Condo vacation rentals in Winchester

4.94 out of 5 average rating, 120 reviews

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

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.

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.

4.97 out of 5 average rating, 118 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!

4.96 out of 5 average rating, 119 reviews

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

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.

4.93 out of 5 average rating, 151 reviews

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

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.

4.98 out of 5 average rating, 113 reviews

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

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.

4.92 out of 5 average rating, 120 reviews

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

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.

4.93 out of 5 average rating, 290 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.

4.92 out of 5 average rating, 800 reviews

A bright studio space features a queen bed with cozy linens and decorative pillows. A sofa provides additional seating, while a desk and chair are positioned near a window. Light wood flooring and neutral walls create an open and welcoming atmosphere.

Condo in Occoquan

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

Spacious condo in the heart of walkable historic Town of Occoquan. Second floor loft with full kitchen, bath, a comfortable queen bed, work station, w/d in unit & one free parking spot. 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); Quantico (25min); Potomac Mills (10min). Tysons (25min).

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, 137 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!!

4.95 out of 5 average rating, 154 reviews

Condo in Frederick

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

The living area features a stone fireplace, complemented by a stack of firewood beside it. A large leather sofa and a sleek black armchair surround a round table, while expansive windows provide natural light and views of the outdoors.

4.8 out of 5 average rating, 121 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).

4.98 out of 5 average rating, 130 reviews

A light-filled living area features a spacious sectional sofa paired with two side chairs. A wooden coffee table is centrally positioned on a soft area rug. Large sliding doors lead to an exterior space, while a smart TV is mounted against the wall.

Condo in Bridgewater

3 BR, 3 bath, BWC, EMU, JMU, 1-81 *WIFI* Buccees

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.

Popular amenities for Winchester condo rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Weekly 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.

Condo in Luray

4.6 out of 5 average rating, 5 reviews

Farm house suite!

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 serene bedroom features a spacious bed with a decorative floral bedspread and soft pillows. Two bedside lamps illuminate the room, while natural light enters through the nearby window, complemented by floor-length curtains. A wooden desk and chair provide additional functionality.

Condo in Massanutten

4.71 out of 5 average rating, 45 reviews

Massanutten Woodstone 2 Bedroom Full Kitchen Condo

5 out of 5 average rating, 6 reviews

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

Crawberry Basement Retreat

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 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.

Condo in Syria

4.82 out of 5 average rating, 17 reviews

Redwood 2 Condo Graves Mountain Farm in Blue Ridge

A spacious living area features wooden flooring and a comfortable seating arrangement. A television is positioned against one wall, while a decorative wall hanging adds color above the sleeping area, which includes a well-made king-size bed framed by soft lighting.

Condo in Harpers Ferry

4.63 out of 5 average rating, 46 reviews

Memory Lane

4.92 out of 5 average rating, 13 reviews

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

Private 2/2 full baths very bright basement home

Pet-friendly condo rentals

A spacious living area features comfortable seating with two gray armchairs and a beige sofa. A decorative area rug lies beneath a trio of coffee tables. Natural light filters through the large windows, highlighting the exposed brick wall and modern decor.

4.8 out of 5 average rating, 230 reviews

Luxury Condo In Downtown Frederick

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.

4.92 out of 5 average rating, 50 reviews

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

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.

4.86 out of 5 average rating, 102 reviews

Bike,Hike,Relax in Lux! at Bryce Resort

A comfortable blue sofa is positioned in front of a neutral wall, complemented by decorative artwork. Two brown cushions add subtle contrast. A floor lamp with a woven shade provides soft illumination, while a small table with a plant and a lamp is situated nearby.

Frederick 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.

4.9 out of 5 average rating, 50 reviews

Mountain View’s, near Bryce Resort, pet friendly

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.

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.

4.94 out of 5 average rating, 77 reviews

Woodland Haven in Bryce Resort

4.63 out of 5 average rating, 19 reviews

A large swimming pool is surrounded by concrete and bordered by lush trees, providing shade. Several lounge chairs and tables are arranged nearby, creating a recreational area. The sky above features scattered clouds, adding to the outdoor ambiance.

Condo in Fairfax

Lovely 2-bedroom condo with pool and gym

Condo rentals with a pool

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.

5 out of 5 average rating, 23 reviews

SlopeSide

The living area features rustic wooden furniture, including a sofa and coffee table, arranged around a flat screen TV beneath a ceiling fan. A stone fireplace adds a cozy element, while a small dining table sits near the kitchenette. Light enters through multiple windows.

4.88 out of 5 average rating, 8 reviews

Ski/MTB/Golf Condo (#101) - Walk out to slopes!

A spacious room is highlighted by a king-sized bed with a checkered blanket and a bedside lamp. A small dining table with two chairs is situated near the entrance, while the walls are painted in a calming blue tone, complemented by soft lighting.

4.95 out of 5 average rating, 19 reviews

Rockwell Suite #104 at the Inns of Whitetail

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

4.84 out of 5 average rating, 144 reviews

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

Massanutten Woodstone 2-BR, 2 Bath

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.

4.89 out of 5 average rating, 76 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.

4.65 out of 5 average rating, 17 reviews

Aspen East Double Unit-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.