Upperville Vacation Packages

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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.

Top Upperville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Save 100% on your flight
per person
Sep 4 - Sep 8
found 2 days ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,009 reviews)
Very clean and quiet. The staff was very friendly

Reviewed on Jul. 14, 2025

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.2/10 Very Good! (1,001 reviews)
Very quiet and clean.

Reviewed on Jul. 9, 2025

Hotel Burg

Hotel Burg

4 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
No reviews
Washington Hilton

Washington Hilton

4 out of 5
Northwest
per person
Sep 4 - Sep 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8/10 Very Good! (1,011 reviews)
Great hotel with a great location. Only a 45 minute walk from the national mall, with a ton of good food options on the way

Reviewed on Jul. 12, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
Sep 4 - Sep 8
found 2 days ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,488 reviews)
Teddy was the best! He's the reason we enjoyed our stay! The other staff members were unfriendly, disinterested and unhelpful. Not just these staff members though, but generally other places too. But I cannot say enough wonderful things about Teddy the doorman-valet! He should be promoted to concierge! Bad shower pressure. No ice machine. Had to ask for a full length mirror. Rooms are New York small, and unnecessary furniture in the room taking up too much space. More hooks needed in the bathroom for towels, I was with my husband and we had a king, so it would make more sense that the bathroom would need more towel racks. But my biggest complaint is that they put a Nespresso machine in the room instead of a Keurig. The front desk kept giving me decaf, and didn't know the difference between the pods, and argued with me about it until I showed her the pods online. Then she just said she'd send housekeeping but didn't. I had to go buy my own. Keurig is easier to use, easier to find in a store, and make a real size cup of coffee. Just an irritant. Please hired friendly helpful people to work at the Lyle. I'm in the service industry for 40 years, and still working so I know how to treat customers!

Reviewed on Jul. 14, 2025

Ready to book your vacation to Upperville?

 

Choose your dates

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 CA $301 per night from Jul 20 to Jul 21
CA $301
CA $394 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"The rooms we’re comfortable, friendly staff and great location."

Reviewed on Jul. 14, 2025

Lansdowne Resort and Spa
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 CA $159 per night from Jul 20 to Jul 21
CA $159
CA $173 total
Jul 20 - Jul 21
includes taxes & fees
9/10 Wonderful! (2,078 reviews)
"Our only complaint was the noise as the hotel is at a busy intersecrion."

Reviewed on Jul. 15, 2025

La Quinta Inn & Suites by Wyndham Winchester
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 CA $94 per night from Jul 20 to Jul 21
CA $94
CA $103 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,105 reviews)
"The value of this property was great. For the price paid we feel we received a very good room to sleep in for one night on a road trip. Breakfast was better than others in this price range. We drove 1.5 miles to Old Town Winchester for dinner and it was interesting and fun to walk through. The only ..."

Reviewed on Jul. 16, 2025

Travelodge by Wyndham Winchester
See all 705 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

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Upperville vacation package cost?
You'll find cheap prices from CA $567 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.

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