Winchester Holidays from £830

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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.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
Price was £1,244, price is now £830 per person
£830
per person
26 Sept - 1 Oct
found 21 hours ago
Return direct flight included
Birmingham (BHX) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
Good location, friendly staff, great breakfast, clean and quiet rooms, best sleep in a week

Reviewed on 12 Aug 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Price was £1,450, price is now £978 per person
£978
per person
26 Sept - 1 Oct
found 21 hours ago
Return direct flight included
Birmingham (BHX) to Washington (WAS)
9.8/10 Exceptional! (28 reviews)
Accommodating staff,professional,pleasant. Clean,I’d stay again!

Reviewed on 20 Aug 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was £1,433, price is now £982 per person
£982
per person
26 Sept - 1 Oct
found 21 hours ago
Return direct flight included
Birmingham (BHX) to Washington (WAS)
9/10 Wonderful! (1,010 reviews)
Everything was great

Reviewed on 15 Aug 2025

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was £1,312, price is now £922 per person
£922
per person
26 Sept - 1 Oct
found 21 hours ago
Return direct flight included
Birmingham (BHX) to Washington (WAS)
9.4/10 Exceptional! (1,012 reviews)
The Wharf is a beautiful area of DC. This hotel is very nice, fancy yet understated. Our room was clean, large and comfortable. Valet parking was a plus. Walkable to great restauranta and to The Anthem. A great concert venue. Our stay was lovely.

Reviewed on 18 Aug 2025

Kimpton Hotel Monaco Washington DC by IHG

Kimpton Hotel Monaco Washington DC by IHG

4.5 out of 5
Downtown Washington D.C.
Save 100% on your flight
Price was £1,823, price is now £1,322 per person
£1,322
per person
11 Oct - 17 Oct
found 16 hours ago
Return direct flight included
London (LHR) to Washington (WAS)
8.6/10 Excellent! (1,005 reviews)
The room with a queen bed we stayed in was by far the smallest hotel room we've ever stayed in. A bigger person would not have been able to fit between the foot of the bed and the opposite wall (where the TV is mounted), in order to move from the side of the room with the door and bathroom to the side with the desk and most readily accessible outlets. The place was clean, but our room was located on the "1st" floor, which is sub street level (and below the lobby) and smelled musty. The room itself actually smelled damp. We considered asking for a different room, but the schedule for the convention we were in town for was tight, so we just dealt with it for the hours we were in the room to sleep. The food at the restaurant is good, the staff is very polite, and I appreciate that they highlight the automatic gratuity on the check. I found it a little strange that, though they walk by the tables frequently, you essentially have to flag someone down to ask for the check, a to go box, etc. No one ever even stopped in to check on my meal or ask if I wanted water.

Reviewed on 15 Aug 2025

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

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 £83 per night from 7 Sept to 8 Sept
£83
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (2,133 reviews)
"Just a suggestion. I am disabled and was placed in a lovely room on the 6th floor. The fire alarm went off and my concern is how is someone in a wheelchair going to evacuate without the elevator. Maybe all ada rooms shou"

Reviewed on 19 Aug 2025

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
Fully refundableReserve now, pay when you stay
The price is £64 per night from 15 Sept to 16 Sept
£64
15 Sept - 16 Sept
includes taxes & fees
9/10 Wonderful! (1,321 reviews)
Great quick stay!
"Hotel is brand new, clean and the staff is lovely. The beds are a bit hard and the breakfast was just ok. The gym was great."

Reviewed on 18 Aug 2025

Microtel Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is £68 per night from 7 Sept to 8 Sept
£68
7 Sept - 8 Sept
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Bed comfort"

Reviewed on 12 Aug 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 1,985 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.
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Popular places to visit

Winchester Medical Center

If Winchester Medical Center is what brings you to town, hopefully you'll have a chance to explore more of Winchester.

Winchester Medical Center

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.

Apple Blossom Mall

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.

Shenandoah Valley Discovery Museum

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.