Upperville Holidays from £754

Book a Hotel + Flight or Car together to unlock savings

Photo by Michael Gibson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Packages with flights are ATOL protected

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.

Top Upperville Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
30 Oct - 4 Nov
found 1 day ago
Return direct flight included
London (LHR) to Washington (DCA)
8.6/10 Excellent! (1,005 reviews)
Very well located. Felt safe to walk all times of day and night. Great food spots located all around. Subway not too far from it as well, only like .04 miles from it. Great staff. Will definitely stay there next time I return to D.C

Reviewed on 8 Aug 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return direct flight included
London (LON) to Washington (DCA)
9.8/10 Exceptional! (28 reviews)
Absolutely incredible hotel that we happened upon on a whim. Brand new, absolutely stunning and Johnny the concierge made our night and had us feeling right at home despite the grandeur of the establishment. Can’t recommend this place enough and shout out to Johnny ❤️

Reviewed on 3 Aug 2025

Club Quarters Hotel in Washington DC

Club Quarters Hotel in Washington DC

3 out of 5
Downtown Washington D.C.
per person
14 Oct - 21 Oct
found 3 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
8.8/10 Excellent! (1,624 reviews)
Room is basic but good enough for a short stay if you’re not staying in much. Location is convenient. Service from the staff is lacking. Overall, really good value for the price.

Reviewed on 6 Aug 2025

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
14 Oct - 21 Oct
found 3 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
9.4/10 Exceptional! (1,437 reviews)
The property was extremely quiet. The hotel restaurant for breakfast was awesome.

Reviewed on 6 Aug 2025

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
14 Oct - 21 Oct
found 3 hours ago
Return direct flight included
Birmingham (BHX) to Washington (DCA)
8.8/10 Excellent! (2,579 reviews)
Excellent hotel, clean and comfy bed.

Reviewed on 7 Aug 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

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 £220 per night from 17 Aug to 18 Aug
£220
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"One of the best hotels in city . Modern clean big lots of amenities , great pools"

Reviewed on 6 Aug 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 £83 per night from 7 Sept to 8 Sept
£83
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (2,110 reviews)
"Love the room layout, bathroom is a buffer to minimize noise from hallway. Fitness equipment needs repair"

Reviewed on 5 Aug 2025

La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is £65 per night from 7 Sept to 8 Sept
£65
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,326 reviews)
"Only thing I would change is the shower no pressure in room 309"

Reviewed on 3 Aug 2025

Microtel Inn & Suites by Wyndham Winchester
See all 707 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 £754. 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.