Winchester Holidays from £712

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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

Price found within the past 48 hours. Click for updated prices.
YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
12 Jul - 15 Jul
Return direct flight included
London (LON) to Washington (DCA)
8.4/10 Very Good! (1,414 reviews)
Very clean. Staff are very thoughtful and helpful.

Reviewed on 1 May 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
per person
17 Jun - 21 Jun
Return direct flight included
London (LHR) to Washington (DCA)
8.8/10 Excellent! (1,300 reviews)
Just perfect for dc

Reviewed on 23 Apr 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
per person
12 Jul - 15 Jul
Return direct flight included
London (LON) to Washington (DCA)
9.4/10 Exceptional! (1,226 reviews)
The location is exceptional. The staff went above and beyond with all services.

Reviewed on 30 Apr 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
12 Jul - 15 Jul
Return direct flight included
London (LON) to Washington (DCA)
8.8/10 Excellent! (1,952 reviews)
I stayed for 3 days, never had housekeeping come. I asked for towel, the man had an attitude with me. Otherwise the place was great. I always tip housekeeping, not this time

Reviewed on 24 Apr 2024

Capitol Hill Hotel

Capitol Hill Hotel

4 out of 5
Capitol Hill
per person
12 Jul - 15 Jul
Return direct flight included
London (LON) to Washington (DCA)
9/10 Wonderful! (1,009 reviews)
Good location for our trip purposes quiet safe close to the metro Housekeeping comes very late in the day Breakfast ok had to leave the building to go to another building Resort fee - don’t see the need for it

Reviewed on 28 Apr 2024

Salamander Washington DC

Salamander Washington DC

5 out of 5
Southwest
per person
12 Jul - 15 Jul
Return direct flight included
London (LON) to Washington (DCA)
9.2/10 Wonderful! (1,019 reviews)
This property was amazing - the hotel itself, the view, and the proximity to everything was absolutely perfect. We’ll definitely be back to see the difference with the new renovations!

Reviewed on 30 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

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! (1,056 reviews)
"Very nice"

Reviewed on 30 Apr 2024

Travelodge 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! (1,292 reviews)
Great place to stay
"A very nice place to stay. We loved the fact that it was fast and easy to get checked in and that they welcomed our dog. We have a larger dog, and many hotels won't accept her. The room was great and so was the breakfast the next day. Will definitely stay here again."

Reviewed on 29 Apr 2024

La Quinta Inn & Suites by Wyndham Winchester
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! (739 reviews)
"This property is brand new…very modern…great breakfast in a bright & clean space"

Reviewed on 30 Apr 2024

Microtel Inn & Suites by Wyndham Winchester
See all 1,887 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.