Skip to content
Sign up
Log in
Vacation rentals in Upperville

Vacation rentals in Upperville

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Upperville

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • "When Pigs Fly"  Wine Country!  Ale Trail!
    SUPERHOSTEntire loft · 2 guests · 1 bed · 1 bath
    "When Pigs Fly" Wine Country! Ale Trail!

    Located between Middleburg, VA and Purcellville, VA, our space is just about 15 minutes away from restaurants, wineries, breweries and many local points of interest. We offer an efficiency loft with views from every window. Although compact, we have provided all of the amenities you will need for a pleasant stay. We love our dogs and know you love yours too! We welcome your dogs while you visit. The only thing we ask is that you crate them if they are left alone.

    What guests are saying:

    “I stayed for 6 weeks at “When Pigs Fly” and loved it! Theresa and Rob were excellent hosts and went above and beyond to make sure I had everything I needed for my stay. The loft was clean, beautifully decorated, and included all the amenities needed for a long stay. I brought my dog with me, and she had plenty of space to walk around outside and around the loft. The location was beautiful, and the perfect place for a long stay or a quick trip.”

  • The Ark in Upperville
    Farm stay · 2 guests · 1 bed · 1 bath
    The Ark in Upperville

    Peaceful new apartment at the end of a beautiful country lane above a detached garage with panoramic views of grazing pastures, wildlife and animals. We have a small eclectic hobby farm with horses, donkeys, free ranging miniature ducks, peacocks and turkeys.We are 1/4 mile to the Upperville horse show grounds and 7 miles to the town of Middleburg. Our farm is the perfect place for animal lovers to have a quiet getaway conveniently located to many great restaurants and wineries.

    What guests are saying:

    “The location is peaceful and beautiful! The apartment is clean, new, and has everything you could need. The hosts are friendly, welcoming, and very accommodating. You can interact with all the adorable farm animals, which are very friendly as well. You can go for long walks, sit by the fire, and unwind from all the world's stresses while here. I will definitely be back!”

  • Noctiluca Farm & Wine Trail Getaway
    SUPERHOSTEntire apartment · 5 guests · 2 beds · 1 bath
    Noctiluca Farm & Wine Trail Getaway

    Charming wine country getaway in Purcellville, just minutes from the Loudoun Wine Trail, antique shops, breweries & more! Beautiful private apartment on a 5-acre farm. Come out to the country for a weekend or holiday and enjoy the use of a Virginia Wine Pass, which will give discounts and free wine tastings at participating wineries. Minutes from the WO&D trail, & you can store your bikes in the spacious garage. Ask us about transportation to weddings & wineries! Se Habla Español!

    What guests are saying:

    “Megan & Pablo were great hosts! Firstly, their property is amazing - Clean, well kept and 2 beautiful + friendly dogs. We had a very comfortable stay at their place. It is spacious, stocked up with all the amenities you need and was very clean. It is also very conveniently located - Close to many vineyards, breweries and restaurants but still has the vibe of a quite country house! I will definitely recommend their spot to anyone who is looking to have a relaxing weekend in VA! We hope to be back soon ourselves too :)”

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Upperville vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Upperville

Ashby's Perch -- A Very Special Retreat
SUPERHOSTEntire house
Ashby's Perch -- A Very Special Retreat
Price:R4,633 ZAR / night
Comfy Blue Ridge Mountains Log Cabin (Ravenswood)
SUPERHOSTPrivate room
Comfy Blue Ridge Mountains Log Cabin (Ravenswood)
Price:R842 ZAR / night
A Castle in the Woods at Bluemont VIrginia
Private room
A Castle in the Woods at Bluemont VIrginia
Price:R1,011 ZAR / night
Charming bed/bath w/views & space to telecommute
SUPERHOSTPrivate room
Charming bed/bath w/views & space to telecommute
Price:R708 ZAR / night
Large Modern House, Wine Country
SUPERHOSTEntire house
Large Modern House, Wine Country
Price:R4,212 ZAR / night
Beau Ridge Cabin.
SUPERHOSTEntire cabin
Beau Ridge Cabin.
Price:R1,988 ZAR / night
Private Mountain Room
SUPERHOSTPrivate room
Private Mountain Room
Price:R421 ZAR / night
Studio - Long Term Rental
Entire apartment
Studio - Long Term Rental
Price:R758 ZAR / night
The Blue Door Cottage in Wine Country
SUPERHOSTEntire cottage
The Blue Door Cottage in Wine Country
Price:R1,617 ZAR / night
The Country French Cottage at High Meadows Estate
SUPERHOSTEntire house
The Country French Cottage at High Meadows Estate
Price:R2,611 ZAR / night
Carson Mountain Cottage
SUPERHOSTEntire cottage
Carson Mountain Cottage
Price:R1,904 ZAR / night
Private walkout basement with patio by the pond
SUPERHOSTPrivate room
Private walkout basement with patio by the pond
Price:R1,095 ZAR / night
Show all