Winchester Holidays from AU$485
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Your Winchester Holiday
Lock in a Winchester holiday package and focus on what matters — enjoying yourself. This means no more planning stresses, just more free time to experience the best of this captivating city, such as its rich history and small-town feel. Want to explore? Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall are a few of the best places to visit during your trip to Winchester. No matter your travel plans or the size of your budget, organising a tailored Winchester holiday is a cinch with Expedia.
The Latest Winchester Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Eurostars Saint Gregory Dupont Circle Georgetown
Downtown Washington D.C.
Save 100% on your flight
Price was AU$1,059, price is now AU$690 per person
AU$690
per person
7 Jan - 10 Jan
found 7 hours ago
Return direct flight included
Orlando (MCO) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
The staff especially Marcus & Noam, the valet. I hope I spelled that correctly.
Reviewed on 20 Nov 2025
Salamander Washington DC
Southwest
Save 100% on your flight
Price was AU$1,165, price is now AU$833 per person
AU$833
per person
7 Jan - 10 Jan
found 7 hours ago
Return direct flight included
Orlando (MCO) to Washington (DCA)
9.4/10 Exceptional! (1,021 reviews)
We had an amazing experience to stay with family. Thank you for your great service.
Reviewed on 1 Dec 2025
The Watergate Hotel
Northwest
Price was AU$942, price is now AU$722 per person
AU$722
per person
7 Jan - 10 Jan
found 7 hours ago
Return direct flight included
Orlando (MCO) to Washington (DCA)
8.8/10 Excellent! (1,059 reviews)
As always, the staff at the Watergate is warm and welcoming. The rooms are immaculate and the food is amazing.
Reviewed on 2 Dec 2025
Winchester Holiday
Winchester Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 27,300 |
Max Temp Winter | 4ºC |
Max Temp Summer | 29ºC |
Top Sights | Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre |
Our pick of the best Winchester Hotel Deals
Travelodge by Wyndham Winchester
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$113 per night from 7 Dec to 8 Dec
AU$113
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (1,097 reviews)
Was congratulating myself on having chosen a nice, clean, simple place charging only $15 fee for each of my pets. Nice layout, smooth check in, pleasant staff. Until my better half pointed out the animal feces, dried and obviously a long-term resident, next to the bedside chair. Ed always leave tips ...
Reviewed on 27 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 AU$153 per night from 4 Dec to 5 Dec
AU$153
4 Dec - 5 Dec
includes taxes & fees
9.2/10 Wonderful! (2,235 reviews)
Holiday weekend no breakfast you want to eat
Reviewed on 27 Nov 2025
Microtel Inn & Suites by Wyndham Winchester
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 16 Dec to 17 Dec
AU$119
16 Dec - 17 Dec
includes taxes & fees
9/10 Wonderful! (1,371 reviews)
Room and public areas were very clean and well taken care of.
Reviewed on 26 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
