Winchester Holidays from £1,130
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Your Winchester Holiday
The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester holiday package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organising your ultimate tailored Winchester holiday is easy with Expedia.
Top Winchester Flight + Hotel Deals
Hampton Inn & Suites Washington DC-Navy Yard
Reviewed on 7 Feb 2026
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 |
Top hotels in Winchester
La Quinta Inn & Suites by Wyndham Winchester
Clean, bright, and up-to-date hotel. Friendly staff, warm pool, nice little exercise room. Standard hotel breakfast fare, but it was good, and staff was very kind about the bit of mess our toddlers made while eating (we offered to tidy up, and they said it was no problem!). Great experience.
Reviewed on 31 Jan 2026
Travelodge by Wyndham Winchester
Room was great and breakfast was ok but had waffles
Reviewed on 2 Feb 2026
The George Washington Hotel, A Wyndham Grand Hotel
Clean nice room Great location for restaurants
Reviewed on 28 Jan 2026
Popular places to visit
ValleyHealth Winchester Medical Center
If ValleyHealth Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.
Apple Blossom Mall
You can search for that perfect souvenir at Apple Blossom Mall during your stay in Winchester. While in this walkable area, you can savour the top-notch restaurants.
Shenandoah Valley Discovery Museum
You can take time to visit Shenandoah Valley Discovery Museum during your travels to Winchester. While in this walkable area, you can savour the top-notch restaurants.
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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. Flight-inclusive packages are ATOL protected.
