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.
Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (2,464 reviews)
Clean, excellent quality, friendly stuff. Restaurant is of an excellent quality, although maybe a little more expensive that I would expect. Good location for the purpose of my visit. Relatively far from the subway stations though; however buses are coming near.

Reviewed on Jun. 19, 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Sep 9 - Sep 12
found 9 hours ago
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
10/10 Exceptional! (2 reviews)
My husband and I stayed here for our anniversary and it did not disappoint. We will definitely be coming back. The staff, the hotel, the restaurants- all absolutely amazing.

Reviewed on Jun. 22, 2025

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
Save 100% on your flight
per person
Aug 1 - Aug 4
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,000 reviews)
Want to go back soon

Reviewed on Jun. 25, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Staff were very friendly at check in and even went above and beyond (unasked) to see if a room upgrade was available. The room was clean, well appointed and very comfortable.

Reviewed on Jun. 25, 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on Jun. 24, 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 $267 per night from Jun 30 to Jul 1
CA $267
CA $356 total
Jun 30 - Jul 1
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"We had a great stay and excellent bday connect Coton & Rye. Pete the manager and Morgan the waitress went above and beyond to accommodate our large family with 5 children including 3 two year olds. They were very kind, helpful, and flexible."

Reviewed on Jun. 21, 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 $142 per night from Jul 6 to Jul 7
CA $142
CA $155 total
Jul 6 - Jul 7
includes taxes & fees
9/10 Wonderful! (2,066 reviews)
"Stay was okay, clean hotel, but minor inconveniences will cause me not to stay here again. A nice pet friendly hotel, but don't care for dogs in the tiny breakfast serving room. Also, the hotel will not transfer an outside call to a room or allow direct room calling."

Reviewed on Jun. 24, 2025

La Quinta Inn & Suites by Wyndham Winchester
Hilton Garden Inn Dulles North
Hilton Garden Inn Dulles North
3 out of 5
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
The price is CA $143 per night from Jul 5 to Jul 6
CA $143
CA $163 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"This is an excellent Hotel the breakfast is very good and the service and I'm very nice pool and hot tub and best of all free parking"

Reviewed on Jun. 22, 2025

Hilton Garden Inn Dulles North
See all 710 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 $556 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.