Holiday rentals in South Riding

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Top-rated holiday rentals in South Riding

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

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Top guest favourite
A modern living area is highlighted by a comfortable sectional sofa adorned with colorful cushions. A round coffee table sits in front, with a decorative item placed on top. Large windows allow natural light to illuminate the space, framed by soft curtains and offering views of greenery outside.
Flat in Sterling
4.99 out of 5 average rating, 109 reviews

The Potomac Perch-Peaceful Cozy Family Apt

Step into a calming and contemporary haven. This thoughtfully designed one-bedroom apartment features a spacious bedroom with full bathroom , a modern full kitchen perfect for preparing your favorite meals, and comfortable living areas. The bright and airy layout, with its clean lines and tasteful decor, creates an inviting atmosphere for relaxation after a day of exploring. Nestled in a quiet and peaceful neighborhood along Broad Run Drive, you'll be just moments from the scenic Potomac River.

Top guest favourite
The recently renovated stone cottage features rustic charm with a modern metal roof. Large windows invite natural light, and the outdoor patio area is equipped with seating and an umbrella for shade, surrounded by greenery and trees.
Guest house in Middleburg
5 out of 5 average rating, 130 reviews

18th Century Middleburg Cottage

This recently renovated 2-story 18th Century stone cottage is the perfect blend of rustic and luxury, featuring stone walls, exposed beams, wood floors, a stone patio and outdoor fireplace, as well as Mountain views. Property includes kitchen, bathroom, and a living space with wood stove and dining table. Upper floor features bedroom and additional reading room. Cottage is just minutes from historic Middleburg in the heart of horse and wine country, perfect for relaxing or recharging getaways.

Top guest favourite
A scenic outdoor area featuring a bright green lawn with two chairs positioned nearby. A dining table with a large umbrella is visible, creating a shaded spot for relaxation. The house displays vibrant greenery and colorful foliage under a clear blue sky.
Barn in Haymarket
4.97 out of 5 average rating, 67 reviews

Charming Cottage on Horse Farm

Our distinctive newly renovated 2 bedroom, 2 story, barn apartment with a fully equipped kitchen and elevated deck offers tranquil views of horse fields, a small pond home to wild geese and ducks, and picturesque scenery of the Bull Run Mountains. The deck off the master bedroom offers tranquil views of the horse farm. Additionally, this rental includes a private yard with a charcoal grill and picnic table to relax and cook dinner. Please note this rental does not allow pets, no exceptions.

Top guest favourite
A modern kitchen is highlighted by clean lines and neutral colors. An island with seating is centered, surrounded by a spacious layout. Appliances include a refrigerator and stove, while artwork adorns the walls, contributing to the inviting environment. Ample natural light illuminates the area.
Tiny home in Reston
5 out of 5 average rating, 164 reviews

Pristine 1BR, king bed, hot tub, close to IAD

Luxurious, private and serene. Central location – 1 mile to the Metro, 8 minutes to IAD and Reston Town Center. Dedicated street parking. Close to multiple shops and restaurants. 2 patios and a side yard. Private use of the spacious hot tub with over-sized towels & luxurious robes. Enormous king-size Sleep Number® bed for exceptional comfort. Chef-worthy kitchen and washer/dryer. Free Netflix, YouTubeTV and Prime; your own thermostat and ultra-fast WiFi. No shared spaces. Built new in 2023.

Top guest favourite
A spacious bathroom features a stand-alone tub with elegant legs at the center. Natural light enters through double French doors, leading to views of the lush backyard. A vanity with a mirror and wall-mounted sconces complements the warm-toned wooden floor.
Home in The Plains
5 out of 5 average rating, 37 reviews

The Garden House

The Garden House is the perfect place for two couples, or a group of five, to gather in a secluded setting in the center of the village of The Plains. The newly-renovated 19th century farmhouse shares a front garden with a one-bedroom guest house, The Artist's Cottage (listed separately on Airbnb). Excellent restaurants, a coffee shop, and art galleries are just around the corner. The Plains is a center for equestrian events, biking, and vineyards in the Blue Ridge Mountain foothills.

