Upperville Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Upperville Vacation
When you choose a Upperville vacation package, you can relax and enjoy your getaway to the fullest. Uncover the sights and sounds of this fascinating city knowing that everything has been taken care of in advance. During your trip to Upperville, take all the time you need for sightseeing. A fantastic place to begin is Sky Meadows State Park. Expedia is here to help you escape the everyday. Tailor your vacation to Upperville to match your travel style, whatever that may be.
Ready to book your vacation to Upperville?
Upperville Hotel Deals
Lansdowne Resort and Spa
44050 Woodridge Pkwy Leesburg VA
Fully refundableReserve now, pay when you stay
CA $274
CA $370 total
Sep 13 - Sep 14
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"All great . The front staff woman this morning was a little rude but overall it was a great stay"
Reviewed on Aug 30, 2026
Salamander Resort And Spa
500 North Pendleton Street Middleburg VA
CA $956
CA $1,167 total
Sep 1 - Sep 2
includes taxes & fees
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
CA $107
CA $122 total
Sep 28 - Sep 29
includes taxes & fees
9.2/10 Wonderful! (1,007 reviews)
"Everything was very nice and clean, much appreciated"
Reviewed on Aug 31, 2026
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.
Frequently asked questions
How much does an Upperville vacation package cost?
You'll find cheap prices on Expedia for your Upperville break. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Upperville costs.
What are the cheapest months to go to Upperville?
The off-season is the best time to travel to Upperville if you're on a budget. Another tip for getting cheap Upperville vacation packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Upperville?
With a well-planned itinerary, you can easily hit the most popular Upperville sights in a few days. But if you want to explore off the beaten track or take day trips, consider booking your Upperville vacation for longer.
How to find the best Upperville package deals?
Landing a cheap Upperville package deal is a breeze with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and see what's available. You can personalize your search by "Amenities," "Property type," "Guest rating" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Upperville package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Upperville vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still get the freedom to create a personalized Upperville vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Upperville?
If you're considering a spontaneous Upperville trip, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land sensational deals on your hotels and flights by booking ahead.
How to plan a trip to Upperville?
- Choose your dates: The things you'd like to do in Upperville and your favourite season will help you decide when to get away.
- Budget wisely: In addition to the price of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Upperville.
- Work out your trip length: Think about how long you'd like to spend exploring Upperville. Plan your itinerary so you can get to all the attractions and activities you're interested in at a leisurely pace.
- Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find an Upperville vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
