Upperville Holidays

    Plan, book, travel with confidence
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    Better together
    Save up to €185 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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    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Upperville

La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is €96 per night from 1 Dec to 2 Dec
€96
includes taxes & fees
1 Dec - 2 Dec
9/10 Wonderful! (1,684 reviews)
"Clean and pet friendly, comfy beds, nice staff"

Reviewed on 8 Nov 2024

La Quinta Inn & Suites by Wyndham Winchester
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 €64 per night from 19 Nov to 20 Nov
€64
includes taxes & fees
19 Nov - 20 Nov
8/10 Very Good! (1,119 reviews)
"Nice comfortable room for a fair price"

Reviewed on 8 Nov 2024

Travelodge 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 €76 per night from 19 Nov to 20 Nov
€76
includes taxes & fees
19 Nov - 20 Nov
9/10 Wonderful! (1,031 reviews)
"Very clean and spacious and a very reasonable price."

Reviewed on 6 Nov 2024

Microtel Inn & Suites by Wyndham Winchester
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?
Starting from an incredible , you can handcraft your own Upperville package. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Upperville?
Our Upperville holiday packages mean plenty of savings for the savvy wanderer. For the best deal, simply bundle your flights, hotels and activities into one neat package. But impressive bargains are just the beginning of your next unforgettable adventure. When you book with Expedia, you’ll have more than 550 airlines and 1,000,000 properties around the globe to pick from. Whatever your budget or style, there’s a holiday package with your name on it.
How far in advance should I book my Upperville holiday?
It all depends on the air carrier, but you can normally browse through international airfares on Expedia nearly a year in advance. While it’s generally a good idea to book ahead of time, lucky travellers will sometimes nab a cheaper flight just weeks prior to the date of departure.
What does an Expedia Upperville travel package include?
Expedia has all you need to plan your Upperville getaway, but what goes into your package is totally up to you. Choose from a combination of hotels, rental cars and flights. Looking for some activities to keep you on the go? Once you’ve made your booking, you can add them on too. No matter your budget or style, there’s a package to meet your needs.
What should I know before booking an Upperville travel package?
So many places to visit, so many things to see. With a package, you’ll be able to cross more of them off your list. Bundle your flights, rental cars and hotels and get set to save.
Can I choose my airline with an Upperville Expedia holiday package?
Yes, and with over 550 airlines to select from globally, you’re not short on choice. Look through the available options and see which airline best suits your needs and budget.
If I'm not able to travel, can I cancel my Upperville holiday package?
Plans can change in a flash, so yes, you can. You may be able to cancel or alter your Upperville holiday package for free if you’ve booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We’re here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.