommodates for a 5th. Summertime? Enjoy golf, hiking, fishing, biking, tennis, hot tub, swimming.

Guest favorite

Condo in Frederick

4.94 out of 5 average rating, 127 reviews

Quiet Apartment, Hot Tub, Downtown Frederick, Dogs

Welcome to our beautifully designed 2BR/2BA duplex in the heart of downtown Frederick. In a quiet neighborhood, this charming and spacious 1915 apartment has a fully stocked kitchen, smart TVs, AC, & fire pit. Walk to everything Frederick has to offer including Carroll Creek, Baker Park, shopping & breweries. Friendly hosts on-site. Up to 2 house-trained dogs allowed. Perfect for business & weekend travelers. Guests must climb tall stairs outside and inside. (Grill closed for season.)

Guest favorite

Condo in Sterling

4.92 out of 5 average rating, 119 reviews

The Loft at Lakeside

Welcome to the The loft at Lakeside! The loft is a completely separate space that comes with its own entrance and parking space. The loft consists of a spacious bedroom with a walk-in closet. There is a full bathroom in the bedroom and a half bath near the kitchen. The main space consists of spacious Kitchen that sits right next to the cozy family room, with a large couch. It also has a full laundry room for anyone looking to take home clean clothes after an amazing stay at The Loft.

Guest favorite

Condo in Downtown Frederick

4.93 out of 5 average rating, 263 reviews

Your Hideaway awaits/1-bedroom downtown pad.

There is no place like home when you visit our cozy 1 bed/1 bath abode! This 2nd floor unit is nestled in the rear of a historic home that has been converted into condo living. This space checks all the boxes for a weekend getaway or long-term stay. Enjoy an open living/dinning area, a new memory foam king bed, & a fully furnished bathroom! We offer a keyless entry & 1 parking spot - a rarity for downtown living. Residents live above & below. NO pets, loud music, or parties.

Guest favorite

Condo in Centreville

4.91 out of 5 average rating, 100 reviews

Peaceful resort- like patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front. This home provides a perfect setting for both luxurious and comfortable living. Bright southern exposure, No steps from parking, 2 smart TV, Highspeed internet, queen size bed, the patio opens to private green nature. Plenty of guest parking as well. Long paved walking trail passing by, Walk to Giant, Starbuck, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

Guest favorite

Condo in Mount Jackson

4.94 out of 5 average rating, 122 reviews

Aspen’s Slope Side Condo at Bryce Resort

The only true Ski in/Ski out, first-floor, slope side condo has all of the amenities and comforts of home. Clean, easily accessible and centrally located for a couple or small family. Close to everything, yet private enough to enjoy a relaxing trip. An ideal home base to explore Bryce Resort! Whether you’re in the area to hike, view fall foliage, mountain bike, golf, speed down the slopes or just spend a relaxing weekend in, our condo can accommodate just about everything.

Superhost

Condo in Basye

4.79 out of 5 average rating, 126 reviews

2BR @ Chalet High - Basye, VA

Enjoy a relaxing stay in this cozy two-bedroom, multi-level condo at Chalet High Resort in Basye, VA. Perfect for families, the home features a spacious living area with a fireplace, fully equipped kitchen, and private balcony with mountain views. Located minutes from Bryce Resort, enjoy easy access to skiing, golf, hiking, and more. Resort amenities include an indoor pool, fitness center, and tennis courts, making it the perfect getaway for both adventure and relaxation.

Superhost

Condo in Basye

4.5 out of 5 average rating, 4 reviews

Mountain Condo (#2-301) | Top-level w/ loft

This comfortable condo is located within the first of two mountainside condo buildings overlooking the Bryce Resort golf course (winter views are best, although leaf cover creates a private, secluded experience). Located on a quiet 2-acre parcel at the end of a mountain road, this unit is only 1.4 miles to Bryce Resort’s main lodge, golf course, ski/bike lifts, and restaurant & bar. The condo is also 1.4 miles away from the Basye Community Store.

Guest favorite

Condo in Mount Jackson

4.93 out of 5 average rating, 137 reviews

Ski and Golf Condo Aspen East Condos Unit 212

Newly renovated condo located at Bryce Resort on ski slopes and golf course. This second floor condo faces the golf course with mountain views. Ski in and ski out. Walk to all of Bryce Resort’s amenities including events at the Shenandoah Center. Fully equipped kitchen with Keurig. 2 queen beds and 1 single bed. Wood burning fireplace. Smart TV’s in living room and bedroom. Washer and dryer. Walk-in shower. Wi-fi. Outdoor pool open seasonally.

Guest favorite

Condo in Bridgewater

4.98 out of 5 average rating, 105 reviews

*Wifi* 3 Bedroom home* Near Bridgewater College

Kitchen * Wi-fi * Free Parking * Air Conditioning. This beautiful townhouse is located in the heart of the Shenandoah Valley in the quaint, small town of Bridgewater, Virginia. It is located very near Bridgewater College and the Bridgewater Retirement Home. It is also within a few minutes of EMU (Eastern Mennonite University), JMU (James Madison University). and Dynamic Aviation and has easy access to I-81.