Condo holiday rentals in Winchester

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Top-rated condo rentals in Winchester

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Guest favourite

Condo in Downtown Frederick

4.89 out of 5 average rating, 111 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 favourite

Condo in Frederick

4.94 out of 5 average rating, 134 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 in Frederick, including Carroll Creek, Baker Park, shopping & breweries. Friendly hosts on-site. Up to 2 house-trained dogs allowed. The only hot tub in downtown, and is for adults only. Guests must climb tall stairs outside and inside. (Grill closed for season.)

Top Guest favourite

Condo in Mercersburg

4.91 out of 5 average rating, 45 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 favourite

Condo in Sterling

4.92 out of 5 average rating, 124 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 favourite

Condo in Downtown Frederick

4.93 out of 5 average rating, 268 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 favourite

Condo in Centreville

4.91 out of 5 average rating, 101 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.

Superhost

Condo in Basye

4.79 out of 5 average rating, 129 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 favourite

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.

Superhost

Condo in Mount Jackson

4.81 out of 5 average rating, 96 reviews

The Room with the Views!

Enjoy a stylish experience at this centrally-located condo at Bryce Resort. This full service four season resort is nestled in the mountains of the Shenandoah Valley. This newly renovated space is great for a ski retreat, mountain biking stay, a golf weekend, or a romantic getaway. The space offers a fully stocked kitchen, washer/dryer, linens, and a fully operational wood burning fireplace (available November- March).

Top Guest favourite

Condo in Bridgewater

4.98 out of 5 average rating, 108 reviews

Wi-Fi, 3 bedroom, 3 bath, near BWC, JMU, 1-81

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.

Guest favourite

Condo in Leesburg

4.93 out of 5 average rating, 190 reviews

Stunning Remodeled 1 BR Condo Steps to Everything.

Large private hideaway, tucked one block from the bustle of King Street. This renovated 2nd floor condo with vaulted ceilings is accessed by a separate secure entrance. Full kitchen includes a 2 top table, toaster, pots & pans, dinnerware, basic cooks tools & coffee maker. Queen size bed with luxury linens & private balcony. 1 full bath. W/D in unit. High Speed Internet. 1 Reserved off street parking space.