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Condo vacation rentals in Winchester

Find and book unique condos on Airbnb

Top-rated condo rentals in Winchester

Guests agree: these condos are highly rated for location, cleanliness, and more.

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Top guest favorite

A cozy seating area features a patterned sofa and a coffee table, positioned in front of a queen-size bed with red and blue accents. Exposed stone walls create a rustic charm, while soft lighting enhances the inviting ambiance.

Condo in Warrenton

4.94 out of 5 average rating, 118 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.

Top guest favorite

A cozy living space features dark blue walls and large windows allowing natural light. A gray sofa is positioned beside a dining table with modern bar stools. Decorative items and framed pictures enhance the ambiance, while rich wood flooring adds warmth to the room.

Condo in Downtown Frederick

4.97 out of 5 average rating, 114 reviews

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!

A spacious living area features a pool table centered on a patterned rug. Comfortable seating options surround the space, with light-colored walls complementing the decorative elements. A tall plant adds a touch of greenery, while various artwork adorns the walls, contributing to a welcoming environment.

Condo in Frederick

4.96 out of 5 average rating, 117 reviews

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.

Top guest favorite

A spacious living area features a light-colored sectional sofa paired with vibrant accent pillows. A wooden coffee table sits in front, complementing the warm wooden flooring. The adjacent kitchen showcases turquoise cabinetry and modern bar stools, with large windows allowing natural light to fill the space.

Condo in Sterling

4.93 out of 5 average rating, 148 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.

Top guest favorite

A living room features navy blue sofas adorned with throw pillows, facing a wooden coffee table atop a patterned rug. A circular mirror and a decorative plant are visible on the wall, while a dining area with a white table and chairs is illuminated by natural light from large windows.

Condo in Martinsburg

4.98 out of 5 average rating, 113 reviews

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.

A light-filled living area features a comfortable sectional sofa adorned with neutral tones and decorative cushions. The circular area rug in soft blue anchors the space, complemented by abstract art pieces on the wall and a modern mirror reflecting natural light.

Condo in Centreville

4.92 out of 5 average rating, 120 reviews

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.

A serene bedroom features a king bed with a tufted headboard, complemented by decorative pillows. Warm lighting is provided by bedside lamps on each side. A light-colored sofa with a subtle design sits at the foot of the bed, and natural light enters through the window with white shutters.

Condo in Downtown Frederick

4.93 out of 5 average rating, 289 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 cozy loft bedroom features a spacious bed with light bedding. A bedside table with a lamp is present, and a decorative pillow with 'welcome to our cabin' is displayed. Natural light filters through a triangular window, highlighting the wooden beams of the ceiling.

4.99 out of 5 average rating, 135 reviews

Dog Friendly 3BR/2BA with Loft and Mountain Views

Escape to our renovated condo with stunning mountain views near Bryce Resort! This 3BR/2BA condo is perfect for families seeking adventure or relaxation in the Shenandoah Valley. Pet-friendly (dogs only due to owner's allergies), stocked with kitchen supplies, and walkable to the grocery store. Our condo sleeps 6 (max per county code). No parties and no smoking. Loft acts as an approved, legal third bedroom per Shenandoah County. Book now for an unforgettable family getaway!!

Top guest favorite

Condo in Frederick

4.95 out of 5 average rating, 153 reviews

Quiet Stay + Huge Apt + Hot Tub + Dogs, Walkable

Hot tub. Peace and quiet — in downtown. Whether you're visiting for a romantic weekend, catching up with an old friend, or traveling solo with your dog, this oversized two-floor downtown Frederick flat gives you the space (and quiet) to unwind. A private hot tub, sun-drenched rooms, and vintage charm, this thoughtfully designed space is perfect for relaxing after a day of exploring Frederick. Walk to breweries, coffee shops, boutiques, and local restaurants. Dog-friendly

A modern living area features a light-colored sectional sofa adorned with a patterned throw. A kitchen with a wood countertop and seating area can be seen in the background, complemented by pendant lighting. Mirrored walls enhance the sense of space, reflecting the inviting atmosphere.

