Holiday rentals in Round Hill

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Top-rated holiday rentals in Round Hill

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Guest favourite

Cabin in Bluemont

4.98 out of 5 average rating, 451 reviews

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, located in the heart of Western Loudoun Wine Country. Sitting on over 1/3rd of an Acre for you to enjoy. Amenities include a 4-person hot tub, a beautiful view of Loudoun Valley, wifi access, has a loft bedroom with a loft ladder, and hiking along the Appalachian Trail. Close to the Shenandoah River, assortment of restaurants, breweries, distilleries, and wineries in the surrounding area. This is a rustic not luxurious cabin!

Guest favourite

Farm stay in Purcellville

4.97 out of 5 average rating, 106 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 in Round Hill

4.98 out of 5 average rating, 235 reviews

The Log Cabin at Historic Oak Hill Farm

Please read carefully before booking: The Log Cabin at Oak Hill Farm to 1790 and was the ancestral home of the Lodge family who came to Loudoun County in the 1700s from Chester County, PA. Oak Hill is featured as a historical site in Eugene Scheel's historical map (1997) and is still a working farm. Due to the age of the cabin, the full bathroom is on the lower level and may not work for all guests. In addition WIFI is spotty. To preserve the experience at Oak Hill, we do not accept pets.

Guest favourite

Farm stay in Round Hill

4.93 out of 5 average rating, 352 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

Cottage in Round Hill

4.93 out of 5 average rating, 165 reviews

Best Countryside Retreat & No Cleaning Fees EVER

Luxurious & cozy cottage, nestled in Virginia's wine country. With a gas fireplace, amazing beds & linens, gourmet kitchen with EVERYTHING and the great hospitality of owners Jennifer and Eric, you will have a premier visit! Self check in anytime and we are on the 26 acre property for 24/7 service. Beautiful vistas, wineries, and activities, over 200 five-star reviews (Airbnb& VRBO) max privacy and convenience. Relax in our tranquil setting while enjoying all the delights of the region!

Guest favourite

Home in Bluemont

4.92 out of 5 average rating, 205 reviews

The Country French Cottage at High Meadows Estate

Come visit the alluring wine country of Bluemont Virginia, and stay in a beautifully appointed country French cottage on the 50 acre circa 1896 High Meadows Estate atop the Blueridge Mountains. Just 50 minutes west of Washington DC, this stunning country retreat is just 5 minute from the vineyards of Bluemont, the Shenandoah River, the Appalachian Trail, Hiking, Canoeing, Kayaking, Farmers Markets, the the cute villages or Berryville, Harpers Ferry, Luckettes, Middleburg and many more.

Guest favourite

Tiny home in Purcellville

4.98 out of 5 average rating, 130 reviews

King Bed-Tiny Home-Fire Pit-Historic Farm Stay

Escape to our newly renovated tiny cottage nestled in a charming 25-acre farm dating back to the 1700s! Enjoy a tranquil night in our one bedroom haven, boasting a king bed, speedy wifi, kitchen essentials, blackout shades, and a charming fire pit. Ideal for remote work retreats or romantic getaways! Explore nearby wineries, breweries, and scenic trails, and the quaint town of Purcellville, just 10 minutes away. Say hi to our friendly cows and pigs! Book now for an unforgettable stay!

Guest favourite

Guest suite in Round Hill

4.94 out of 5 average rating, 116 reviews

Sweet Suite on Snickersville!

Located near the town of Bluemont. The suite is located above a 3 car garage and is detached from the main house with about 450 sq ft. Has a queen bed & a loveseat sleeper sofa, a 3/4 bath, a breakfast nook with refrigerator, microwave & coffee maker. We are within 3 miles of Bear Chase Brewing, Dirt Farm, Bluemont Vineyard, Good Spirit Farm and more! Purcellville is a 15 minute drive has many amenities, major grocery stores, restaurants, golf courses and tennis courts.

Guest favourite

Cottage in Bluemont

4.95 out of 5 average rating, 172 reviews

The Cottage at Stonecroft

Circa 1902, the Cottage is nestled at the foot of the Blueridge Mountains. The location will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; living room, dining table and full kitchen on main level (note ceilings in living/dining room are 6'3"). Wifi, fire pit and small charcoal grill. Absolutely no pets/animals. The property has video security system on the exterior of the property only.

Guest favourite

Tiny home in Purcellville

4.97 out of 5 average rating, 315 reviews

Remote Tiny House in 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

Loft in Purcellville

4.99 out of 5 average rating, 294 reviews

"When Pigs Fly" Airbnb Most Hospitable Host in VA

Located between Middleburg, VA and Purcellville, VA, our loft is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. You will have views from every window in addition to all of the amenities you will need for a pleasant stay. We welcome your dogs while you visit. The only thing we ask is that you keep them off the couch, pick up their "business" and crate them if they are left alone.

Guest favourite

Flat in Bluemont

4.96 out of 5 average rating, 140 reviews

Charming private apartment

"Magical." This second story apartment, surrounded by giant spruces, is sited at the top of the Blue Ridge mountains, with a long sweep of lawn guiding the eye to the Shenandoah Valley below. The view is stunning. Peace and quiet reign. Here it's quiet except for the chirp of birds and an occasional "woof" from our Golden Retriever. Gardens are plentiful with flowers and the smell of old boxwood.