Upperville Vacation Rentals
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Our top choices for Upperville vacation rentals
1. Lunar Loft, with mountain views
Lunar Loft, with mountain views
2. 18th Century Stone Cottage minutes from historic Middleburg
18th Century Stone Cottage minutes from historic Middleburg
3. Blue Mountain Cabin, secluded, perfect for couples, near main road
Blue Mountain Cabin, secluded, perfect for couples, near main road
4. Peaceful mountain cabin in charming Berryville VA - next to river and brewery
Peaceful mountain cabin in charming Berryville VA - next to river and brewery
5. "The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
"The Love Nest" - Stunning Views overlooking the Shenandoah in Wine Country
6. Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
Chipmunk Hollow | Hot Tub, Grill & Fire Table | 3BR, Sleeps 6
7. Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
Stylish 1-bd/1-ba gardern apt within quaint Bluemont village, walk to wineries.
8. The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
The Honeymoon Cabin | Private Couple's Retreat w/ hot tub
Find vacation rentals that suit your style
Top Upperville Hotel Reviews
Comfort Inn & Suites Winchester
Find out more about Upperville
Everything you need to know about Upperville vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Upperville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Upperville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Upperville vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Upperville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Upperville in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $221 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Upperville rentals
At Expedia, we put the best Upperville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Upperville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Upperville vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Upperville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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