Upperville Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Michael Gibson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$173 per night from 1 Sept to 2 Sept
AU$173
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,127 reviews)
"Loved this hotel Clean, friendlt staff, great breakfast and dog friendly"

Reviewed on 14 Aug. 2025

La Quinta Inn & Suites by Wyndham Winchester
Lansdowne Resort and Spa

Lansdowne Resort and Spa

4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
The price is AU$458 per night from 1 Sept to 2 Sept
AU$458
1 Sept - 2 Sept
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Excellent couples getaway for Fourth of July, including great fireworks display. The pools and spa/fitness amenities are top notch and charming historic Leesburg is a 10-minute drive from the property."

Reviewed on 11 Aug. 2025

Lansdowne Resort and Spa
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is AU$142 per night from 31 Aug to 1 Sept
AU$142
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,002 reviews)
"Bed comfort"

Reviewed on 12 Aug. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 700 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.