House holiday rentals in Leesburg

4.99 out of 5 average rating, 122 reviews

A stone fireplace is centered in a rustic setting, featuring a stylish wrought iron screen. Flickering flames are visible, surrounded by two red lanterns and a glass of red wine beside an open bottle, creating a cozy ambiance for relaxing evenings.

Home in Marshall

Middleburg/Upperville-Stunning,renovated cottage

The Atoka House,a stunning 1801 log home on the historic register in Virginia hunt country.This 2-bedroom, 2.5 bath home with both upstairs and downstairs living rooms,is only 4 miles from Middleburg.Relax in the coziness of the log cabin, catch the spectacular sunsets from the deck and large fenced yard. Gas grill and outdoor firepit. Fireplace may only be used with a duraflame log(provided) for the safety of this historic home. Minutes from wineries, great meadow, polo and Upperville (UCHS)

A bright living area features a comfortable cream-colored sofa adorned with patterned cushions. A round dining table with yellow chairs occupies the space, accompanied by a decorative basket. A large television is mounted on the wall, enhancing the room's modern feel.

4.97 out of 5 average rating, 153 reviews

Leesburg Hideaway w/ King Bed + Private Backyard

Escape to this light-filled two bedroom, one bathroom bungalow located minutes from the heart of Leesburg's historic district. Just a short drive from unique shops, restaurants, and outdoor activities. This is the perfect home base whether you're in town for a weekend getaway or an extended stay. Located near the W&OD Bike Trail, Birkby House, Morven Park, breweries, wineries,and Rust Manor. We're excited to host you in our little slice of Leesburg charm! Bikes included: 1 mtn. & 1 cruiser

4.96 out of 5 average rating, 112 reviews

A well-appointed living area features a spacious sectional sofa and an adjoining dining space. Large windows allow natural light to illuminate the room, creating a bright atmosphere. The kitchen is visible in the background, featuring high-end appliances and modern design elements.

Home in Sterling

The Villa on Lakeside

The Villa is a stunning single-level residence with a half-acre fenced yard. Your entire family, including your beloved furr babies, is warmly welcomed here. The villa features 3 bedrooms and two newly renovated bathrooms, each boasting heated bidet toilet seats. For remote workers, the office is equipped with a wireless printer and a phone. The kitchen is designed with high-end appliances, including a built-in coffee maker. Additionally, a full laundry room is available for your convenience.

4.96 out of 5 average rating, 106 reviews

A spacious basement area is shown, featuring a large, comfortable couch arranged around a coffee table. An exercise treadmill is positioned nearby. A ping pong table adds activity options, while windows provide natural light. The decor includes framed artwork on the walls.

Home in Bristow

Big Basement in Bristow, VA

Spacious private basement just minutes from Jiffy Lube Live, 30 miles from D.C., and an hour from Shenandoah. Nearby, enjoy movie theaters and great restaurants. The basement features a private entrance, cozy bed, couches, a private bathroom, a kitchenette with a microwave and fridge (no kitchen sink, stove, or oven), plus a game/exercise area. Whether you're unwinding after a concert, watching TV, playing games, or working out, this space offers comfort and convenience for a relaxing stay.

4.99 out of 5 average rating, 103 reviews

A well-lit bedroom features a vintage white metal bed frame with a soft gray blanket and pillows. A wooden dresser and a mirror are positioned beside a rocking chair, while two bedside lamps provide warm illumination. Light flows through the window, flanked by sheer curtains.

Home in Ashburn

Ashburn Manor: 1920’s Farmhouse

Take advantage of this unique opportunity to stay in a beautiful,historic home right in the heart of old Ashburn. Just a quarter mile from the W&OD bike trail, walking distance to several shops/restaurants, 10 min. from Dulles Airport and the metro (easy access to DC), and at the edge of Loudoun County’s vast wine region. The home has been updated with all modern amenities for your comfort. Enjoy BBQ on the patio, books on the sun porch, or coffee on the deck. Peace and serenity await.

4.97 out of 5 average rating, 267 reviews

The entrance to The Crooked Cottage is framed by wooden planks and surrounded by greenery. Two windows offer glimpses into the inviting interior, while a gravel pathway leads up to the door, playfully adorned with a sign featuring the name of the cottage.

Home in Myersville

The Crooked Cottage: a Cozy, Curated Escape

You will instantly relax in this stylish, pet-friendly home only 8 mins from I-70, exit 42. Under a canopy of trees find a beautifully landscaped yard with decks and two fire pit areas. Enjoy the well-apportioned kitchen with organic, fair trade coffee. Relax with 2 Roku TVs, games and puzzles, bathe with soaking salts and Turkish towels. For outdoor enthusiasts, pitch your tents. Sit by the wood-stove in the winter, or lay in a hammock when it’s warm. Welcome to The Crooked Cottage!

