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 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, 246 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 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, 66 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
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, 639 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
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, 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.

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, 377 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
A dining area features a glass-top table surrounded by four chairs, with two in dark blue upholstery. A black cabinet displays decorative items, while a plush area rug adds texture to the beige carpet. Two framed art pieces brighten the space with color.
Apartment in Great Falls
4.96 out of 5 average rating, 90 reviews

Wooded Retreat in Great Falls

Escape to this wooded retreat in Great Falls, perfect for nature lovers and adventure seekers. This basement apartment boasts a dining area with sunlit windows showcasing vibrant forest views, a spacious living room, and a cozy bedroom. Enjoy easy access to hiking, biking, and outdoor fun in the parks just minutes away. Relax in the great outdoors experience the shops and dining in the nearby village. A perfect blend of nature and adventure awaits at this charming getaway.

Guest favourite
The exterior of a historic farmhouse features a yellow wooden facade and a red roof. Lush green grass surrounds the house, with vibrant flower beds showcasing blooming irises and other plants. A spacious outdoor area offers a clear view of the beautiful landscape.
Home in Boyds
4.9 out of 5 average rating, 29 reviews

Honey Acres Farm House

Relax in our historic 18th century farm house. With charming views of a pond, fields of grazing horses, and wildlife all around. Enjoy the well lit great room, the cozy living room, or the spacious patio. Dive into nature with hiking trails through Seneca Creek, an rural winery, and three local orchards and farmers markets, all just minutes away, or engage with the local culture in Baltimore and DC, just a 45 minute drive away. Choose something unique for your getaway!

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, 49 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
A spacious room features a custom wood bed with light bedding and natural elements. The wooden ceiling beams provide an open feel, while soft light enters through multiple windows. A cozy sitting area includes a couch and side tables, enhancing the peaceful ambiance.
Cottage in Leesburg
4.92 out of 5 average rating, 458 reviews

Romantic Stone Cottage Circa 1869-75 acres to Hike

Plan a relaxing getaway at our Stone Cottage, just 15 minutes from Leesburg and under 90 minutes from D.C. Nestled next to a hidden state park with peaceful walking trail, this hilltop retreat offers both seclusion and convenience. Enjoy a custom king bed, inviting interior, and close to many top wineries, breweries, and restaurants. Whether you're here for a wedding, wine tasting, or quiet escape, the Stone Cottage is your perfect getaway.

Popular amenities for Poolesville holiday rentals