Vacation rentals in Poolesville

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Top-rated vacation rentals in Poolesville

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Top guest favorite

A tranquil pool area is surrounded by lush greenery and vibrant flowers. The charming cottage, featuring a welcoming porch, is visible in the background under a bright blue sky. The clear water of the pool reflects the sunlight, inviting relaxation.

Cottage in Hamilton

4.95 out of 5 average rating, 398 reviews

*Cottage @ Firefly Cellars* VA Wine Country escape

The Cottage at Firefly Cellars is a private, tranquil escape on the tasting room property. Come enjoy the private pool (in summer months), walk the property with a glass of wine, enjoy views of the neighboring horses, hop to local wineries, or just sit back and enjoy all the cottage has to offer. The cottage is meticulously maintained, beautifully designed, and you will feel at home the moment you walk through the doors. Perfect for a couple, or an individual looking to escape from busy life!

Guest favorite

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

4.94 out of 5 average rating, 32 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 favorite

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, 17 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 favorite

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

4.92 out of 5 average rating, 119 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 favorite

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, 178 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 favorite

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, 73 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 favorite

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, 149 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.

A serene bedroom within the dome features a spacious bed adorned with soft white linens and blue accent pillows. Large windows provide views of the surrounding greenery, while a comfortable chair and a hanging hammock offer cozy relaxation options. A woven rug adds warmth to the area.

Dome in Leesburg

4.82 out of 5 average rating, 136 reviews

Luxe & Picturesque Dome Haven ~ Hot Tub ~ Glamping

Experience Luxury Glamping in Leesburg! Discover the perfect blend of comfort and nature in our charming dome, just minutes from downtown Leesburg. Enjoy modern amenities like split AC/heating, WiFi, a projector, fridge, and coffee maker. Relax in the outdoor jacuzzi, cozy up by the propane fire pit, and unwind under ambient lighting. Explore renowned wineries, Morven Park, and local attractions nearby. A unique, romantic escape awaits—book your unforgettable glamping getaway today!

Top guest favorite

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, 155 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!

Guest favorite

A charming French farmhouse exterior is showcased, featuring a white facade and a welcoming entrance. The circular driveway is lined with well-maintained shrubbery and flower beds. Lush greenery surrounds the property, and a clear blue sky is visible above.

Home in Beallsville

4.95 out of 5 average rating, 21 reviews

The barn a French Farm House.

This beautiful Barn French farm house Embark on an off grid adventure this 3 bedroom 2.5 bathroom in Beallsville (1) to town of Poolesville nestle on 20 acres of secluded bills this French farm house luxury through the property 3- fireplaces. THE LOCATION: FOUR STREAM GOLF COURSE,THE CROSS VINEYARD, POOLESVILLE GOLF COURSE,4- WINERIES THE AREA, ROCKLAND, BLUE FROG, WINDRIDGE, HAND MAD BREWING, MARKET LOCAL CAFE AND MARKET, BUTTLER ORCHARD, LEWIS ORCHARD.

Top guest favorite

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, 44 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 favorite

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, 447 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.