A spacious sitting room features hardwood flooring and large windows allowing natural light. A stone fireplace serves as a focal point, complemented by built-in shelving. A dark sofa with decorative pillows and an accent chair enhance the cozy ambiance, while a patterned rug adds texture.

4.97 out of 5 average rating, 181 reviews

WILD HARE COTTAGE king bed

Perfect for exploring wine country we are 10 minutes from Bluemont Station and Dirt Farm Brewing This property has two bedrooms King and Queen beautiful bathroom in the middle. The kitchen perfectly sized to gather four people. large sitting room out front. Sit on the front porch and watch the travelers pass by on the gravel road. Walk up to the historic Philomont store. Please note this cottage is attached to the front of the main house it’s completely separate utilites and all

The farmhouse is set on a spacious green lawn, surrounded by tall trees. A nearby structure with a cylindrical silo complements the main house, which features a blue-green roof and a wide porch. A bright sky with scattered clouds enhances the serene landscape.

4.99 out of 5 average rating, 327 reviews

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

4.99 out of 5 average rating, 174 reviews

The kitchen features exposed brick walls and wooden beams, creating a rustic ambiance. A large wooden dining table is surrounded by chairs, with a bowl of fruit at its center. Vintage appliances and a farmhouse sink complement the warm, inviting atmosphere.

Home in Waterford

Restored 1820 Waterford Village Farmhouse

We restored this 1820 village farmhouse in 2016. It is situated in the heart of the historic village of Waterford. It has 2 1/2 acres behind, with two barns, a herd of very friendly goats, chickens, and vegetable, herb and flower gardens. The house backs up to The Phillips Farm, 150 acres of preserved land and public walking trails. Beautiful sunset views from the back porch. The house, a work in progress, was featured in both Country Living and Preservation Magazines.

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.

5 out of 5 average rating, 169 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!

The exterior of a two-story historic home features clapboard siding painted in light blue. A red door stands at the center, flanked by white shutters. An American flag is displayed next to the entrance, while a brick pathway leads to the front steps.

4.98 out of 5 average rating, 103 reviews

Historic home in the heart of downtown Leesburg!

This 1800s historic home is located in the heart of downtown Leesburg. The “Leesburg Bookstore” was renovated with updated amenities that make for the perfect getaway. A hidden gem, it is walking distance to breweries, restaurants, antiques, shopping, and more! The charms of Leesburg and surrounding areas are easily accessible, including the Northern VA Wine trail, W&OD walking/biking trail, DC, MD, and beautiful drives through scenic horse country.

A bright living space features a cozy couch and an accent chair, positioned near a wall-mounted flat-screen TV. A dining area with a rustic wooden table and decorative placemats complements the room. A vibrant wall art piece adds character, along with a green plant wall.

4.97 out of 5 average rating, 114 reviews

Quaint Royal Cottage @ Historic Leesburg

Welcome to the Quaint Royal Cottage, a beautifully appointed home nestled in one of Historic Leesburg's most desirable neighborhoods. Just a short stroll away, you'll find an array of dining options ranging from gourmet restaurants to casual eateries, along with numerous brewpubs and vibrant nightlife spots. After a night out, retreat to the serene backyard oasis and relax by the fire pit. Your delightful stay is guaranteed!

Popular amenities for Leesburg house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.94 out of 5 average rating, 141 reviews

A spacious mountain home is set against a backdrop of trees, with a gently sloping field leading to a small pond in the foreground. A wooden fence encircles the property, highlighting the serene outdoor environment that encompasses the house.

Home in Sabillasville

Stoney Spring Overlook

4.88 out of 5 average rating, 216 reviews

A spacious backyard is surrounded by a wooden fence, showcasing a patio area with multiple seating options. A hot tub is visible, along with a fire pit and several Adirondack chairs arranged for gathering. Lush green grass and mature trees enhance the outdoor setting.

Home in Harpers Ferry

The Historic Booth House at the Harpers Ferry KOA

5 out of 5 average rating, 110 reviews

A circular fire pit is surrounded by six gray Adirondack chairs, set on gravel. Beyond, a spacious wooden deck is visible, featuring a covered area and a picnic table. The yard is fenced with trees providing a natural backdrop.

Home in Hedgesville

Spacious & Charming! Large deck+Game shed+Firepit

4.97 out of 5 average rating, 208 reviews

The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.

Home in Harpers Ferry

Historic Farmhouse w/ Heated Pool, Harpers Ferry

4.93 out of 5 average rating, 117 reviews

A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.