Condo in Mount Jackson

4.86 out of 5 average rating, 102 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

This recently renovated, modern condo offers the latest amenities, including WIFI and Smart TVs. The true charm lies in its outdoor options. Sip a hot drink on the balcony, watch the sunset, or cozy up by the fireplace. In the season, enjoy the Community Pool, explore slopes, lifts, dining, and shops nearby. Golfing, skiing, biking, ziplining, swimming, and canoeing at Lake Laura are a short walk away. Embrace modern comfort and thrilling outdoor adventures!

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.

4.79 out of 5 average rating, 135 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.

A cozy living area features two gray sofas positioned around a wooden coffee table. Decorative throw pillows on the sofas offer a hint of warmth. The background reveals an open kitchen with modern fixtures and a light-colored aesthetic, enhancing the space's inviting feel.

Condo in Mount Jackson

4.93 out of 5 average rating, 141 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.

Vacation rentals for every style

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Quaint homes, peaceful surroundings

Apartments

Convenient locations with everyday essentials

Popular amenities for Winchester condo rentals

Free parking on premises

Air conditioning

Weekly condo rentals

A dining table is set for six with floral-patterned plates, cups, and a teapot, creating an inviting space for meals. The background reveals an open living area with bright lighting and access to the retreat's comfortable seating.

Condo in Penn Laird

5 out of 5 average rating, 6 reviews

Crawberry Basement Retreat

An expansive covered deck features a seating area with white chairs and a table, surrounded by panoramic views of the historic town. A grill and a fire pit are visible, while planters with greenery add a natural touch to the inviting outdoor space.

Condo in Cumberland

4.73 out of 5 average rating, 11 reviews

Romantic condo with a view in historic Cumberland

A seating area is highlighted by a comfortable sectional sofa facing a stone fireplace, which features a mounted television above it. Natural light enters through the slanted ceiling, enhancing the cozy ambiance of the space.

5 out of 5 average rating, 7 reviews

“Osprey’s Nest” cozy condo escape Bryce Resort

A spacious living room features comfortable seating arrangements, including a leather sofa and a fabric couch. A wood-burning fireplace is surrounded by a stone facade, and a flat-screen TV is mounted above it. Large windows provide natural light, enhancing the relaxing atmosphere.

4.9 out of 5 average rating, 29 reviews

Lovely 2 Bedroom Condo

A scenic view captures the sun rising above rolling hills, with soft rays illuminating the landscape. Trees with green foliage frame the foreground, creating a sense of tranquility and connection to nature.

Condo in Massanutten

4.92 out of 5 average rating, 12 reviews

Luxury 2BR 2BA w Hot Tub bath at Massanutten

A bright living area features a spacious bed with crisp white bedding and a cozy armchair nearby. A small kitchenette is visible in the background, complemented by a dining table paired with black chairs. Green plants add a touch of nature to the decor.

Condo in Leesburg

4.92 out of 5 average rating, 39 reviews

Entire Condo - Walkable Downtown Leesburg

An inviting living area features a combination of brown and beige seating, including a sectional and a pair of armchairs. A coffee table sits centrally on a patterned rug, while framed photographs are displayed on the wall. Natural light enters through the windows covered by light drapes.

Condo in Mercersburg

4.5 out of 5 average rating, 4 reviews

Slope-side Studio Condo

A two-story building featuring a combination of wood and stone exteriors, with multiple balconies visible. The landscaped area includes greenery and small trees, set against a clear blue sky. Parking spaces are situated in the foreground.

Condo in Massanutten

4.67 out of 5 average rating, 3 reviews

Spring Break Get-Away for the Family

Pet-friendly condo rentals

The exterior of a two-story farmhouse is captured, featuring a green metal roof and white brick walls. Green shutters frame large windows, and an American flag is displayed prominently. A covered porch with a bench provides a welcoming entrance, set amidst well-maintained greenery.

4.6 out of 5 average rating, 5 reviews

Farm house suite!

Top guest favorite

The illuminated sign of Whitetail Resort is showcased against a winter backdrop, surrounded by snow-covered ground and barren trees. Stone pillars frame the sign, creating a welcoming entrance to the resort.

Condo in Mercersburg

4.92 out of 5 average rating, 49 reviews

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

A spacious house is set against a backdrop of vibrant autumn trees, with a well-manicured lawn and curved driveway leading to its entrance. Bushes with red foliage create a contrast with the greenery, while clear blue skies add to the peaceful setting.

