Photo by Michael Gibson

Upperville Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
1 Jan - 2 Jan
Tomorrow
2 Jan - 3 Jan
This weekend
2 Jan - 4 Jan
Next weekend
9 Jan - 11 Jan

Our top choices for Upperville holiday rentals

Interior
'thomson Farm' Classic Home < 10 Mi to Vineyards!

Cottage in Leesburg

'thomson Farm' Classic Home < 10 Mi to Vineyards!
3.0 star property
The price is HK$8,450
HK$14,218 total
includes taxes & fees
2 Jan - 3 Jan
'thomson Farm' Classic Home < 10 Mi to Vineyards!
Interior
Balcony & Pool Access: Modern Gainesville Home

Apartment in Gainesville

Balcony & Pool Access: Modern Gainesville Home
3.5 star property
The price is HK$1,229
HK$3,870 total
includes taxes & fees
2 Jan - 3 Jan
Balcony & Pool Access: Modern Gainesville Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
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

Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

10/10 Excellent
"Yes"
Kelly 1-night trip
Posted 2 days ago
Microtel Inn & Suites by Wyndham Winchester

Find out more about Upperville

Search for holiday rentals in Upperville on Expedia! You can easily find your home rentals, villas, holiday apartments in Upperville using one of the methods below:

  • View our selection of featured holiday rentals in Upperville
  • Use the map to find apartments and other holiday homes in the Upperville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Upperville while they last

Look no further and take a look at our great range of rental properties in Upperville!

Frequently asked questions

Can I find a holiday rental in Upperville?

Yes, there are holiday rentals close to the most popular sights in Upperville, or you can select a more secluded option if you're looking for a relaxing stay. Upperville is known for its restaurants.

What are some of the best holiday rentals that Upperville has to offer?

Charming 3-bedroom house with firepit and game room in gorgeous Harpers Ferry: This holiday home rental outside of Upperville is located in the mountains, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Upperville?

Choose from 5 Expedia holiday rentals in Upperville for a memorable holiday.

What can I see and do in Upperville?

While exploring the area, visit family-friendly sights like Dinosaur Land, 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 wider area.

What are holiday rentals like in Upperville?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Upperville. Holiday rentals feature extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for families.