Condo vacation rentals in Winchester

Historic Two Bedroom in Old Town Warrenton

Enjoy a stay in our historic, spacious, two-bedroom apartment in Old Town Warrenton. The lower-level unit was lovingly restored with stone walls and a luxurious, charming feel. Centrally located - just a two-minute walk to all restaurants, shopping, and nightlife. It’s a great location to spend time with family and friends. Ample free parking, kitchenette, your own washer and dryer, and more. Everything you need for a perfect stay to feel right at home. Only a modest $38 cleaning fee per stay.

The Grand Delphey: Downtown Artist Retreat

Enjoy this stylish condo located in the heart of downtown's Historic District. The condo resides within a beautiful mansion known as the The Grand Delphey with shared rooms on the first level perfect for photo sessions or gathering. The unit has the ability to rent with 3 other units to SLEEP UP TO 16 PEOPLE! Please let us know if you would like to book the entire mansion for wedding parties or other events. Just steps away from wedding venues, Baker Park, the creek, downtown nightlife & shops!

2 Queen & 1 Twin Bed / Mountain & Museum Fun

Perched well above the city and in between Gambrill State Park and Cunningham Falls State Park, enjoy your stay in this extra large living space. Fifteen minutes from the city limits of Frederick, come and enjoy the peaceful surroundings with all the amenities of modern life. Bring your bikes and hiking boots to experience the myriad of trails and wildlife throughout the region. Close to the quaint City of Frederick. Dozens of wineries, craft breweries, and antique stores located nearby.

The Daisy in Historic Occoquan (Mins to DC)

Modern & spacious condo in the heart of walkable historic Town of Occoquan. Full kitchen, bath, a comfortable queen bed, work station & free parking. The Town of Occoquan offers unique experiences (kayaking, fishing, birdwatching and shopping) all within walking distance. Excellent dinning choices from award winning restaurants to casual eateries. Mins to I-95, 123, VRE. D.C. (35min); Fort Belvoir (20min); The Pentagon (25min); Quantico (25min); Potomac Mills (10min). Tysons (25min).

The Cozy Villa

Home away from home, conveniently located seconds away from Interstate 81 and central to all restaurants and shops! Perfect for a group of traveling friends or a family looking for a peaceful stay. This warm and cozy villa boasts tastefully modern features with 2bdr, 1bth, fully equipped kitchen, living room, dining room, washer/dryer in unit, front and back patio with patio furniture. The home has a driveway so parking is hassle-free! Very quiet and safe neighborhood. Pet friendly.

Peaceful 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, high speed 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, Starbucks, and Restaurants. Less than 2 miles from Spa World. And 10 min drive to King Spa.

Casa 1776 - Spacious Apartment | Heart of Downtown

Rest in the heart of downtown Fredericksburg! You’ll stay in the lower level apartment of this historic home. Constructed during the Revolution, and used as a hospital during the Civil War, this home is directly across from the visitor center, within steps of landmarks, awesome restaurants, taprooms, and shops. It’s the perfect spot for a weekend away or historic excursion. The newly constructed River Front Park sits at the rear of the property and is awesome for the little ones.

Multi-Level Mountain Stay w/ Pool

Relax and recharge in this 2-bedroom multi-level condo at Chalet High, just 2 miles from Bryce Resort in Virginia’s scenic Shenandoah Valley. Featuring a full kitchen, fireplace, and private balcony, it’s ideal for families or couples seeking a cozy mountain escape. Enjoy access to an indoor pool, sauna, hot tub, and fitness center. Whether you're hiking, skiing, or simply unwinding, this peaceful retreat offers year-round comfort and convenience.

3 BR, 3 bath, near BWC, JMU, 1-81 *WIFI* Buccee’s

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.