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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
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, 45 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.

Guest favourite
Home in Sterling
4.86 out of 5 average rating, 79 reviews

Private Basement near Airport (9 mins)

Enjoy a charming basement suite with a private entrance, queen-size bed with fresh sheets, a full bathroom, TV, and air conditioning. The kitchenette includes a coffee maker, coffee, sugar, microwave, mini fridge, and basic utensils. Relax in the backyard, ideal for morning coffee. Located near Dulles Airport, One Loudoun nightlife, and Northern Virginia wineries. Guests have private access and on-site parking. We respect your privacy but are available for assistance. Book now for a comfy stay!

Top Guest favourite
A well-appointed queen bedroom is highlighted by a sturdy metal bed frame and soft linens. A neatly folded set of towels is placed on the bed. A wooden dresser and a TV are positioned opposite the bed, while built-in closets provide additional storage.
Apartment in Leesburg
5 out of 5 average rating, 9 reviews

Cozy 2BR suite in Leesburg, VA

Welcome to your peaceful retreat in charming Leesburg, Virginia ideal for families, friends, or professionals seeking comfort, convenience, and space to unwind. This modern, private home features two beautifully furnished queen bedrooms and a full kitchen perfect for extended stays or quick getaways. What You’ll Love: - 2 queen bedrooms w/ soft linens & restful - Kitchen w/ fridge, oven, microwave, and airfryer - Free on street parking - Spa like shower with essentials - Washer & Dryer onsite

Top Guest favourite
A bright and open living space features a striped sofa with a wooden coffee table and decorative wicker baskets. A dining area with modern chairs is complemented by a patterned wall art piece. Natural light streams in from the doorway, enhancing the inviting atmosphere.
Guesthouse in Herndon
4.94 out of 5 average rating, 140 reviews

Modern Sugarland Apt-Metro/IAD

Welcome to our stylish basement apartment, perfect for modern travelers. Whether you're here for work or leisure, this space has you covered. Situated minutes from the Metro, Airport, and major work centers. The apartment features a desk with dual monitors, keyboard, mouse, and 1GB internet. At night, relax in the plush king-size bed. A convertible futon couch with a 65-inch TV, awaits your binge-watching sessions. A washer/dryer and full kitchen, w/refrigerator and stove complete the space.

Top Guest favourite
A bright bedroom features rustic wooden walls with horizontal stripes, complemented by large windows bringing in natural light. A spacious bed with white linens is paired with decorative pillows. A dresser and bedside table are positioned nearby, along with a fan for added comfort.
Cabin in Leesburg
4.95 out of 5 average rating, 21 reviews

Cabin On Fern Ridge

Escape to our newly renovated stylish 2-bedroom cabin in DC’s Wine Country, Cabin On Fern Ridge is a Waterford Reservations Elite Property Perfect for couples, families or solo retreat, it blends modern comfort with rustic charm. Enjoy private wooded property, king size beds, and a fully equipped kitchen. Relax on the fenced stone patio with outdoor fireplace. Cabin is ideal for visiting the areas best attractions wineries, breweries, hiking and more or simply unwinding in nature's embrace.

Top Guest favourite
An open living space features a modern seating area with a brown leather sofa and two patterned ottomans. A small table with bar stools stands against the wall, complemented by a kitchenette area. A flat-screen TV is mounted nearby, with a door leading to the outdoors.
Guest suite in Leesburg
4.97 out of 5 average rating, 67 reviews

The Studio @ Shiloh

**The Studio @ Shiloh sits on a park-like estate. Originally a garage, The Studio has been NEWLY REMODELED. Enjoy beautiful views with rolling hills, ponds, and lush green landscaping. Come stay and refresh your soul in our peaceful studio apartment or GO and have fun! Convenient to breweries, wineries, C&O Canal for biking or hiking, and antique shopping at the popular Lucketts Store. 11 miles south to historic downtown Leesburg, Virginia or 15 miles north to historic Frederick, Maryland.**

Top Guest favourite
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
4.96 out of 5 average rating, 71 reviews

Gorgeous cabin on Blue Ridge

Atop the Blue Ridge close to Harper’s Ferry and Virginia wine country this airy retreat overlooks the idyllic Shenandoah. Our two-person soaking tub on a magnificent deck, huge firepit, gorgeous vintage interior, grand piano, and warm pine ceiling and floors, give you the perfect place to get away from city life for a bit. Full kitchen. Two bedrooms plus a big couch that could sleep someone else in a pinch, and a cozy little fireplace top it all off! Just steps to the Appalachian Trail.

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, 186 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 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, 164 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
Guesthouse in Sterling
4.91 out of 5 average rating, 81 reviews

Bright Cozy Guesthouse in Sterling

Forget your worries in this spacious and serene space. Plenty of sunlight and perfect for a weekend gateway. Come enjoy this cozy private guesthouse located adjacent to our house with all the amenities necessary to enjoy your stay. Guesthouse situated on private property with 30 min + drive to exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round Hill. Recharge in a peaceful setting.  Adults Only. No pets.

Popular amenities for Poolesville holiday rentals