Upperville Holidays

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    Better together
    Save up to S$134 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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    Plan, book, and manage your trip all in one place
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
Unlock Black Friday deals

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 S$142 per night from 3 Dec to 4 Dec
S$142
includes taxes & fees
3 Dec - 4 Dec
9/10 Wonderful! (1,726 reviews)
"Easy check in"

Reviewed on 25 Nov,2024

La Quinta Inn & Suites 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 S$311 per night from 26 Nov to 27 Nov
S$311
includes taxes & fees
26 Nov - 27 Nov
8.4/10 Very Good! (965 reviews)
"I liked everything about this property. From the front door - valet parking; even though we didn’t use it, the valet workers still came to the car to assist us with our belongings. We received a smile and welcome from everyone! The reception staff were excellent. They took the time to explain the ..."

Reviewed on 25 Nov,2024

Lansdowne Resort and Spa
Salamander Resort And Spa
Salamander Resort And Spa
5 out of 5
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is S$914 per night from 26 Nov to 27 Nov
S$914
includes taxes & fees
26 Nov - 27 Nov
9/10 Wonderful! (322 reviews)
Beauty and Elegance in Horse Country
"Fantastic property and top tier customer service. Everything was 5 star from the accommodations to the exquisite cuisine and wine"

Reviewed on 16 Nov,2024

Salamander Resort And Spa
See all 674 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?
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.