Condo vacation rentals in Winchester

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Top-rated condo rentals in Winchester

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Guest favorite

A scenic view of a canal lined with lush greenery and benches. Water lilies float on the surface, while lanterns illuminate the walkway. The tranquil path is flanked by trees and buildings, creating a welcoming atmosphere for leisurely strolls.

Condo in Downtown Frederick

4.89 out of 5 average rating, 112 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

An outdoor dining area is visible on a private brick patio, featuring a table surrounded by chairs. A large umbrella offers shade. Lush greenery and trees are seen beyond the patio, with a charming brick building in the background.

Condo in Warrenton

4.93 out of 5 average rating, 101 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.

Superhost

Condo in Fredericksburg

4.74 out of 5 average rating, 103 reviews

Heart of Downtown Fredericksburg 2 Bedroom Condo

Welcome to a true Downtown Fredericksburg Condo. We are located directly across the street from VRE, Amtrak. Common area tile lobby with high top table and full size washer/dryer. This is a completely private 2 bedroom Condo, vaulted ceilings, new carpet and in a great location. Private off-street parking. Walk to restaurants or shops in historic Fredericksburg within eyesight of your balcony. Skylights, master bedroom bath, fireplace, dining table, desk, Internet , smart TV, cable and Netflix.

Guest favorite

A secluded backyard space features a wooden dining table adorned with decorative items. Colorful umbrellas provide shade over the patio area. String lights create a soft glow, complementing a small fire pit surrounded by chairs, enhancing the inviting atmosphere of the outdoor setting.

Condo in Frederick

4.94 out of 5 average rating, 138 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.)

Guest favorite

A serene river stretches through a lush landscape, bordered by large rocks and trees. The calm water reflects the greenery and rocky shoreline, creating a tranquil scene. The clear blue sky above enhances the peaceful atmosphere.

Condo in Occoquan

4.92 out of 5 average rating, 472 reviews

The Daisy in Historic Occoquan (Mins to DC)

Modern & spacious new 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).

Guest favorite

The exterior of the loft is showcased, featuring a modern two-story structure with a light-colored facade and large windows. The property is surrounded by greenery, and a spacious driveway leads to the entrance, providing ample parking space.

Condo in Sterling

4.92 out of 5 average rating, 125 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

A modern bathroom features a spacious walk-in shower enclosed by transparent glass. White subway tiles adorn the walls, complemented by a sleek marble countertop. A minimalist showerhead and a black faucet provide a contemporary touch, enhancing the clean and functional design of the space.

Condo in Downtown Frederick

4.93 out of 5 average rating, 270 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, 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

A green lawn extends alongside a flowing stream, with a metal grill and a bench positioned for outdoor gatherings. Leafless trees create a natural backdrop, while the multi-level condo units in the distance are visible under a clear sky.

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.

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.

Superhost

A modern living area features a leather sofa paired with a sleek armchair, positioned around a low coffee table. Large windows allow natural light to illuminate the space, showcasing views of the surrounding greenery. A door leads to a private outdoor balcony.

Condo in Mount Jackson

4.8 out of 5 average rating, 99 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 favorite

The kitchen features white cabinetry and granite countertops, with a double basin sink positioned beneath a lighted backsplash. Essential appliances, including a dishwasher and a coffee maker, are neatly arranged on the countertop, providing a functional workspace for meal preparation.

Condo in Bridgewater

4.98 out of 5 average rating, 110 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.