Upperville Holidays

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Upperville Holiday

Our pick of the best Upperville Hotel Deals

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 NZ$474 per night from 29 July to 30 July
NZ$474
29 July - 30 July
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"Great room, lovely amenities"

Reviewed on 8 July 2026

Lansdowne Resort and Spa
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$176 per night from 26 July to 27 July
NZ$176
26 July - 27 July
includes taxes & fees
9.2/10 Wonderful! (1,025 reviews)
"Surprised by the affordable Hilton hotel. Room was nice & quiet. We will look for this brand in our future travels."

Reviewed on 10 July 2026

TRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is NZ$139 per night from 30 July to 31 July
NZ$139
30 July - 31 July
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on 5 July 2026

Spark by Hilton Winchester
See all 754 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.

Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
See properties

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.

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