Home in Marshall

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

4.76 out of 5 average rating, 288 reviews

An aerial view showcases the nine-acre estate featuring a charming stone house, surrounded by vibrant fall foliage. The swimming pool is visible adjacent to a patio area, with a gazebo nearby. The spacious driveway accommodates several vehicles, enhancing accessibility.

Home in Strasburg

Cedar Creek Wayside Castle

4.94 out of 5 average rating, 112 reviews

A landscaped backyard features a patio table with an orange umbrella and four chairs. Sunlight filters through the trees, illuminating the area. A path leads to a wooded setting, with autumn leaves scattered on the ground, creating a serene atmosphere.

Home in Reston

Nature Zen *Metro Walk *Visit DC *Relaxing Lakes

5 out of 5 average rating, 100 reviews

A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

Weekly house rentals

The modern kitchen features sleek white cabinetry and a spacious island with four leather bar stools. State-of-the-art appliances include a refrigerator and built-in microwave. Natural light floods in from a nearby sliding glass door, creating a bright and inviting cooking environment.

5 out of 5 average rating, 25 reviews

South Street Stay - Downtown Leesburg

5 out of 5 average rating, 16 reviews

Home in Lovettsville

The Dutchmans Creek Farmhouse

4.97 out of 5 average rating, 58 reviews

A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

A spacious cabin is set against the backdrop of lush hills, featuring large windows that fill the interior with natural light. A wide deck with black railing wraps around the front, providing an inviting space to enjoy the outdoor views.

4.94 out of 5 average rating, 34 reviews

The Cabin at Blue Valley Farm

A charming cottage is set amidst lush greenery, featuring a welcoming porch with white railings. Red shutters frame the windows, while vibrant landscaping with shrubs and trees enhances the exterior. The blend of wood and stone elements adds to the cottage's rustic appeal.

4.98 out of 5 average rating, 62 reviews

The Cottage at Oakland Green Farm

4.83 out of 5 average rating, 120 reviews

An open-concept living space showcases a brown leather sofa and a dining area with a wood table. A billiards table is positioned in the center, with overhead lighting illuminating the room. Large windows are adorned with sheer curtains, allowing natural light to fill the space.

Home in Sterling Park

Stylish & Spacious House by Dulles Airport

4.96 out of 5 average rating, 45 reviews

The exterior of a Scandinavian-inspired retreat is framed by trees displaying autumn foliage. A modern metal roof complements the natural wood siding. Soft lighting from the entrance enhances the inviting ambiance as the sun sets in the background.

Home in Sharpsburg

Nature Escape Walk to C&O Towpath & Potomac River

4.85 out of 5 average rating, 75 reviews

Home in Sterling

Private Basement near Airport (9 mins)

Private house rentals

Home in Round Hill Village

The exterior of a two-story farmhouse is presented, featuring a white façade and a welcoming front porch. A classic brick chimney adds character, while a well-maintained lawn and brick pathway lead to the entrance. Surrounding trees create a serene atmosphere, enhancing the property’s natural charm.

4.97 out of 5 average rating, 70 reviews

Historic Farmhouse, Fully Renovated in Fall 2023

Sunset colors reflect in windows that are adorned with wooden shutters. Flower boxes filled with purple blossoms enhance the exterior, while stone path leads to the entrance, framed by flourishing greenery beyond.

4.96 out of 5 average rating, 76 reviews

Retreat in Downtown Leesburg

5 out of 5 average rating, 5 reviews

Home in Herndon

Cozy 2bd/ba Private Above Ground First Floor Suite

5 out of 5 average rating, 45 reviews

A historic stone house stands in a serene rural setting. A gravel driveway winds up to the home's entrance, surrounded by gently sloping green grass and sparse trees. Nearby fields stretch into the distance, under a clear blue sky with scattered clouds.

Home in Waterford

The Spring House, Farm Stay

Home in Round Hill Village

The charming exterior of a two-story house features a classic design with a metal roof and white siding. The front porch is adorned with seating arrangements, while large windows are framed by wooden shutters. Stone walkways guide visitors to the welcoming front door.

4.96 out of 5 average rating, 82 reviews

Location, Location, Location in Round Hill, VA

Superhost

A spacious great room is highlighted by a stone fireplace. Large windows allow for views of the surrounding nature. A comfortable sofa and chairs are arranged with soft blankets, and a sleek black table adds functionality to the inviting space.

4.75 out of 5 average rating, 20 reviews

Artist Retreat

Superhost

The exterior of a spacious, modern log cabin home is showcased, featuring a large covered porch and multiple gabled roofs. The surrounding landscape includes an expansive grassy area and trees, with a clear blue sky overhead.

4.77 out of 5 average rating, 13 reviews

Modern Barndominium. 5 BR. Sauna. Firepit. 11 acre