Vacation rentals in Upperville

4.95 out of 5 average rating, 301 reviews

Apartment in Bluemont

A Great Getaway — Foxglove Retreat

Nestled in the Blue Ridge Mountains, "Foxglove Retreat" offers you complete privacy and beautiful vista views of the Shenandoah Valley. Equipped with all the necessities for a relaxed and luxurious experience, the "Foxglove Retreat" is sure to become one of your favorite destinations. "Foxglove Retreat" is ideally located near popular tourist destinations, restaurants and wineries. The Bears Den Trail Center is walking distance for those who would like to explore the beauty of the Blue Ridge Mountains on foot. For those who seek nearby shopping and sightseeing, the quaint village of Middleburg is to the southeast and has many antique shops and elegant boutiques nestled in its historic buildings. To the east is the town of Leesburg featuring the upscale Leesburg Corner Premium Outlets and the Leesburg Farmers’ Market. To the west is the Old Town of Winchester where you will discover charming shops, restaurants, galleries, centuries-old architecture, and historical landmarks.

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.

4.94 out of 5 average rating, 128 reviews

Cottage in Middleburg

English Cottage

MIDDLEBURG ADDRESS. Three night min during Sept. horse show. Best country/Middleburg location. Five (+/-) min to town, restaurants, shopping, wedding venues. Centrally located to vineyards, breweries, horse events, more.. Guests 'LOVE' this CLEAN, tasteful, charming/Old English style - private cottage.' Bdrm w/2 twin or together as king bed. (Can separate beds if requested.) Bath w/ rain shower. Kitchenette appointed with modern appliances. Stainless refrig., micro, toaster oven & Keurig.

4.99 out of 5 average rating, 108 reviews

Farm stay in Bluemont

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!

4.99 out of 5 average rating, 113 reviews

Cabin in Front Royal

Beautiful mountain cabin, lake, recreational areas

Blue Mountain Cabin is situated at 1,700 feet. Fish, swim, walk to nearby private Deer Lake. Located in Front Royal on Blue Mountain near Skyline Drive, Skyline Caverns, Wildlife Management Area, Appalachian Trail, G.W. National Forest, Fox Meadow Winery. Horseback riding nearby. Near the town of Front Royal, city of Winchester and outdoor movie theatre in Stephens City. Element on Main Street, Spelunker's and Melting Pot Pizza, local favorites. We offer wi-fi, landline phone, TV, views!

Farm stay in Round Hill Village

4.93 out of 5 average rating, 411 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!

4.91 out of 5 average rating, 106 reviews

Cottage in Paris

Quaint cottage in historical town of Paris VA!

Welcome to my home! This house was built in the 1820’s in the historical town of Paris, Virginia! With lots of history and character this house still has some of the original exposed beams and hardwood flooring! If you enjoy the outdoors, wineries, breweries, and shopping this is a perfect location for your stay! Minutes from the Appalachian trail, and Sky Meadows park there’s plenty of hiking around. Famous Ashby Inn restaurant just a short walk away and many more amazing places!

4.91 out of 5 average rating, 130 reviews

Farm stay in Middleburg

Self-contained apartment on Organic vegetable farm

Enjoy a relaxing retreat at a genuine sustainable organic vegetable farm. This self-contained apartment is the perfect location for a family get away, or overnight stay whilst visiting the many local wineries and breweries. The farm is located just 5 miles from historic Middleburg, right in the middle of hunt country. See what life is like on a working farm, with seasonal healthy vegetables growing just steps from the door and farm animals grazing outside your window.

4.91 out of 5 average rating, 182 reviews

Home in Upperville

Upperville Hunt Country Cottage

The home has a standing seam metal roof, clapboard-style siding, a stone foundation, a cozy front porch, and second-floor dormer windows. The interior is painted with warm colors and accented by antique oak barn wood paneling and trim in the family room. The flooring is the original antique heart pine. The cottage is decorated as a traditional English Hunt Box, with equine art and memorabilia, lovely antiques, warm carpets on the heart pine floors, and high-end bed linens.

