Winchester Holidays from £686
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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
Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG
Southwest
£1,303
per person
11 Oct - 17 Oct
found 1 day ago
Return flight included
London (LON) to Baltimore (BWI)
9.4/10 Exceptional! (1,210 reviews)
Everything was wonderful except the mattresses were a little more firm than my wife and I would like. I woke up with back pain each day.
Reviewed on 7 Aug 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
Holiday Inn Winchester Se-Historic Gateway by IHG
333 Front Royal Pike Winchester VA
Fully refundable
£71
12 Aug - 13 Aug
includes taxes & fees
9/10 Wonderful! (1,015 reviews)
"no phone cord for the hotel phone so I couldn't call room to room and there were only 3 bath towels for 4 people but both were easy fixes. But my reservation said free breakfast and they wanted $10 for 2 people, so not sure what that was about"
Reviewed on 7 Aug 2026
Spark by Hilton Winchester
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
£65
6 Sept - 7 Sept
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
"The room was spacious; clean"
Reviewed on 7 Aug 2026
The George Washington Hotel, A Wyndham Grand Hotel
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
£103
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,014 reviews)
"It's hard to pick out one thing that makes the George Washington excellent. Is it the staff? Yes. But is it the ambiance of an historic hotel? Certainly. How about the location? For sure! Can it be the memories of past stays? Oh, yes as we always celebrate our anniversary in Winchester. What about ..."
Reviewed on 7 Aug 2026
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.
Stay near popular Winchester attractions
Museum of the Shenandoah Valley
8.8/10 (129 reviews)
Discover the Shenandoah Valley's rich heritage at this cultural cornerstone. Wander through the historic Glen Burnie House and meticulously designed gardens for a refined afternoon of regional exploration.
Shenandoah University
8.8/10 (276 reviews)
This prestigious Virginia university shines with its acclaimed Conservatory for performing arts and vibrant campus life. Catch a student concert or theatrical production for an enriching cultural experience.
Patsy Cline Historic House
8.4/10 (104 reviews)
Step back in time at the modest four-room house where country music legend Patsy Cline spent her childhood. Tours showcase original furnishings and artefacts, offering glimpses into her journey to stardom.
Apple Blossom Mall
8.2/10 (315 reviews)
Apple Blossom Mall offers over 60 stores and an AMC 12-screen theatre in Winchester's premier shopping destination. Browse fashion retailers, speciality shops, and diverse dining options in this comprehensive retail hub.
Rock Harbor Golf Course
7.6/10 (49 reviews)
Carved from quarry landscapes, Rock Harbour offers two championship golf courses with dramatic elevation changes and water hazards. Navigate the challenging Boulder Course or enjoy the more forgiving Rock Course amid valley vistas.
Bright Box Theater
7.8/10 (18 reviews)
This vibrant venue in Old Town Winchester hosts over 200 live music, comedy, and drag performances annually. Arrive early to secure prime seating and enjoy craft beers and bistro fare before the show begins.
Stonewall Jackson's Headquarters
10.0/10 (1 review)
Step back in time at this Gothic Revival house where Confederate General "Stonewall" Jackson strategized during winter 1861-1862. Explore his artefacts while guides reveal the general's military genius.
Winchester Little Theater
7.6/10 (37 reviews)
This intimate theatre operates in a historic Pennsylvania Railway freight station with original boxcars. Enjoy community productions in a cosy venue where every seat offers a close connection to the performers.
Frequently asked questions
Why should I book my Winchester holiday with Expedia?
Choose Expedia to arrange your next adventure with ease, all in one place. Our insider tip for landing a great deal on a Winchester getaway? Bundle your flights, accommodation and/or hire car into a package holiday. Then throw in some fun tours and activities. Many bookings also have flexible cancellation policies, so there's no need to stress if you have to switch up your travel itinerary. Round-the-clock help with cancelling and amending your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Winchester?
To enjoy the energy of peak season, take off in July, August and October. December, January and February are typically quieter and a good idea if you'd rather escape the crowds. Arrange your getaway to Winchester based on what type of holiday you want. January is the coolest month, when average daytime temperatures are 0ºC. In July, the warmest month, you will experience temperatures of around 24ºC during the day.
What are the top hotels for my holiday in Winchester?
Sleep Inn & Suites will be an excellent base for your Winchester getaway. Situated in Old Town Winchester, it's one of this area's best hotels.
How do I get a cheap holiday to Winchester?
Lock in flights that fit your schedule, add a hotel to your booking and watch the savings rack up with a Winchester holiday. It's as simple as that! From hotels and flights to tours and hire cars, Expedia is where your cheap holiday begins. And with more than 400 partner airlines and 321,000 hotels across the globe to select from, you won't be short of choice. Learn more about how you can save money on your next holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Winchester holiday?
There's an almost endless list of things to explore while enjoying your holiday in Winchester. Shenandoah University, Winchester Medical Centre, Museum of the Shenandoah Valley and Apple Blossom Mall are just some of this city's leading attractions.
What is the best area to stay in when on holiday in Winchester?
There's plenty to do in Winchester, so spend your nights near its top attractions and allow yourself more time sightseeing. Shenandoah University is one place that should be on your itinerary.
Do I need a visa for my Winchester holiday?
Look up the latest rules on official government websites. Your nationality and whether you're visiting for business, study or leisure will determine if you need a visa for Winchester. Find out about the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow enough time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Winchester holiday?
Do some research into the types of clothing people in Winchester wear, and maybe even check out social media fashion pages for inspiration. Whatever your look, aim to create a versatile travel wardrobe full of pieces that work for your destination and showcase your unique style. Daytime temperatures during January, Winchester's coolest month, are around 0ºC. July marks this city's warmest month when the average reaches 24ºC. Our tip? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Winchester holiday include?
Flights, hotels and a shiny set of wheels for all your fun road trip adventures. Simply pick and choose your favourite bundle and get access to great discounts. Once you've made your booking, add on a couple of tours and activities and watch your savings pile up. When it comes to organising your Winchester getaway, you're in charge! Expedia features different types of properties, with the most popular in Winchester including private holiday homes and hotels. With Expedia, you'll always have the flexibility and freedom to customise your holiday however you like.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book your dream getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your trip. Consider one of these flexible payment options:
- Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that work for all budget sizes, so you can have that well-deserved holiday sooner.
- No-deposit holidays: When you spot an amazing deal but your budget doesn't quite cover it yet, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock in your getaway.
Can I choose my airline with a Winchester Expedia holiday?
Yes — and it's simple too. Expedia has access to more than 400 partner airlines worldwide. Our holiday packages give you the flexibility to pick from available flights, hotels and activities that suit you.
* 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.
