Upperville Holidays

Photo by Michael Gibson

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Top Flight + Hotel Deals in Upperville

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Washington DC Dupont Circle

The Royal Sonesta Washington DC Dupont Circle

4.5 out of 5
Northwest
per person
31 Jul - 7 Aug
found 1 day ago
Return flight included
Lisbon (LIS) to Washington (DCA)
8.6/10 Excellent! (1,178 reviews)
Good room. Not microwave available.

Reviewed on 24 Jun 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
31 Jul - 7 Aug
found 1 day ago
Return flight included
Lisbon (LIS) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
The property was beautiful and centrally located to attractions.

Reviewed on 24 Jun 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
31 Jul - 7 Aug
found 1 day ago
Return flight included
Lisbon (LIS) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
Clean and convenient

Reviewed on 24 Jun 2025

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
per person
31 Jul - 7 Aug
found 1 day ago
Return flight included
Lisbon (LIS) to Washington (DCA)
9.4/10 Exceptional! (1,001 reviews)
Never a disappointment. Staff are friendly and helpful. Everything is well taken care of.

Reviewed on 9 Jun 2025

The Churchill Hotel near Embassy Row

The Churchill Hotel near Embassy Row

4 out of 5
Northwest
per person
31 Jul - 7 Aug
found 1 day ago
Return flight included
Lisbon (LIS) to Washington (DCA)
8.8/10 Excellent! (1,777 reviews)
Very nice hotel . 2nd time stayed here and would definitely stay again . Very friendly staff and in great location

Reviewed on 24 Jun 2025

Top hotels in Upperville

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 €246 per night from 30 Jun to 1 Jul
€246
30 Jun - 1 Jul
includes taxes & fees
8.6/10 Excellent! (1,004 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 21 Jun 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 €97 per night from 6 Jul to 7 Jul
€97
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (2,069 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 24 Jun 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 €103 per night from 5 Jul to 6 Jul
€103
5 Jul - 6 Jul
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 22 Jun 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.

Frequently asked questions

How much does an Upperville holiday package cost?
You can snap up a holiday package to this popular destination from €923 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.

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