Holiday houses 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, 446 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!

9 – 16 Nov

$2,140 AUD total

Guest favourite

Farm stay in Round Hill

4.98 out of 5 average rating, 234 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.

26 Oct – 2 Nov

$2,962 AUD total

Guest favourite

Cottage in Bluemont

4.95 out of 5 average rating, 171 reviews

The Cottage at Stonecroft

Nestled at the foot of the Blue Ridge Mountains among beautiful rolling hills, on a working horse farm outside the village of Bluemont. This circa 1902 Cottage will put you in touch with the history of the area, antique shops, wineries/breweries and nearby hiking. 2 bedrooms and bath upstairs; sitting/living room , dining table and full kitchen on main level. Wifi, fire pit and small charcoal grill. Over 21 only. Absolutely no pets/animals. For your safety property has video security system.

12 – 19 Mar

$1,765 AUD total

Guest favourite

Farm stay in Round Hill

4.94 out of 5 average rating, 347 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.

17 – 24 Aug

$1,627 AUD total

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!

29 Oct – 5 Nov

$3,727 AUD total

Guest favourite

Home in Bluemont

4.93 out of 5 average rating, 203 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.

22 – 29 Aug

$1,967 AUD total

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!

27 July – 3 Aug

$2,447 AUD total

Guest favourite

Tiny home in Purcellville

4.96 out of 5 average rating, 313 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!

4 – 11 Oct

$2,020 AUD total

Guest favourite

Farm stay in Purcellville

4.99 out of 5 average rating, 316 reviews

Cozy Cuddle up on 1700’s Clydesdale Farm

The Hunt Box at Sylvanside Farm is a couples favorite! Cozy bedroom with bay window overlooks the stone barn, Clydesdales field and pond. Full kitchen, full bath and small living room. Enjoy a glass of wine on dock, hike the fields and streams, enjoy the animals, roam the our beautiful 25 acres. Escape the city and relax. Our visitors to date have proclaimed it magical and we hope you agree. In accordance with Airbnb’s policies parties are not permitted.

$293 AUD per night

Guest favourite

Loft in Purcellville

4.99 out of 5 average rating, 289 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.

8 – 15 Sept

$1,412 AUD total

Guest favourite

Apartment 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.

7 – 14 Oct

$1,728 AUD total

Guest favourite

Home in Purcellville

4.93 out of 5 average rating, 122 reviews

Historic Tip of the Hill, Purcellville, Virginia

Historic Tip of the Hill, ca 1762, is located just a 1/2 mile outside of the town of Purcellville, VA. Close to all the major wedding venues. Restaurants, wine tasting, breweries, live music, the AT, Shenandoah River, W,O&D bike trail & more are just minutes away. This 18th century home has been completely updated but with its charm and character intact. 3 BR, 1.5 BA, sleeps up to 6.

11 – 18 Nov

$5,158 AUD total