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Holiday houses in Poolesville

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Top-rated holiday rentals in Poolesville

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

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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, 136 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 private patios and a side yard. Private use of the spacious hot tub with over-sized towels & luxurious robes. Enormous king-size Sleep Number® bed is exceptional. Chef-worthy kitchen and washer/dryer all yours. Free Netflix, YouTubeTV, and Prime; your own thermostat and very fast WiFi. New construction in 2023. Enjoy!

Top Guest favourite
Cabin in Dickerson
5 out of 5 average rating, 16 reviews

Town and Country Getaway (MD-DC-VA)

Situated on 8 acres on MoCo’s Agricultural Reserve, this home is a peaceful oasis with nearby wineries, the Potomac, and C&O canal. This cozy house is fully stocked so you can spend quality time with loved ones, and read on the deck enjoying the wildlife, and take a short drive to Washington D.C., Leesburg, Sugarloaf Mountain, and the Royce Hanson Conservation Park. Enjoy hiking, biking, fishing, casual and fine dining, golf, Lewis Orchards, Homestead Farm, and the Countryside Artisan Studios.

Guest favourite
A spacious living room is highlighted by warm wood flooring and soft overhead lighting. A cozy sofa, accompanied by decorative pillows, faces a media unit. A large artificial Christmas tree stands in the corner, with a few decorative items visible on a nearby shelf.
Home in Boyds
4.92 out of 5 average rating, 39 reviews

Spacious Cozy Suite

This is a very spacious walk-out basement . The kitchen is equipped with an induction cooker, coffee machine, microwave, etc. There is also a washing machine and dryer for your use. The two cozy bedrooms have a queen-size bed and a double bed respectively, and a private bathroom. The bedroom is equipped with a dressing table, sofa, sheets, quilts and pillows. The bathroom is equipped with bath towels, towels, shampoo and shower gel, etc. WiFi and parking are also free. License No.: STR25-00107.

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.
Apartment in Sterling
5 out of 5 average rating, 38 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 exterior of a modern barn features a combination of dark and light siding, with large windows and double doors at the center. A landscaped area with grass and trees surrounds the structure, with a gravel pathway leading to the entrance.
Apartment in Leesburg
4.99 out of 5 average rating, 185 reviews

The Barn at Belgrove

The Barn 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 is located above the barn. It 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 in a rustic environment. There is generally very good cell service but there is no Wifi.

Top Guest favourite
A peaceful outdoor seating area features black Adirondack chairs arranged on a gravel surface. In the background, the white cottage can be seen, framed by lush green shrubs and trees, providing a tranquil setting for relaxation.
Farm stay in Waterford
4.99 out of 5 average rating, 114 reviews

Hope Flower Farm Winery Cottage

Welcome to Hope Flower Farm & Winery! This charming 3-bedroom, 1-bath cottage is the perfect retreat for those seeking a peaceful getaway in the heart of Loudoun County wine country. The cottage features a kitchen, cozy living room, and a screened-in porch perfect for enjoying your morning coffee or an evening glass of wine. The cowboy cauldron is the perfect spot for roasting marshmallows or enjoying a cozy fire. Come experience the beauty and tranquility of Hope Flower Farm & Winery.

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, 93 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, 161 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.

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
4.91 out of 5 average rating, 374 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 treehouse is elevated among the trees, featuring large windows that offer views of the surrounding forest. The exterior is constructed with dark wood shingles and is supported by sturdy stilts, blending seamlessly with the natural environment.
Treehouse in Waterford
5 out of 5 average rating, 226 reviews

Hummingbirds Hideaway Treehouse

Come experience the magic of being among the treetops at our newly built treehouse. Whether you are seeking a romantic getaway, peaceful retreat, or family fun our little slice of heaven will offer you an unforgettable stay. Features large windows for stunning views of the surrounding woods and very detailed woodwork. 2 bedrooms with king beds, open living space with full kitchen and bathroom will be sure to impress. Please Please Please message us prior to booking

Guest favourite
A century-old country house is shown from a distance, framed by expansive green lawns and trees. The structure features a rustic exterior with a red metal roof, a brick chimney, and a large sunroom that opens to the backyard. Scenic hills are visible in the background.
Home in Barnesville
4.98 out of 5 average rating, 47 reviews

The Crooked Camel

Century-old country house in Maryland near the DC metro area. Come relax or enjoy local adventures! Easy access to great cycling, boating, hiking, wineries and breweries, and nature. The house is furnished with interesting decor from 30 years spent overseas. 3 rooms available, sleeping a maximum of 6 adults, and two bathrooms. Nearby MARC train line, visitors should expect to hear passing trains. Manager lives on-property in a separate building.

Top Guest favourite
The living area features a spacious couch dressed in soft blankets, complemented by two armchairs and a dark coffee table. A flat-screen television rests on a media console, while large windows allow natural light to brighten the space, offering views of the surrounding landscape.
Home in Frederick
4.98 out of 5 average rating, 62 reviews

Sugarloaf Mountain Retreat- 300 Acre Estate

Welcome to Sugarloaf Retreat! This cozy one-bedroom, one-bathroom home on a 300-acre estate offers stunning views, a fully equipped chef's kitchen, and a plush king-sized bed. Relax on the patio under the stars after a day of adventure. Conveniently located near Sugarloaf Mountain trails, C&O Canal, golf clubs, roads for biking, and just a short drive from Downtown Frederick, it's the ideal luxury escape in nature.

Popular amenities for Poolesville holiday rentals