Vacation rentals in Dickerson

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Top-rated vacation rentals in Dickerson

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Guest favorite
The kitchen area features a warm wood design with open shelving displaying plates and glasses. A stainless steel sink is accompanied by a dishwasher and a countertop appliance arrangement, including an air fryer and coffee maker. Soft lighting enhances the inviting layout.
Guesthouse in Lovettsville
4.91 out of 5 average rating, 210 reviews

The Patent House

Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen) & full bath upstairs. There is a convertible sofa downstairs (full). Cabin is next door to our house & shares a fence with our pasture where our mini donkeys live. We have yappy dogs and friendly outdoor cats. We're in the country, so bugs make their appearance but they tend to go straight to the window sills.

Guest favorite
The exterior of a spacious, modern log cabin home is showcased, featuring a large covered porch and multiple gabled roofs. The surrounding landscape includes an expansive grassy area and trees, with a clear blue sky overhead.
Home in Leesburg
4.91 out of 5 average rating, 11 reviews

Modern Barndominium. 5 BR. Sauna. Firepit. 11 acre

Bring the whole family to this great place with lots of room for fun. Lots of amenities like Jacuzzi, Sauna, firepit, backyard pond, Shuffle board, indoor basketball, and lots of other games like giant connect four, cornhole, chess, giant jenga, and others. Archery and Axe throwing is an added amenity for an extra fee. If interested please ask. Jacuzzi will not be operating in the winter months December to February. There is a working distillery on site. It will not interrupt the stay at all.

Guest favorite
A mid-century cabin is set amidst lush greenery, showcasing a well-maintained lawn highlighted with blooming flowers. Towering trees provide shade, while the home’s light yellow exterior contrasts beautifully with the natural surroundings. A vehicle is parked nearby, indicating convenient access.
Cabin in Dickerson
5 out of 5 average rating, 10 reviews

Town and Country Getaway (MD-DC-VA)

Get away from it all and relax at our quiet, charming cabin. Situated on 8 acres in MD’s Agricultural Reserve, this countryside escape is a short drive or Metro ride from the attractions of Washington D.C., near Sugarloaf Mountain, the Royce Hanson Conservation Park, the C&O Canal, and the Potomac River. Enjoy hiking, biking, fishing, wineries, casual and fine dining, golf, and the local arts of Poolesville, MD. and Countryside Artisans Studio Tours. * 45 mins. drive to Leesburg, VA.

Guest favorite
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, 106 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 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, 75 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, 150 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 favorite
A relaxing bedroom features a spacious bed covered in blue and white linens, accented by pillows in warm tones. Framed landscape artwork hangs above the bed, while bedside tables with lamps provide soft lighting. A doorway leads to a bathroom.
Apartment in Leesburg
5 out of 5 average rating, 11 reviews

Eagle’s Rest | King Bed | Wine Country Apartment

Perched in a peaceful setting surrounded by nature, Eagle’s Rest offers a tranquil escape where comfort meets the wild. Inspired by the majesty of the eagle, this bird-themed hideaway invites you to slow down, breathe deep, and enjoy nature, rustic charm, and thoughtful details throughout. Whether you're a bird lover, a couple looking for a romantic getaway, or a solo traveler seeking solitude, you’ll find it easy to unwind in this cozy, stylish space designed for rest and renewal.

Top guest favorite
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, 203 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

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, 158 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 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, 46 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 winding pathway made of pavers is bordered by lush greenery, including large leaves and blooming hydrangeas. The pathway leads through a garden, creating a natural and inviting entrance to the property.
Guest suite in Leesburg
4.99 out of 5 average rating, 224 reviews

Suite GG ~ Relax & Enjoy

Let this cozy above-garage apartment be your home away from home. Located in Lucketts, VA we are within a short distance to the small artsy town of Leesburg, local wineries, breweries, antique stores, shopping outlets, hiking, biking and canoeing/kayaking on the Potomac River. Our spacious, fully-furnished apartment with private entrance sits above a detached garage and features a lovely raised deck overlooking the back gardens.

Top guest favorite
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, 56 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.

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