Top guest favourite
The cottage is a charming two-story building, featuring a dark exterior with large windows. A welcoming porch is accented by steps leading to the entrance, and a stone pathway guides through the lush green yard, surrounded by trees.
Cottage in Leesburg
4.92 out of 5 average rating, 397 reviews

The Cottage at Forest Hills Farm

Beautiful one bedroom, one bath cottage on a picturesque 14 acre farm just outside of downtown Leesburg. Nestled in close to local vineyards, this charming, free-standing cottage is yours and perfect for a weekend getaway or alternative to a hotel. Enjoy the fresh air, beautiful views, and peace and quiet on our little farm. Wander the property and say hello to our donkey, mule, Long Horn cows, goats, chickens, and 3 barn cats (and 3 kiddos!). Just 3 miles to downtown Leesburg.

Guest favourite
Apartment in Centreville
4.9 out of 5 average rating, 136 reviews

Peaceful patio condo

Stylish 1 bedroom condo on ground level with 1 designated parking space directly in front and visitor parking around. 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. Long paved walking trail passing by, Walk to Giant, Starbucks, and Restaurants. Less than 2 miles from Spa World, 10min drive to King Spa.

Top guest favourite
The open living area features comfortable seating arranged around a circular table. Natural light floods the space through multiple windows, highlighting the light colors of the decor. Wood beams add a subtle architectural element, while a patterned rug anchors the seating area.
Home in Leesburg
5 out of 5 average rating, 201 reviews

Downtown Leesburg Cottage. Walk to everything!

Beautiful cottage in Downtown Leesburg! Walkable to all that Downtown has to offer! Across the street from the iconic Mom's Apple Pie and a short walk to restaurants, shopping, breweries and W&OD trail. Just a short drive to many local wineries, wedding venues, hiking and only 20 minutes from the Dulles Airport. Escape for the weekend or week and enjoy this beautiful 2 bedroom/1 bath home. Equipped with the essentials you need for a more than enjoyable stay!

Top guest favourite
The exterior of the cottage is shown, featuring a light-colored wooden structure with a metal roof. Lush greenery surrounds the building, with carefully landscaped flower beds and a stone pathway leading to the entrance. Natural light enhances the inviting atmosphere of the setting.
Farm stay in Purcellville
4.99 out of 5 average rating, 386 reviews

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

Top guest favourite
A modern kitchen and living area are showcased, featuring a large central island with seating for six. Two prominent horse portraits hang above the island, while the sleek design is complemented by gold accents and a mix of light and dark tones throughout the space.
Barn in Middleburg
4.98 out of 5 average rating, 107 reviews

The Studio

🐞1 mile from the center of Middleburg, this gem allows you to enjoy the beauty of a gorgeous Middleburg Farm when you stay in this unique tractor barn turned high end luxury studio apartment! This is for the customer who wants to experience country living but does not want to give up any luxury 🎶 We host travelers and dreamers, not DJs and dance floors—no weddings or events, please. 🚭 Smoking is strictly prohibited anywhere on the property.

Guest favourite
A modern living area features a sectional sofa in soft tones, complemented by a coffee table with decorative items. A large television is mounted on a textured wall, and a dining area with a table and chairs is visible in the background. Natural light enters through expansive glass doors.
Home in Oakton
4.94 out of 5 average rating, 171 reviews

Quiet Luxury Home - Modern - King - 20 Min from DC

Completely new renovations with an eye for details have created a space that feels like a custom built home. Made to provide you with a memorable luxury rental experience. Comfortable, bright, modern, unique and stylishly furnished mastering the mix of timeless elegance and modern simplicity. An open floor plan space that’s equally welcoming and sophisticated, incorporating natural elements, layered fabrics, and textures.

Top guest favourite
Home in Leesburg
5 out of 5 average rating, 136 reviews

Red Watson Mountain House

New modern farmhouse in a private, wooded, but centrally located area where the entire family or several couples can escape for an enjoyable weekend near the acclaimed Virginia Wine Country. Paved parking and super fast WiFi. Minutes from some of the best local Vineyards, Wineries and Breweries. Twenty minutes from downtown Leesburg, historic Middleburg, all less than an hour from Washington DC.

Popular amenities for South Riding holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Loudoun County
  5. South Riding