Upperville Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

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

  • 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.

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

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 £57 per night from 1 Dec to 2 Dec
£57
1 Dec - 2 Dec
includes taxes & fees
Travelodge by Wyndham Winchester
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 £175 per night from 25 Nov to 26 Nov
£175
25 Nov - 26 Nov
includes taxes & fees
Lansdowne Resort and Spa
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
The price is £110 per night from 19 Nov to 20 Nov
£110
19 Nov - 20 Nov
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Great hotel in an excellent downtown location only one block from Winchester’s lovely pedestrian-only shopping and dining area. The room was large, clean, and well appointed. A unique and gorgeous bar was great fun."

Reviewed on 11 Nov 2026

The George Washington Hotel, A Wyndham Grand Hotel
See all 747 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

Stay near popular Upperville attractions

Upperville Park

Explore the great outdoors at Upperville Park, a lovely green space in Upperville.
See properties

Frequently asked questions

How much does an Upperville travel package cost?
Chart your own course with our Upperville travel packages, which start from just . 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.