Condo in Culpeper

4.92 out of 5 average rating, 13 reviews

Private 2/2 full baths very bright basement home

The living area features rustic wooden furniture, including a sleeper sofa and a dining table. A stone fireplace creates a central focal point, while a flat screen TV is positioned within view. Natural light filters through large windows, illuminating the space.

4.8 out of 5 average rating, 5 reviews

Ski/MTB/Golf Condo (#125) - Slope & Resort views!

Condo in Downtown Frederick

New place to stay

Cozy Fall Vibes - 9 Min Walk to Carroll Creek!

A small outdoor patio features a round wooden table set for two, complete with two glasses of white wine and a charcuterie board. The surrounding greenery and distant mountains provide a scenic backdrop, inviting relaxation among nature.

4.89 out of 5 average rating, 47 reviews

Mountain View’s, pet friendly, near Bryce Resort

A snow-covered landscape is shown, with a view of the building housing the condo on the left. Ski lift towers rise in the distance, surrounded by trees. The clear blue sky offers a bright backdrop, emphasizing the winter setting.

Condo in Mercersburg

4.97 out of 5 average rating, 35 reviews

Cozy, renovated Ski & Hiking Getaway - Whitetail

A private deck is featured, furnished with comfortable seating and a striped throw pillow. A wooden coffee table sits on a patterned outdoor rug, surrounded by greenery. The natural wood railing enhances the connection to the surrounding trees and serene landscape.

4.93 out of 5 average rating, 76 reviews

Woodland Haven in Bryce Resort

Condo rentals with a pool

Top guest favorite

An outdoor pool area is presented, featuring a clear, inviting swimming pool surrounded by lounge chairs. Two cabanas are visible, providing shaded seating areas. The poolside is bordered by a smooth concrete surface, complemented by greenery in the background.

Condo in Mercersburg

5 out of 5 average rating, 23 reviews

SlopeSide

A spacious lawn is surrounded by lush trees, creating a serene outdoor area. In the foreground, a fire circle is visible, accompanied by a set of outdoor chairs. The recently renovated three-story condo is seen in the background, harmoniously integrated into the natural setting.

4.82 out of 5 average rating, 17 reviews

Redwood 2 Condo Graves Mountain Farm in Blue Ridge

A series of modern, two-story condo units is surrounded by lush greenery and rolling hills. Wooden walkways lead to the entrances, providing easy access from the parking area. Large windows allow natural light to fill the interiors, complementing the serene outdoor setting.

Condo in Massanutten

Eagle Trace Condo at Massanutten 1br/1ba hottub

A series of ski gondolas are seen ascending a mountain, suspended from overhead cables. Snow-covered slopes can be observed below, with a bright blue sky providing a clear backdrop. The gondolas feature large windows, allowing views of the winter landscape.

Condo in McGaheysville

4.84 out of 5 average rating, 144 reviews

Massanutten Woodstone 2-BR, 2 Bath

A spacious bedroom is highlighted by a king bed adorned with a patterned bedspread. Nightstands are positioned on either side, each featuring a lamp. A doorway leads to an adjoining bathroom, while soft green walls contribute to a relaxing ambiance.

Condo in Massanutten

4.5 out of 5 average rating, 107 reviews

Massanutten Woodstone 1 Bedroom Standard Condo

A comfortable living area features a stone fireplace adorned with greenery. A brown sectional sofa is positioned around a small wooden coffee table. A television is mounted on the wall, and ski equipment is visible nearby, enhancing the cozy ambiance.

Condo in Mount Jackson

4.89 out of 5 average rating, 75 reviews

Cozy condo at Bryce Resort

A ski lift is seen against a clear blue sky, with several empty chairs suspended from cables. The background features trees with some remaining foliage, and a building resembling a ski lodge is slightly visible off to the side.

Condo in Mount Jackson

4.63 out of 5 average rating, 16 reviews

Aspen East 313/314 -- SKI-IN/SKI-OUT!

The image captures a scenic view of ski lifts and the surrounding landscape, showcasing a grassy area leading to the slopes. Nearby buildings and trees are visible under a clear blue sky, creating a connection with the outdoor environment.

Condo in Mount Jackson

4.95 out of 5 average rating, 128 reviews

Aspen’s Slope Side Condo at Bryce Resort

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