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Holiday rentals in Hillsboro

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Top-rated holiday rentals in Hillsboro

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Cottage

4.8 out of 5 average rating, 139 reviews

Mountain Top View Spacious Family Cottage

Enjoy beautiful views of the entire Shenandoah valley while relaxing at the Mountain Top Family Cottage. Enjoy great fall colors. Only a 10 min 1/2 mile walk to the Appalachian Trail, where you can hike to historic Harpers Ferry. The cottage features a large living, dining and kitchen area. The master bedroom and the mountain view study provide beautiful Shenandoah valley views. Enjoy the outdoor fire pit and fire circle. Drive to the many historic and recreation areas near Harpers Ferry WV

Guest favourite

Farm stay

4.97 out of 5 average rating, 119 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 favourite

Farm stay

5 out of 5 average rating, 173 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, this structure was built over a natural spring and used for refrigeration. The 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.

Guest favourite

Farm stay

4.93 out of 5 average rating, 379 reviews

Come and get your goat on!

Nestled at the base of the Blue Ridge and tucked away in the woods, we offer a quiet and peaceful get away while being convenient to tons. Enjoy the peace of 13-acres of woodlands and pasture. A large private deck provides a plenty sun with pasture and woodlands views with some great star watching at night. Miles of walking, the Appalachian trail, fantastic cycling; historic towns and places; wineries, breweries, and distilleries; Potomac and Shenandoah rivers. All just minutes away.

Guest favourite

Guest house

4.99 out of 5 average rating, 231 reviews

The Cottage at Dunthorpe Farm

The Cottage is a restored wagon barn nestled against the Blue Ridge Mountains. You'll enjoy quality, comfort, quietude, and pastoral views. We are a fully licensed and inspected B&B on a 1790's farm in rural Loudoun County VA. Each morning you are treated to a continental breakfast of fresh pastry, fruit sourced from local farms, and homemade jams which we quietly deliver by 7:30 unless otherwise requested. Note that the base price is for 1-2 people. Guests 3 and 4 have additional fees.

Guest favourite

Cabin

4.97 out of 5 average rating, 140 reviews

Applemoon: Charming Log Cabin in a Mountain Lake Community

Applemoon is a dog-friendly 1960s log cabin nestled on an acre of the Blue Ridge Mountains. 2 bedrooms with Smart TVs, a porch with hanging daybed and bistro table, and a cozy game loft will give you plenty of space to relax. Outside, enjoy dinner on the huge deck or build a fire and don't forget to look up at the night sky! Applemoon strikes the perfect balance between rustic charm and comfort while maintaining your immersion in the peaceful mountain woodlands of Harpers Ferry.

Guest favourite

Home

4.99 out of 5 average rating, 293 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.

Guest favourite

Tiny home

4.97 out of 5 average rating, 356 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. Guests enjoy private parking & plenty of privacy. Enjoy a remote work getaway, (our broadband is about 8-10Mbps) relax & enjoy LOCO living!

Guest favourite

Guest house

4.81 out of 5 average rating, 266 reviews

Barn Apartment in VA Wine Country

Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged - no satellite, TV, or Internet. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

Guest favourite

Cabin

4.84 out of 5 average rating, 113 reviews

Thousand Acres Of Field

Surround yourself with nature in this modern rustic beautiful cabin in the middle of Loudoun County. Just 15 minutes from town you will feel as if you are miles away from civilization. Please note you will need a 4wheel drive to access and the airbnb app. You will not be able to locate the property without the Airbnb app. We cannot assist you if you do not have the Airbnb app. Please read everything about this beautiful property prior to booking.

Guest favourite

Guest house

4.99 out of 5 average rating, 122 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!

Guest favourite

Cottage

4.97 out of 5 average rating, 119 reviews

Wheatland Spring Farm + Brewery Cottage House

The charm of yesterday with the amenities of today. The private cottage house is appointed with a premium queen size bed, 1.5 baths, and a clothes washer and dryer. The full kitchen includes: oven, stove, microwave, full size refrigerator, dishwasher, and cookware. Guests enjoy scenic views of the 30 acre Wheatland Spring property. A romantic getaway or longer term stay. Just a 100 yard walk from our on-farm brewery.

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Popular amenities for Hillsboro holiday rentals

Free parking on premises

Air conditioning

Stay near Hillsboro's top sights

Hillsborough Vineyards51 locals recommend

Doukénie Winery31 locals recommend

Stoneybrook Farm and Market20 locals recommend

Other great holiday rentals in Hillsboro

Guest favourite

Guest house

4.97 out of 5 average rating, 29 reviews

Wine Country Loft

Guest favourite

Cottage

4.9 out of 5 average rating, 52 reviews

Historic Stone Schoolhouse on Winery Row

Cabin

4.91 out of 5 average rating, 11 reviews

A-Frame Cabin in Harpers Ferry

Guest favourite

Guest suite

4.96 out of 5 average rating, 28 reviews

The Studio @ Shiloh

Guest favourite

Farm stay

5 out of 5 average rating, 53 reviews

Little Round Top Farm - A country getaway!

Cabin

4.87 out of 5 average rating, 69 reviews

~New~Hot Tub~Outdoor Shower~ Fire Pit~10 Acres

Guest favourite

Cabin

5 out of 5 average rating, 25 reviews

Mountainside Retreat: Hot tub,Arcade, Theater,Pets

Guest favourite

Guest suite

4.98 out of 5 average rating, 81 reviews

Tequila Sunset, Harpers Ferry. Entire first floor!

Destinations to explore