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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Guest favourite
The cabin exterior features a blend of rustic log construction and large windows that invite natural light. Surrounded by lush greenery, the spacious deck extends outdoors, adorned with potted plants and a well-manicured lawn, providing a serene outdoor space.
Cabin in Haymarket
4.94 out of 5 average rating, 280 reviews

Lodge on the Lake

A quiet 17 acre, ONE room cabin set on a private small lake, fishing, swimming, and kayaking. Equipped with a full kitchen, a grill, 4 OUT DOOR showers, no showers in cabin. Sleeps 4, 1 QUEEN SIZE BED AND 1 PULL OUT HIDE-ABED. There is a $25/PP per day for extra guests , with prior approval by host. Pet friendly. Cameras are on site. 1 at the parking lot, 1 on the side deck, back deck, covered porch, up stairs open covered card/chest room, 2 on the main dock & water, 1 outside stone patio

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, 112 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.

Superhost
A wooden fence with pointed finials encloses a lush green yard. The gate opens to a garden featuring vibrant plants and shrubs, creating a peaceful outdoor space. Nearby, a small sign indicates a habitat initiative, emphasizing the natural surroundings.
Flat in South Riding
4.91 out of 5 average rating, 43 reviews

Out of Africa

Bedroom and private bath available in beautifully finished basement apartment in quiet neighborhood. Private entrance. Fully furnished; decorated with original African art. The apartment is available long-term for a single, professional guest. We also consider up to 2-wk. stays for 2 guests and 1-wk. for 3 when reservations are made close to stay dates. No animals. We store items in the apartment and consider the kitchen and family room shared space In case we need to access them.

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, 69 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, 165 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
The exterior of a red brick building is shown, featuring a striking peaked roof and multiple windows. A shaded porch is visible at the entrance, adorned with potted plants. Lush greenery surrounds the property, and a gravel path leads up to the structure.
Farm stay in Leesburg
5 out of 5 average rating, 130 reviews

The Forge on Sunnyside Farm

Sunnyside Farm offers a luxurious stay in a beautifully restored historic forge. You’ll be greeted by the farm’s delightful hosts, Jimmy and Dean, two friendly Potbelly pigs. Beautiful cows forage right outside your door. The Forge features exposed wooden beams, brick walls, and cozy furnishings. The interior is designed with plush bedding, a fully equipped kitchen, and spacious living reminiscent of yesteryear. Breweries, wineries and famous antique stores nearby offer entertainment.

Top guest favourite
Farm stay in Aldie
4.98 out of 5 average rating, 125 reviews

Charming Cottage On Horse Farm Middleburg Area

The cottage is set on a beautiful private farm in the center of historic Aldie, Va. and 5 minutes to historic Middleburg. The cottage is surrounded by 11.11 privately fenced acres and is in a very cute setting with a shower and bathroom downstairs along with a kitchen and bedroom upstairs with one queen bed. The apartment accommodates 2 easily with table and chairs inside and on the porch for your comfort. Great opportunity to experience and relax on a small farm in hunt country.

Guest favourite
A serene neighborhood scene captures several residential homes across a well-maintained park area. Soft light glows from warmly lit windows. In the foreground, a grassy green lawn features wooden picnic tables and a basketball court, while a rain-wet street reflects the calming atmosphere.
Guest suite in Aldie
5 out of 5 average rating, 32 reviews

Red Cherry Oasis

Welcome to Red Cherry Oasis. We’re beyond excited to have you! Our home is very special to us. We truly cherish the time and effort that has gone into making this a place where we can come, relax and enjoy. There has truly been a lot of memories created here. Nothing makes us happier than the thought of sharing this amazing space with others like yourself. A traveler searching for cozy conveniences, who just wants to kick back and enjoy a home away from home W∙E∙L∙C∙O∙M∙E!

Top guest favourite
Home in Chantilly
4.92 out of 5 average rating, 37 reviews

Ellipse @ Westfields

Kick back and relax in this calm, stylish space. This 2 Level unit is a new Matisse Model home! Attached 1 Car Garage w/EV Charging Outlet! Enter the light and airy great room, open to the kitchen over a breakfast bar. Upstairs, two large bedrooms open to a hall with a full bath. Your luxurious owner's suite features its own bath with a double bowl vanity. Beautiful LVP Floors all thru Main Level! Minutes to major routes and IAD! Excellence in style, function & location.

Guest favourite
Apartment in Centreville
4.91 out of 5 average rating, 137 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 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, 389 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.

Popular amenities for South Riding holiday rentals

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