Upperville Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Aug 9 - Aug 10
Tomorrow
Aug 10 - Aug 11
Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24

Vacation Rentals in Upperville

Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Upperville Hotel Reviews

Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

10/10 Excellent
"I’ve stayed here before with my two dogs, this time without…..Rooms are very spacious and clean, Staff at desk always friendly and helpful. Breakfast good with friendly staff….Convenient off/on from Highway."
Laura 1-night trip
Posted 21 hours ago
Comfort Inn & Suites Winchester

Frequently asked questions

Can I find a vacation rental in Upperville?

Yes, we offer vacation rentals close to well known attractions in Upperville, or you can go with a more secluded option if you're looking for relaxation. Upperville is known for its restaurants.

How many vacation rentals are there in Upperville?

Choose from 4 Expedia vacation rentals in Upperville for a memorable vacation.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Blue Ridge Regional Park, or get outside and enjoy nature at Upperville Park. Sky Meadows State Park and Delaplane Cellars are a couple of places you'll find in the larger area.

What are vacation rentals like in Upperville?

Vacation rentals are private properties you can reserve for a few days or a quick weekend in Upperville. Vacation rentals offer extras such as WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of seclusion away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.