Winchester Holidays from £1,364

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Your Winchester Holiday

Lock in a Winchester holiday package and get ready for a thrilling getaway. Known for its rich history and small-town feel, there's lots to keep you on the go in this interesting city. Any trip to Winchester needs a well-designed itinerary. Fill yours with major attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whoever you're taking time off with and whatever you plan to spend, your ultimate Winchester holiday is only clicks away with Expedia.

The Latest Winchester Holiday Deals

Prices and availability subject to change. Additional terms may apply.
Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,226 reviews)
Great location. Comfortable. Pricy.

Reviewed on 23 Apr 2024

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Washington (DCA)
8.4/10 Very Good! (1,414 reviews)
My room, 1055, was cleaned daily. Staff was professional, courteous and helpful.

Reviewed on 20 Apr 2024

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Washington (DCA)
8/10 Very Good! (1,000 reviews)
The shuttle to/from Union station was very convenient. Overall a great place to stay - highly recommend!

Reviewed on 17 Apr 2024

The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel

The Ven at Embassy Row, Washington, D.C., a Tribute Portfolio Hotel

4 out of 5
Northwest
per person
15 Jul - 18 Jul
Return flight included
London (LON) to Washington (DCA)
8.8/10 Excellent! (298 reviews)
I would have given this hotel 5 stars if the a/c / heating system did not sound like a jetliner engine. Seriously, it was the LOUDEST noise I had ever heard in any hotel I have stayed at. We had to turn off the a/c and open the windows. Thank goodness the guest in the unit above us did the same because we couldn't go to sleep hearing the "jet roar" of their a/c unit. Until the systems are updated, BRING SILICON EARPLUGS for book elsewhere.

Reviewed on 20 Apr 2024

Lyle Washington D.C.

Lyle Washington D.C.

4.5 out of 5
Northwest
per person
15 Jul - 18 Jul
Return flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,259 reviews)
Staff was outstanding, very helpful and accommodating.

Reviewed on 23 Apr 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
12 Jun - 15 Jun
Return flight included
London (LON) to Washington (DCA)
9/10 Wonderful! (1,003 reviews)
Very nice hotel in a very convenient location. However, the room attendant and restaurant/bar staff were not attentive, long waits and food quality suspect.

Reviewed on 22 Apr 2024

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

Microtel Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
2.5 out of 5
150 Faraday Plaza, Winchester, VA
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (726 reviews)
"Great hotel! Staff is excellent and rooms are clean."

Reviewed on 24 Apr 2024

Microtel Inn & Suites by Wyndham Winchester
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
Stay at this business-friendly hotel in Winchester. Enjoy free breakfast, free WiFi and free parking. Our guests praise the pool and the helpful staff in their ...
8.8/10 Excellent! (1,278 reviews)
"Nicer hotel. Felt safe and was clean. The check in clerk was okay but quick and brusk with instructions. Not overly friendly. She was more interested in another employee who was trying to talk with her at the same time."

Reviewed on 23 Apr 2024

La Quinta Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Travelodge by Wyndham Winchester
2.5 out of 5
160 Front Royal Pike, Winchester, VA
Stay at this business-friendly motel in Winchester. Enjoy free breakfast, free WiFi and free parking. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (1,054 reviews)
"Very clean and convenient. Building a bit run down and coffee was weak with limited food but that’s about what was expected for the price. I’d stay again"

Reviewed on 23 Apr 2024

Travelodge by Wyndham Winchester
See all 1,878 properties in Winchester
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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Winchester

Image for Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(1 review)

You can spend time browsing the exhibits at Museum of the Shenandoah Valley during your trip to Winchester. Visit the cosy cafes or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Image for Handley Regional Library

Handley Regional Library

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Visit the top-notch restaurants or cosy cafes in this walkable area.

Handley Regional Library
Image for Shenandoah University

Shenandoah University

Enjoy the student vibe when you visit Shenandoah University during your trip to Winchester. While in this walkable area, you can savour the top-notch restaurants.

Shenandoah University

* 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.