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Holiday rentals in Poolesville

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Top-rated holiday rentals in Poolesville

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Guest favourite
A treehouse is elevated among lush greenery, supported by sturdy wooden posts. A small deck extends from the entrance, leading to a spiral staircase. The exterior features dark blue siding and a metal roof, harmonizing with the surrounding forested environment.
Treehouse in Leesburg
4.96 out of 5 average rating, 415 reviews

Romantic Secluded Treehouse Stay in the Sky

Your cell# must match acct! Enjoy sounds of nature and view from our amazing treehouse nestled in the Poplar Trees surrounded by woods. Climb steep spiral staircase to a comfortable modern living area with kitchenette and another spiral staircase to a lovely bedroom with king size bed, bathroom and shower. Enjoy your morning coffee on side deck. During winter months you can see Sugarloaf Mountain in the distance. (Make sure to read the other details to note)booking a treehouse in a tree

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, 270 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 charming red structure is nestled near a tranquil pond, surrounded by lush greenery and flowering plants. A windmill is visible in the background, complementing the rural landscape, while a gravel path leads toward the entrance of the building.
Farm stay in Lovettsville
4.99 out of 5 average rating, 251 reviews

'Waterfront' on 1796 Historic Farm

Feel refreshed when you stay in this rustic gem! The Springhouse is nestled in the rolling hills of Northern Virginia’s Wine Country! Originally constructed in the early 1800's, the structure was built over a natural spring that was used for refrigeration. Water from the spring maintains a constant cool temperature throughout the year while also filling a pond. The original stone well, channel and stone flooring are all intact for guests to explore and experience how our ancestors lived.

Top Guest favourite
An inviting living space features a cozy couch beside a wooden coffee table. Large windows with views of the forest enhance natural light. The kitchen area is equipped with essential appliances, while a rustic wood wall adds warmth to the atmosphere.
Treehouse in Waterford
4.94 out of 5 average rating, 651 reviews

Tranquil Treehouse

Nestled on a hillside overlooking the tributary to the Potomac this glammed out cottage has everything you need for a romantic getaway. Immersed just outside the tall glass walls is a private deck overlooking a forest. This property is from our Waterford reservations collection you might get lucky and see a couple of bald eagles on your visit. Enjoy indoor or outdoor shower. The treehouse is completely private and equipped with wifi, kitchen, king bed fire pit nearby and more. Book smart

Top Guest favourite
A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.
Guest suite in Harpers Ferry
5 out of 5 average rating, 277 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views.

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Top Guest favourite
Tiny home in Reston
5 out of 5 average rating, 145 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, 101 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
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, 166 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.

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
4.91 out of 5 average rating, 382 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.

Top Guest favourite
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.
Home in Purcellville
4.99 out of 5 average rating, 332 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.

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, 180 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 Quarters at Belgrove is showcased, featuring a charming white facade with decorative paneling. Two large garage doors and a welcoming entrance are visible, complemented by planters filled with vibrant flowers. Natural greenery surrounds the property, enhancing its serene setting.
Apartment in Leesburg
5 out of 5 average rating, 210 reviews

The Quarters at Belgrove

The Quarters at Belgrove. Welcome to a private and quiet escape on a 67 acre manor in Leesburg. A horse property with abundant wildlife offers a peaceful getaway on an historic property. This full apartment with separate entrance is convenient to downtown Leesburg, Morven Park, and Loudoun's many wineries, breweries and festivals. Most suitable for adults seeking to relax, recharge, and rekindle. There is generally very good cell service but there is no Wifi.

Popular amenities for Poolesville holiday rentals