Vacation rentals in Hillsboro

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Top-rated vacation rentals in Hillsboro

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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!

Top guest favorite

A bright living area is presented with large windows allowing natural light to fill the space. Comfortable furnishings include a sectional sofa and a circular coffee table, while a patterned area rug adds warmth. A television is mounted on a dark cabinet, enhancing the room's functionality.

Farm stay in Purcellville

4.98 out of 5 average rating, 146 reviews

50-Acre Farmhouse Getaway Oasis in VA Wine Country

Just 1 hour from Washington DC, the spacious and tranquil Farmhouse at Dogwood Pond resides on 50 acres of land, and includes a large pond equipped for fishing. Our guests enjoy the nearby Purcellville Historic District for quality restaurants and cafes, vintage shopping, and the W&OD trail entrance at the old Purcellville train station. The property is also a swift 20 minute drive to historic downtown Leesburg, Waterford, Harper's Ferry, and endless wineries, breweries, hiking and bike trails.

Guest favorite

A cozy living space features exposed wooden beams on the ceiling, a comfortable sectional sofa, and a wooden coffee table. Large windows provide views of the surrounding landscape, while a television is positioned on a rustic entertainment console. The room is inviting for relaxation and socializing.

Farm stay in Hillsboro

4.95 out of 5 average rating, 202 reviews

Homestead 1870 in Wine Country

This cozy two-bedroom rustic farmhouse nestled in Virginia’s wine country and part of a working farm where guests can see farm animals. Close to local wineries, breweries, and delicious food. Located near Harper’s Ferry, the Appalachian Trail, and the Potomac River, perfect for hiking, kayaking, and exploring. Adventure parks and scenic trails are nearby, offering plenty of activities. Relax and enjoy farm life, local charm, and the beauty of Virginia's countryside from a well centered location.

Guest favorite

A cozy tiny home is surrounded by lush greenery. Outdoor seating is provided with a small table and chairs, while planters filled with flowers enhance the space. A soaking tub is visible on the patio, adding to the charm of the outdoor area.

Tiny home in Harpers Ferry

4.96 out of 5 average rating, 150 reviews

Enchanting PET FREE W/Amazing ViewHot Tub Overlook

Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Featuring large patio, outdoor dining area, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" outdoor soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Top guest favorite

An outdoor seating area is set in a grassy space, featuring weathered chairs arranged around a stone fire pit. A wooden picnic table is visible, surrounded by lush greenery and trees. The backdrop reveals a scenic view of the rolling hills under a partly cloudy sky.

Cabin in Bluemont

4.99 out of 5 average rating, 563 reviews

Rustic Blue Ridge Cabins

Quaint Rustic Cabin nested at the top of the Blue Ridge Mountains w/detached 150 ft² bedroom Cabin, located in the heart of Western Loudoun Wine Country. Sitting on 1/3rd of an Acre with access to wooded a trail featuring Cold Springs. Amenities-4 person hot tub, beautiful view of the Loudoun Valley, Wifi, Loft bedroom with a loft ladder, hiking along the Appalachian Trail,Shenandoah River, with restaurants, breweries, distilleries, and wineries close by! These are rustic not luxurious Cabins

Top guest favorite

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, 229 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 favorite

The exterior of the home is showcased at dusk, highlighting its wooden façade and large windows. Warm outdoor lights create a welcoming atmosphere. A spacious deck with steps leads to the entrance, surrounded by wooded terrain, indicating a private and serene location.

Guest suite in Harpers Ferry

4.98 out of 5 average rating, 128 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Welcome to Tequila Sunset in Harpers Ferry, WV! This beautiful, secluded home has stunning sunset views, you'll truly feel on top of the world! 100 mile vista of the gorgeous Blue Ridge Mountains. Entire first floor is yours, no shared spaces! Over 1200 SF of room to unplug & relax. King size Nectar bed, cozy indoor wood burning fireplace, outdoor firepit, 84" TV, & a private deck to enjoy the natural surroundings. Just 2 miles from the renowned Mountain Lake Club and the Appalachian Trail!

Top guest favorite

A scenic outdoor view showcases a wooden deck winding down to a lush landscape. Vibrant flowers and greenery adorn the space, while a hot tub is visible nearby. A beautiful sunset casts warm hues across the sky, offering panoramic views of the valley below.

Guest suite in Harpers Ferry

5 out of 5 average rating, 263 reviews

Luxury Mountain Getaway: Sunsets, Wines & Views.

Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Top guest favorite

The farmhouse is set on a spacious green lawn, surrounded by tall trees. A nearby structure with a cylindrical silo complements the main house, which features a blue-green roof and a wide porch. A bright sky with scattered clouds enhances the serene landscape.

Home in Purcellville

4.99 out of 5 average rating, 322 reviews

Whole House -Seven Elms Farm B&B

Come and enjoy peaceful setting of our 1870 farmhouse situated close to historical Town of Purcellville, great for shopping and enjoying a good meal, W&OD trail is nearby for a walk or a jog. Or you can just sit on either one of the two covered porches with a good book and take in natural open spaces and a view of a serene pond. And of course we are located in heart of Loudoun County's wine country, great spots for picnic and tasting of great selection of wines.

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, 201 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 exterior of a charming tiny home is displayed, featuring natural wooden siding and a metal roof. A small porch with wooden steps leads to a glass-paned front door. Potted plants adorn the entrance, while colorful flowering bushes are visible in the foreground.

Tiny home in Purcellville

4.97 out of 5 average rating, 419 reviews

Tiny House near Purcellville

Nestled in the heart of Purcellville is a tiny home with a ton of charm. Less than 5 miles from vineyards, LOCO ale trail breweries, cideries, WO&D bike trail & 20 min to historic Leesburg, the Shenandoah river & Appalachian Trail. Our tiny house is a bit larger w/ 2 bedrooms, full kitchen & bath, family room & cozy front porch with private parking. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Top guest favorite

The bright bedroom features a spacious bed with crisp white linens and a light gray throw. A comfortable armchair is positioned beside a side table, with natural light flooding in through large windows framed by light gray walls.

Guesthouse in Lovettsville

4.99 out of 5 average rating, 149 reviews

Modern dreamy mountain view oasis in wine country

Right in the heart of Loudoun County's wine, beer and equestrian country. If you are looking for an outdoor getaway with access to the Ap Trail, biking, kayaking, etc., here for the wine and beer or simply for a change of scenery, this is the place for you. Watch the sun go down right from your bed or, "The Meadow" with the Blue Ridge Mountains as your backdrop. Slowly sip coffee or tea from the hammock, it's up to you. Book now!