Upperville Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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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?

 

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Upperville Hotel Deals

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 CA $129 per night from Jul 26 to Jul 27
CA $129
CA $143 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,030 reviews)
"Everything was great except for the fact the shower was terrible. It felt like it took me an hour just to rinse the sham out of my hair because the water was coming out in a slow trickle. It was so bad I thought I would have to just rinse my head under the sink!"

Reviewed on Jul 10, 2026

TRU By Hilton 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 CA $288 per night from Aug 5 to Aug 6
CA $288
CA $386 total
Aug 5 - Aug 6
includes taxes & fees
8.8/10 Excellent! (1,009 reviews)
"My daughter and I stayed at Landdown resort for 2 nights. We used the pools and ate in 2 of the restaurants. Coton and Rye was hit and miss. Our first meal was great, but the second dinner was not. To be fair, tbe resrt did comp my meal and I was grateful. The pools were adequate, but could do with ..."

Reviewed on Jul 11, 2026

Lansdowne Resort and Spa
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 CA $98 per night from Jul 29 to Jul 30
CA $98
CA $111 total
Jul 29 - Jul 30
includes taxes & fees
9/10 Wonderful! (1,010 reviews)
"Great staff, clean rooms and delightful breakfast. I'll be back!"

Reviewed on Jul 5, 2026

Spark by Hilton Winchester
See all 752 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 Vacations
All Inclusive Vacations
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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 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?

  1. Choose your dates: The things you'd like to do in Upperville and your favourite season will help you decide when to get away.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

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