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Holidays to Winchester

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Accommodation, flights, car rentals, things to do and more - for your holiday in Winchester choose Expedia! Find everything you need to organise your trip to Winchester in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

The George Washington Hotel, A Wyndham Grand Hotel
The George Washington Hotel, A Wyndham Grand Hotel
3.5 out of 5
103 E Piccadilly St, Winchester, VA
The price is £79 per night from 2 May to 3 May
Located in the heart of Winchester, this spa hotel is within a 10-minute walk of Handley Regional Library and Shenandoah Valley Discovery Museum. Winchester ...
4.6/5Exceptional! (984 reviews)
"Lovely room, great bathroom. Hotel was woefully understaffed for breakfast though."

Reviewed on 17 Apr 2021

The George Washington Hotel, A Wyndham Grand Hotel
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
The price is £74 per night from 25 Apr to 26 Apr
Situated in a regional park, this hotel is within 1 mile (2 km) of Valley Health, Shenandoah University and Apple Blossom Mall. Winchester-Frederick County Convention ...
4.3/5Excellent! (982 reviews)
"Beautiful, clean, great bed. Pretty new facility. Absolutely love Winchester. Totally a gem in Va.."

Reviewed on 14 Apr 2021

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn & Suites Front Royal Blue Ridge Shadows, an IHG Hotel
Holiday Inn & Suites Front Royal Blue Ridge Shadows, an IHG Hotel
3 out of 5
111 Hospitality Drive, Front Royal, VA
The price is £90 per night from 28 Apr to 29 Apr
Situated in Front Royal, this golf hotel is 0.6 mi (1 km) from Blue Ridge Shadows Golf Club and 3.1 mi (5 km) from Jackson's Chase Golf Course. Warren Memorial ...
4.5/5Wonderful! (741 reviews)
"Very clean - nice rooms. Google GPS takes you to the wrong address."

Reviewed on 10 Apr 2021

Holiday Inn & Suites Front Royal Blue Ridge Shadows, an IHG Hotel
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.

Top things to do in Winchester

Plan your Winchester holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Winchester. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
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*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions

If I'm not able to travel, can I cancel my Winchester holiday package?
Because we understand life can be unpredictable, the answer is yes. To learn more, visit our Customer Service Portal. But generally speaking, if you’ve booked your Winchester holiday package in the last 24 hours, you may be able to cancel or change it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
What are the top hotels in Winchester?
Travellers journeying to Winchester often make a reservation at Quality Inn Stephens City-Winchester South or Holiday Inn Express Winchester South-Stephens City. You’ll find them in Stephens City. Another happening neighbourhood is White Post. L’Auberge Provencale and L Auberge Provencale Bed and Breakfast are recommended options in this part of town.
When is the best time of year to visit Winchester?
If you enjoy the buzz of peak season, you’ll enjoy visiting Winchester in July, June, May. If you’re after a calmer vibe, January , November, December is the ideal time for you. Don’t want to spend an arm and a leg? You might want to avoid September, when things like hotels and airfares go up in price. April is generally when you’ll score the best deals.
How far in advance should I book my Winchester holiday?
While not all airlines release tickets early, you can usually start comparing international airfares on Expedia up to a year in advance. This is the time you can bag some incredible bargains. If you’re booking late, you might still be in luck. Low prices occasionally become available a few weeks before departure.
What should I know before booking a Winchester travel package?
A travel package can be easier on the wallet than separately booking all you need for your escape. For example, combine your hotels, flights and rental cars and save a pretty penny. Whatever kind of holiday you’re planning, you’re bound to find a package that suits your budget.
Does Expedia offer Book Now, Pay Later Winchester holiday packages?
If your need to travel has arisen suddenly, Expedia can help take the financial load off your shoulders. Working with online lender Affirm, we offer a Book Now, Pay Later solution for all package bookings. It’s easy to set up a payment plan for your travel that works for you.