Holiday houses in Round Hill

4.87 out of 5 average rating, 229 reviews

Home in Bluemont

The Old Schoolhouse at High Meadows Estate

The Old Schoolhouse at High Meadows is a beautifully appointed historic cottage set amidst a tranquil 50 acre estate of gardens and old barns. Close to wineries, breweries, the Appalachian and W&OD Trails and many historic villages (Middleburg, Upperville, Harpers Ferry) and only minutes from the Shenandoah River, this superbly decorated cottage is a wonderful get away from Washington DC and perfect for a couple or small family. Activities abound, or just visit local farmers’ markets and read.

Tiny home in Harpers Ferry

4.98 out of 5 average rating, 123 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.

4.99 out of 5 average rating, 542 reviews

Cabin in Bluemont

Rustic Blue Ridge Cabin

A quaint rustic cabin nested at the top of the Blue Ridge Mountains, with a detached 150 ft² bedroom, 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- 4person 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!This is a rustic not luxurious cabin!

4.99 out of 5 average rating, 110 reviews

Welcome to the Hidden Hive!

The Hidden Hive is located on beautiful, tranquil farmland, within a few minutes of Loudoun County’s premiere wineries and breweries. Rest your head here after a hard day’s hike on the Appalachian Trail or a celebratory evening at a Bluemont wedding. We are a hobby farm and own chickens, goats, dogs, and barn kitties. Wildlife such as deer can be seen, and owls heard here at night. You may see cyclists or horseback riders pass along our historic Civil War roads. We can’t wait to host you!

Guesthouse in Purcellville

4.98 out of 5 average rating, 241 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.

Cottage in Round Hill Village

4.93 out of 5 average rating, 189 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!

Farm stay in Round Hill Village

4.93 out of 5 average rating, 412 reviews

The Goat Loft - A Private, Peaceful Getaway!

Private Blue Ridge Retreat – Nature, Hiking, and Relaxation Escape to 13 acres of peaceful woodlands and pasture at the base of the Blue Ridge Mountains. Enjoy the goats from the private deck, perfect for stargazing at night! Nearby, hiking on the Appalachian Trail, cycle scenic routes, or explore historic towns, wineries, and breweries. The Potomac and Shenandoah Rivers offer even more outdoor adventures. A perfect mix of tranquility and adventure, but just minutes from everything!

4.99 out of 5 average rating, 311 reviews

Home in Purcellville

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.

4.96 out of 5 average rating, 213 reviews

Cottage in Bluemont

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.

Farm stay in Purcellville

4.99 out of 5 average rating, 362 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.

4.86 out of 5 average rating, 162 reviews

24 Acre Lamontagne Farm House

Located at the base of the Blue Ridge Mountains in Bluemont, VA only 20 minutes from Leesburg, 5 minutes from Bluemont Vineyards, Dirt Farm Brewing, 10 minutes to B Chord Brewing and Bear Chase, and Henway Cider. This perfect historic house has so much charm and character to offer it makes the perfect getaway for visiting Loudoun County. The other bedrooms are left vacant on purpose and not for occupancy. Please reach out for recommendations : )

Guesthouse in Round Hill Village

4.97 out of 5 average rating, 454 reviews

Private Carriage House

A recently renovated carriage house by an interior designer situated on a treed and private property conveniently located for exploring wineries, breweries, horse events or civil war sites in Middleburg, Purcellville, Leesburg, Bluemont or Round HIill. Enjoy the sounds and sights of nature and fresh air. Recharge in a peaceful setting. Adults only. No pets, children or infants.

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Other great holiday rentals in Round Hill

Apartment in Purcellville

5 out of 5 average rating, 48 reviews

Lovely One bedroom apartment with pool

JillRating, 5 stars1 week ago

I thought the place was perfect! Judy stocked the mini-fridge with awesome breakfast items to include bagels and cream cheese! From sitting outside to relaxing inside was just a great time. Their pup was the best! She would greet me every morning while having coffee…sweet girl! Would I stay there again…absolutely! Judy is an awesome host!

4.99 out of 5 average rating, 96 reviews

Guesthouse in Bluemont

Bluemont Escape:Walk to Bears Den; Bear Chase Brew

LilyRating, 5 stars3 weeks ago

We absolutely loved our stay here! It was super clean and very spacious! Amanda was a very accommodating host and I would definitely recommend this place!

Apartment in Purcellville

4.95 out of 5 average rating, 57 reviews

#2 Cottage in Loudoun Co. (Upper of 2 units)w/Pond

JohnnaRating, 5 stars4 days ago

We love staying here when we visit our daughter and her family in Purcellville. Greg’s accommodations are lovely, peaceful, beautiful and wonderfully appointed. We didn’t see Nemo this visit, but we were in and out at odd hours so maybe we missed his gentle smile. We can’t wait to return.

Guesthouse in Round Hill Village

4.78 out of 5 average rating, 451 reviews

Private detached garage suite

RitaRating, 5 stars1 month ago

Had a great stay. Would recommend to others.

4.94 out of 5 average rating, 85 reviews

Private apt with views on a beautiful horse farm

ElisabethRating, 5 stars1 week ago

I am a repeat guest and absolutely will be again in the future. Love the space, and the gorgeous farm and location. Hosts are so friendly and helpful. The farm flowers are always such a nice touch and the covered porch is convenient. Bed is comfortable and the internet is great! Everything you need :)

Guesthouse in Purcellville

4.88 out of 5 average rating, 56 reviews

Garden Cottage

SteveRating, 5 stars1 month ago

Brenda’s place was great. It was perfect for our getaway weekend and extremely convenient to the reunion which we attended. It’s close to many wineries and nice restaurants in the surrounding communities.

4.93 out of 5 average rating, 45 reviews

Home in Bluemont

It's Own Destination/Farm Cottage with Mtn. Views

DebbieRating, 5 stars2 weeks ago

The home was extremely comfortable & peaceful since it is out in the country. The house offers spacious common areas for interacting & dining. Beds & linens were quality & comfortable. Kitchen was well equipped which was helpful since restaurants were in town.