Upperville Holidays

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Your Upperville Holiday

Cuisine, art, entertainment and more … It's all waiting for you with an Upperville holiday package. And with the ability to customise your city break, it's guaranteed to be one to remember. Sky Meadows State Park is among the big-ticket attractions to add to your itinerary during a trip to Upperville. Expedia will help you escape your daily routine. Tailor your holiday to Upperville to match your travel style, whatever that may look like.

Upperville Holiday

Upperville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Barrel Oak Winery, The Boxwood Winery and Philip Carter Winery

Our pick of the best Upperville Hotel Deals

Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$114 per night from 10 July to 11 July
AU$114
10 July - 11 July
includes taxes & fees
8.4/10 Very Good! (1,115 reviews)
"I liked we could walk to IHOP or Cracker-barrel for a meal."

Reviewed on 2 Jul. 2025

Travelodge by Wyndham Winchester
Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is AU$450 per night from 16 July to 17 July
AU$450
16 July - 17 July
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Outstanding place for a mini-vacation whether it's you and your love, you and your friends or even you and your kids!"

Reviewed on 30 Jun. 2025

Lansdowne Resort and Spa
Hilton Garden Inn Dulles North
Hilton Garden Inn Dulles North
3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
The price is AU$197 per night from 13 July to 14 July
AU$197
13 July - 14 July
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"evything fine"

Reviewed on 27 Jun. 2025

Hilton Garden Inn Dulles North
See all 710 properties in Upperville
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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does an Upperville holiday package cost?
You can snap up a holiday package to this popular destination on Expedia. But how much your holiday to Upperville costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Upperville?
Plan your getaway for the off-season and you're likely to score cheap Upperville holiday packages. Keep in mind that school holiday periods and local festivals and events can have an impact on prices, so do your research before booking.
How many days is enough for Upperville?
Typically, a handful of days is enough to see the major attractions during your Upperville holiday. However, if you want to have time to rest or take day trips, consider extending your itinerary.
How to find the best Upperville package deals?
Begin your search for an Upperville package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the ideal Upperville package deal right away, simply change your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Upperville escape off to a flying start.
Is it cheaper to book an Upperville holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a personalised Upperville holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Upperville?
If you're considering a spur-of-the-moment Upperville trip, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
How to plan a trip to Upperville?

  1. Pick the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Upperville.
  2. Budget wisely: On top of the price of your accommodation, you'll need to consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Upperville.
  3. Decide your trip length: Consider how much time you want to spend discovering Upperville. Plan your days so you can get to all the experiences and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Upperville holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.