Upperville Holidays
Book a Hotel + Flight or Car together to unlock savings
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- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Upperville Holiday
Our pick of the best Upperville Hotel Deals
Travelodge by Wyndham Winchester
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is NZ$132 per night from 1 Dec to 2 Dec
NZ$132
1 Dec - 2 Dec
includes taxes & fees
8.4/10 Very Good! (1,126 reviews)
Such a great find for our overnight Stay and last minute with excellent price. Comfortable bed and fantastic staff. Breakfast lacking but expected.
Reviewed on 6 Nov 2025
Hilton Garden Inn Dulles North
22400 Flagstaff Plaza, Ashburn, VA
Fully refundableReserve now, pay when you stay
The price is NZ$174 per night from 23 Nov to 24 Nov
NZ$174
23 Nov - 24 Nov
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
Room was clean. Checkin staff was very courteous. Breakfast was not too lavish but decent for the price. So overall we were quite pleased with the stay
Reviewed on 1 Nov 2025
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$204 per night from 10 Dec to 11 Dec
NZ$204
10 Dec - 11 Dec
includes taxes & fees
9.2/10 Wonderful! (2,198 reviews)
Sheets were comfy, towels were a reasonable size, overall would recommend.
Reviewed on 2 Nov 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.
