Vacation Summer Rental - Vacation Rentals in Upperville
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Luxury Places to Stay in Upperville
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Top-Rated Vacation Rentals with a Pool in Upperville
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Pet-Friendly Vacation Rentals in Upperville
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Large Vacation Homes & Villas in Upperville
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Upperville Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Upperville
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About Upperville Vacation Rentals
With more than 55 Upperville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Vacationsummerrental and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Upperville.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Vacationsummerrental Upperville, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Upperville. Places to stay near Upperville are 1272.65 ft² on average, with prices averaging US $669 a night.
Vacationsummerrental makes it easy and safe to find and compare vacation rentals in Upperville with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Top Rental Accommodation Types in Upperville
| Type | Count |
|---|---|
| Vacation Homes | 34 |
| Cottages | 9 |
| Cabin Rentals | 6 |
| Villas | 2 |
| Holiday Apartments | 1 |
| Hotels | 1 |
| Others | 1 |
| Ski Chalet Rentals | 1 |
Use these Quick Filters to Find a Vacation Rental in Upperville
★ Pro Tip: Vacationsummerrental makes it easy to compare the best listings on Vacationsummerrental homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Vacationsummerrental homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Upperville.
Weather in Upperville
View the weather forecast for Upperville before booking your Upperville Vacation Rentals to confirm your best time to go.
Upperville Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Upperville?
There are a lot of options in Upperville. If you plan on staying in the Upperville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Upperville:
- Stylishly restored 1800's historic home- heart of Virginia hunt & wine country!
- 18th Century Stone Cottage minutes from historic Middleburg
- Lovely Guest House 2.5 miles from downtown Middleburg
- Hunt Country cottage in Upperville!
- Historic house in Upperville! Wineries, equestrian events, great location!
- Cozy Country Getaway in the Heart of Upperville
- Peaceful Mountain Retreat Near Appalachian Trail, Wineries, Breweries and More
- Renovated 1880s farmhouse near the Blue Ridge and Sky Meadows with amazing views
- Charming 3-bedroom cottage located on historic Seaton Place Farm in Delaplane VA
- Historic home nestled in the heart of horse and wine country. Kids/pet friendly!
Which vacation homes in Upperville are best for families?
If you are looking for a family-friendly vacation home in Upperville, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Upperville:
How many vacation rentals are available in Upperville?
Currently, the total number of properties listed in 2026 is over 55 in the Upperville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Upperville.