4.95 out of 5 average rating, 211 reviews

Cabin in Front Royal

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

4.96 out of 5 average rating, 211 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.

4.94 out of 5 average rating, 154 reviews

Cabin in Upperville

Island cabin

Getaway from the city and escape to the countryside in this beautiful cabin recently renovated. Situated on a beautiful private lake, enjoy your morning coffee on the porch over looking the water, or enjoy the fire pit with the sunset. The cabin features a queen size bed, a full bathroom, a kitchenette, and a cozy living room area. There is also an outside grill and fire pit. We recently updated the kitchen and added a full size fridge/freezer.

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Other great vacation rentals in Upperville

4.89 out of 5 average rating, 119 reviews

Cabin in Linden

Skyland Hideaway | Mountain Cabin w/ Hot Tub

DianeRating, 5 stars1 month ago

My friend and I had an amazing stay at Matt’s cabin in Linden! Needed to get away from the hustle and bustle of Northern Virginia . The cabin had everything you could possibly want. We enjoyed the fire pit every night. My friend enjoyed the hot tub every morning , it was nice and clean. Not far of a drive into the local town of Front Royal. Went for a beautiful walk around the Shenandoah river. We would definitely stay here again.

Cabin in Augusta ( Capon Bridge)

4.96 out of 5 average rating, 152 reviews

Nirvana, Mountain View

TylerRating, 5 stars1 month ago

Staying at Su’s Airbnb was an absolute delight—the location is exactly as photographed, and even more beautiful in person, with serene surroundings that made it the perfect escape for peace and quiet. Su went above and beyond to make me feel welcome, adding thoughtful touches that truly made the stay special. Every detail of the space reflects care and warmth, and I felt instantly at ease from the moment I arrived. It’s rare to find a place that feels both stunning and soul-soothing, and I will very likely be returning one day.

4.88 out of 5 average rating, 130 reviews

Home in Cross Junction

The Little Red Schoolhouse

CindyRating, 5 stars1 week ago

My husband and I spent our first night away after our kiddo was born and it was wonderful! Being able to relax with no agenda (or nap schedules) in such a beautiful place was amazing. The school house was so nice and we loved all of the little school house decor throughout the place. Everything was clean and pristine! The hot tub was a wonderful way to unwind! We spent less than 24 hours here but it was worth it. Hope to be back again! Thank you for letting us stay!

4.99 out of 5 average rating, 67 reviews

Cottage in Harpers Ferry

Cozy Mountain Cottage Perfect for Friends & Family

MichaelaRating, 5 stars3 weeks ago

Had a very nice stay here. Beautiful area. House was very clean. I loved that there was a big Tv in every bedroom. We ended up staying in the basement bedroom over the master bedroom because no light gets in - LOVE that. Also really enjoyed the ping pong and foosball tables. Would definitely stay again if ever in the area!

4.83 out of 5 average rating, 251 reviews

Home in Harpers Ferry

Larger Families, Hot tub, Campfire Ring, Rural

A.J.Rating, 5 stars3 weeks ago

We had a lovely stay at Laura's 'Adventure Inn.' House is older but has been renovated well. It's quite cozy! Highly recommend if looking for a place in Harper's Ferry area.

4.81 out of 5 average rating, 438 reviews

Cabin in Harpers Ferry

Cozy Cabin Hidden Away on a Lake!

JohnRating, 5 stars2 weeks ago

Excellent stay! Beautiful locale! Would stay again for sure!

4.9 out of 5 average rating, 189 reviews

Cabin in Luray

1850's Massanutten Spgs -"Charmed by the Ambiance"

MarandaRating, 5 stars1 month ago

We absolutely loved our stay! The place was easy to find and access. It is conveniently located in Luray close to the town and attractions, but also far enough away to unplug and have privacy. We really enjoyed the hot tub and fire pit while star gazing. Would highly recommend and would book again!