Winchester Holidays from £1,032

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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.
Hilton Club The District Washington D.C.

Hilton Club The District Washington D.C.

3.5 out of 5
Downtown Washington D.C.
Price was £1,223, price is now £1,032 per person
£1,032
per person
26 Dec - 31 Dec
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Baltimore (BWI)
9.4/10 Exceptional! (672 reviews)
Shared space with Embassy Suites. Lovely apartment type room and bedroom.

Reviewed on 30 Oct 2026

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
Price was £1,513, price is now £1,132 per person
£1,132
per person
5 Dec - 12 Dec
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
9/10 Wonderful! (1,008 reviews)

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,376, price is now £1,052 per person
£1,052
per person
26 Dec - 31 Dec
found 4 hours ago
Return direct flight included
Edinburgh (EDI) to Baltimore (BWI)
9/10 Wonderful! (1,285 reviews)

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Price was £1,994, price is now £1,644 per person
£1,644
per person
26 Dec - 1 Jan
found 15 hours ago
Return flight included
London (LON) to Baltimore (BWI)
9.8/10 Exceptional! (1,001 reviews)
This hotel is a treasure! The rooms, the staff, the beautiful lobby, and the dining experience are all exceptional!

Reviewed on 31 Oct 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was £2,152, price is now £1,842 per person
£1,842
per person
5 Dec - 12 Dec
found 1 day ago
Return flight included
London (LHR) to Baltimore (BWI)
9.4/10 Exceptional! (1,394 reviews)
Love the Riggs. Gym was great. Loved the restaurant and the speakeasy. The woman at the front desk was so helpful and accommodating. Beds cozy!!

Reviewed on 30 Oct 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

Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike Winchester VA
Fully refundableReserve now, pay when you stay
The price is £58 per night from 1 Dec to 2 Dec
£58
1 Dec - 2 Dec
includes taxes & fees
8.6/10 Excellent! (1,069 reviews)
"Clean room, good staff, good location"

Reviewed on 1 Nov 2026

Travelodge 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
Fully refundableReserve now, pay when you stay
The price is £68 per night from 3 Nov to 4 Nov
£68
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (1,432 reviews)
"Better pillows Also there was tv guide in room"

Reviewed on 31 Oct 2026

Microtel Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East Winchester VA
Fully refundableReserve now, pay when you stay
The price is £90 per night from 3 Nov to 4 Nov
£90
3 Nov - 4 Nov
includes taxes & fees
9.2/10 Wonderful! (2,269 reviews)
"Rooms were spacious, beds were comfortable, coffee and breakfast were only ok"

Reviewed on 1 Nov 2026

La Quinta Inn & Suites by Wyndham Winchester
See all 2,231 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

Stay near popular Winchester attractions

A brick pathway leading to a central lawn area, surrounded by trimmed hedges and trees.
Photo by Tina McClelland
Open Photo by Tina McClelland

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.
See properties

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.