Condo vacation rentals in Winchester

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Top-rated condo rentals in Winchester

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Guest favorite

A bronze plaque is mounted on a brick wall, indicating the building's historic status. The plaque features an architectural design and is accompanied by text detailing its significance to the Fauquier Historical Society.

Condo in Warrenton

4.93 out of 5 average rating, 107 reviews

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.

Guest favorite

A modern half bathroom is designed with hexagonal tiles in contrasting black and white patterns. A rectangular mirror with integrated lighting hangs above a wall-mounted sink. A sleek toilet and a small basket for toiletries complete the space, enhancing functionality and style.

Condo in Sterling

4.92 out of 5 average rating, 129 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

The open living and dining area is designed with a modern aesthetic. A comfortable sofa is paired with a wooden coffee table, and two green bar stools complement the kitchen's granite countertop. Soft light illuminates the space, enhancing the cozy atmosphere.

Condo in Downtown Frederick

4.93 out of 5 average rating, 279 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.

Top guest favorite

A historic brick building features multiple stories with green shutters adorning the windows. The entryway is accentuated by stone steps, and a tree provides greenery nearby. The surrounding area includes parked cars and a street sign indicating one-way traffic.

Condo in Fredericksburg

4.95 out of 5 average rating, 255 reviews

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.

Guest favorite

Condo in Centreville

4.92 out of 5 average rating, 107 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 Occoquan

4.92 out of 5 average rating, 773 reviews

The Bird's Nest in Historic Occoquan (Mins to DC)

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 dining 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).

Superhost

Condo in Annandale

4.82 out of 5 average rating, 129 reviews

Remodeled 1BR/1BA Condo: close to DC with pool!

Spacious and completely remodeled condo at Fairfax Heritage. Newly painted and featuring brand new carpet and vinyl flooring throughout the unit. All-new kitchen including stainless steel appliances, cabinets, quartz countertops, sink, lighting and plumbing fixtures. Remodeled bath. Generously-sized bedroom with double closet. Large private balcony overlooking treed courtyard. Common laundry on lower level, private storage unit. Grilling available in picnic area.

Guest favorite

The indoor pool area is spacious, featuring a turquoise water surface under a high, light green ceiling with exposed beams. Sunlight filters through large windows, illuminating several lounge chairs arranged along the side. A bar counter is visible at one end of the pool.

Condo in Basye

4.79 out of 5 average rating, 131 reviews

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.

Guest favorite

An outdoor area shows a snow-covered landscape with a ski slope visible in the background. A building stands prominently in the foreground, flanked by benches. Overcast skies provide a muted backdrop to the scene, enhancing the winter atmosphere.

Condo in Mount Jackson

4.93 out of 5 average rating, 138 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

An open-concept kitchen area reveals a wooden countertop with four seating stools. The kitchen features dark cabinetry and modern appliances. Natural wood paneling accents the ceiling, and a doorway leads to a cozy sleeping area, enhancing the spaciousness of the layout.

Condo in Mount Jackson

4.8 out of 5 average rating, 106 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).

Guest favorite

A sunroom corner features two bookshelves with various books and decorative items. A potted plant adds greenery to the space. Large windows allow natural light to fill the room, providing expansive views of the surrounding area. A modern chandelier provides soft illumination.

Condo in McLean

4.97 out of 5 average rating, 141 reviews

Luxury 1bd in Heart of Tysons

Located in the heart of Tysons next to shopping, restaurants, and 20 minutes from DC. Luxury 1bed/1bath with an incredible high rise view. Work in the sunroom with expansive views of DC or walk downstairs for a coffee. Everything you need for a relaxing vacation or productive work trip. Includes your own dedicated parking spot underground. Enjoy the multi amenity building by using the gym or the rooftop with a pool.

Top guest favorite

A coffee mug with a black and white design featuring the words 'Coffee First' is positioned in the foreground. In the background, two ceramic canisters with textured patterns and wooden lids are visible against a dark countertop and tiled backsplash.

Condo in Bridgewater

4.98 out of 5 average rating, 114 reviews

3 bedroom, 3 bath, near BWC, JMU, 1-81 *WIFI*

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.