Upperville Holidays
Book a Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
Better together
Save up to NZ$616 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
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Plan, book, and manage your trip all in one place
Upperville Holiday
Our pick of the best Upperville Hotel Deals
La Quinta Inn & Suites by Wyndham Winchester
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 29 Sept to 30 Sept
NZ$201
29 Sept - 30 Sept
includes taxes & fees
9.2/10 Wonderful! (2,152 reviews)
"Easy access to the highway as we passed through."
Reviewed on 13 Sept 2025
Salamander Resort And Spa
500 North Pendleton Street, Middleburg, VA
Fully refundableReserve now, pay when you stay
The price is NZ$1,207 per night from 5 Oct to 6 Oct
NZ$1,207
5 Oct - 6 Oct
includes taxes & fees
9/10 Wonderful! (363 reviews)
"Lovely restful 2 days Unable to book massage and facial they are fully booked. I was told they are booked months in advance."
Reviewed on 28 Aug 2025
Lansdowne Resort and Spa
44050 Woodridge Pkwy, Leesburg, VA
Fully refundableReserve now, pay when you stay
The price is NZ$487 per night from 30 Sept to 1 Oct
NZ$487
30 Sept - 1 Oct
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"One of the best in town Clean and modern"
Reviewed on 17 Sept 2025
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.
More holiday ideas
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
