Upperville Holidays from £748

Book a Hotel + Flight or Car together to unlock savings

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    Save up to £335 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Your Upperville Holiday

When you choose a Upperville holiday 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 holiday to Upperville to match your travel style, whatever that may be.

The Latest Upperville Holiday 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
3 Sept - 9 Sept
found 21 hours ago
Return direct flight included
Glasgow (GLA) 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 19 Jun 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
9 Sept - 14 Sept
found 1 day ago
Return direct flight included
London (LHR) to Washington (DCA)
No 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 22 Jun 2025

Crowne Plaza Crystal City-Washington, D.C. by IHG

Crowne Plaza Crystal City-Washington, D.C. by IHG

3.5 out of 5
Crystal City
per person
3 Sept - 9 Sept
found 21 hours ago
Return direct flight included
Glasgow (GLA) to Washington (DCA)
8.2/10 Very Good! (1,006 reviews)
Property was well kept. Staff was courteous and helpful. Breakfast was above average in selection and quality. Location to the Metro was within walking distance {about a block and a half. Overall a great value and pleasant stay.

Reviewed on 22 Jun 2025

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
3 Sept - 9 Sept
found 21 hours ago
Return direct flight included
Glasgow (GLA) to Washington (DCA)
9.4/10 Exceptional! (1,477 reviews)
My husband and I stayed there with our 2 boys and we had a great! We flew in from Texas and didn’t know if this area would be good as far as walking distance to the main attractions (White House, Washington monument etc) but we managed it all just fine. The hotel was lovely, clean, comfy, the staff was so nice & helpful! Places to eat close by within a 10min walk. (We did not rent a car, we walked everywhere and or Uber’d in the evening once we were done - all the Ubers/Taxi knew where the hotel was so it was quick) The ONLY issue we had was the shower - it wouldnt get to an in between of warm and hot and so after a long day of touring DC ( & walking everywhere) a nice warm shower is what we all wanted and we couldn’t get it just right but once we did, it took forever & we’d have to be quick once it finally got to a temp we wanted.

Reviewed on 20 Jun 2025

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
15 Sept - 20 Sept
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.8/10 Exceptional! (944 reviews)
We try to stay at different properties each time we’re in DC. We’ll be hard-pressed to find one that is better than the Jefferson. The rooms sparkled, the staff were incredibly helpful, the amenities were spot-on, and the location was great.

Reviewed on 26 May 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
3 Sept - 9 Sept
found 21 hours ago
Return direct flight included
Glasgow (GLA) to Washington (DCA)
8.8/10 Excellent! (1,004 reviews)
Sofitel Hotel is in the perfect spot in DC. It’s only a 30 min walk from every attraction. The hotel was clean and everyone was very helpful.

Reviewed on 22 Jun 2025

Upperville Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Washington Dulles Intl. Airport (IAD)
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Barrel Oak Winery, The Boxwood Winery and Philip Carter Winery

Our pick of the best Upperville Hotel Deals

Lansdowne Resort and Spa
Lansdowne Resort and Spa
4 out of 5
44050 Woodridge Pkwy, Leesburg, VA
Stay at this 4-star golf resort in Leesburg. Enjoy an outdoor pool, a golf course and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.6/10 Excellent! (1,002 reviews)
"Nice experience"

Reviewed on 20 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
Stay at this 3-star business-friendly hotel in Winchester. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
9/10 Wonderful! (2,057 reviews)
"Very good!"

Reviewed on 21 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
Stay at this 3-star business-friendly hotel in Ashburn. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.4/10 Very Good! (1,002 reviews)
"Convient"

Reviewed on 19 Jun 2025

Hilton Garden Inn Dulles North
See all 711 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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does an Upperville travel package cost?
Chart your own course with our Upperville travel packages, which start from just £748. Pick the flights and hotels that suit your travel plans. Then, add on some activities or tours for a memorable escape.
If I'm not able to travel, can I cancel my Upperville travel package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or amend your Upperville travel package at no cost within 24 hours of booking. However, you may incur a fee from your hotel, airline or car rental company for older bookings. If life gets in the way of your holiday, browse our Customer Service Portal for further information.
How do I get a cheap travel package to Upperville?
Bundle, bundle, bundle. Flights, rental cars and hotels --- combine whatever you need into an Upperville travel package to save a ton of cash. Score even more deals when you add extras such as day tours to your booking. But that's not the only impressive part. You have the flexibility to put together your holiday your own way. We offer more than 550 airlines and 1,000,000 hotels worldwide, so that everyone has an opportunity to travel and fulfil those holiday fantasies.
Does Expedia offer Book Now, Pay Later Upperville holidays?
Expedia has joined forces with online lender Klarna to make booking your next break a little easier on the wallet. Paying in instalments means you can spread the costs of your dream holiday, leaving you with more money to play with while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits into your budget. Take a look at these flexible payment options:
  • Pay monthly holidays: Jet off on that dream holiday sooner with Klarna's monthly instalment plans. If paying just a little each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it possible to pay for your trip over multiple transactions.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, consider a low deposit holiday payment plan with Klarna.

What are the top hotels in Upperville?
Make a reservation at Red Roof Inn Warrenton. It's one of this neighbourhood's most popular hotels. Another top-rated option in Upperville is Baymont by Wyndham Warrenton.
How far in advance should I book my Upperville holiday?
Travellers are normally able to look up international airfares on Expedia up to a year in advance of departure. Booking last minute? With a bit of luck, it's still possible to score a cheaper ticket only weeks before your flight.
What does an Expedia Upperville travel package include?
Choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like tours and activities. Want to pick your airfare class? That's easy to do too. The choice is all yours when it comes to crafting your dream Upperville trip.
What should I know before booking an Upperville travel package?
Our prices are always low. However, you'll pick up even more savings when you book your hotels, flights and car rentals together. With an Expedia package, you'll get transparent pricing and a great range of choice.
Can I choose my airline with an Upperville Expedia travel package?
Yes, the choice is all yours. We offer more than 550 partner airlines across the globe, so you can customize your Upperville escape according to your style and budget.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.