Holiday houses in Poolesville

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Top-rated holiday rentals in Poolesville

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Top 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
4.97 out of 5 average rating, 390 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

Top Guest favourite
Cabin in Dickerson
5 out of 5 average rating, 15 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
4.95 out of 5 average rating, 38 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, 32 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 two-story house is surrounded by trees, with warm lights framing the balconies. Large glass windows provide visibility into the interior. A deck with a railing is seen above, and decorative elements are positioned outside the entrance.
Guest suite in Smithsburg
4.98 out of 5 average rating, 314 reviews

Creekside Retreat at the Jewel Vinsota

Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

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
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, 87 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, 159 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
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
4.95 out of 5 average rating, 77 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.

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, 168 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
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 outdoor area features a serene deck framed by greenery. A comfortable seating arrangement is visible under a canopy, along with decorative lighting. Stone pathways lead through the grassy space, where a bird feeder adds charm, inviting natural surroundings into the peaceful retreat.
Guest suite in Herndon
4.95 out of 5 average rating, 317 reviews

Tranquil Sugarland Retreat Close to Airport/Metro

We welcome you to join us and relax in your own private Sugarland guest suite only minutes to the Metro, Dulles Airport, Reston and Ashburn. Enjoy coffee or tea while sitting on a swinging daybed on your private deck surrounded by nature, and then end the night with a peaceful slumber on a luxurious and comfortable King Size bed. Easy off-street parking for one car provided, with ample nearby street parking.

Popular amenities for Poolesville holiday rentals