Winchester Holidays from £718

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Your Winchester Holiday

From its rich history to its spectacular views and beyond, there's loads to like about Winchester. Discover the wonders of this interesting city with a Winchester holiday package that's made for you. You'll want to do a little exploring during your trip to Winchester. Don't miss major attractions such as Menifee Lakes Golf Course, Diamond Valley Lake Marina and Western Science Centre. Don't put off your visit to this city any longer. Your dream Winchester holiday is a couple of clicks away with Expedia.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
per person
11 Aug - 18 Aug
found 17 hours ago
Return flight included
London (LHR) to Los Angeles (LAX)
8.6/10 Excellent! (61 reviews)
What a unique little gem of a property! The rooms are small, but clean and well-decorated. The self-check in kiosk with a virtual desk clerk was new to me, but check in went very smoothly.

Reviewed on 1 Jul 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
per person
14 Aug - 20 Aug
found 3 hours ago
Return flight included
London (LHR) to Los Angeles (LAX)
8.4/10 Very Good! (1,004 reviews)
Loved most of it, the only complaint is the parking is expensive for not being on site, but not too bad, across the street, underground.

Reviewed on 1 Jul 2025

The Maybourne Beverly Hills, Maybourne

The Maybourne Beverly Hills, Maybourne

5 out of 5
Save 100% on your flight
per person
20 Aug - 27 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Los Angeles (LAX)
9.8/10 Exceptional! (245 reviews)
The property was beautiful and the rooms are luxurious. The food and amenities are exceptional. The service was outstanding.

Reviewed on 8 Jun 2025

Fairmont Century Plaza Gold Experience

Fairmont Century Plaza Gold Experience

5 out of 5
Century City
Save 100% on your flight
per person
20 Aug - 27 Aug
found 1 day ago
Return direct flight included
Manchester (MAN) to Los Angeles (LAX)
9.8/10 Exceptional! (111 reviews)
I just loved our stay at Fairmont Century Plaza. We will certainly return when we next visit LA. Gorgeous hotel, with a true luxury feel throughout.

Reviewed on 14 May 2025

Fairmont Miramar Hotel

Fairmont Miramar Hotel

5 out of 5
Wilshire Montana
Save 100% on your flight
per person
17 Aug - 24 Aug
found 1 day ago
Return flight included
London (LHR) to Los Angeles (LAX)
8.4/10 Very Good! (1,008 reviews)
Beautiful property, nicely appointed rooms and very friendly staff in all aspects.

Reviewed on 3 Jul 2025

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
San Bernardino, CA (SBD-San Bernardino Intl.)
Population
2,500
Max Temp Winter
18ºC
Max Temp Summer
32ºC
Top Sights
Wilson Creek Winery, Ponte Winery and Mulligan Family Fun Centre

Top hotels in Winchester

Pala Casino Spa And Resort
Pala Casino Spa And Resort
4 out of 5
11154 Highway 76, Pala, CA
Fully refundableReserve now, pay when you stay
The price is £116 per night from 30 Jul to 31 Jul
£116
30 Jul - 31 Jul
includes taxes & fees
8.6/10 Excellent! (3,491 reviews)
"Nice rooms, very clean and spacious"

Reviewed on 2 Jul 2025

Pala Casino Spa And Resort
Signature Temecula
Signature Temecula
3 out of 5
28980 Old Town Front St., Temecula, CA
Fully refundableReserve now, pay when you stay
The price is £58 per night from 14 Jul to 15 Jul
£58
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (1,467 reviews)
"Everything was good, clean decent place, the only thing I didn’t like that much was the continental breakfast, just because they don’t serve eggs and maybe sausage or something other then just sweets, but other then that I love the place."

Reviewed on 1 Jul 2025

Signature Temecula
South Coast Winery Resort and Spa
South Coast Winery Resort and Spa
4 out of 5
34843 Rancho California Rd, Temecula, CA
Fully refundableReserve now, pay when you stay
The price is £270 per night from 18 Jul to 19 Jul
£270
18 Jul - 19 Jul
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Room smelled a tiny bit musty, A/C controls weren't working, Keurig machine didn't work."

Reviewed on 2 Jul 2025

South Coast Winery Resort and Spa
See all 1,511 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 plan your next big adventure easily and all in one convenient place. Our top tip for landing a terrific deal on a Winchester retreat? Bundle your hotel, flights and/or car hire into a package holiday. Then add a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to stress if you have to change your travel plans. Round-the-clock help with amending and cancelling your trip is available via our Customer Service Portal link.
When is the best time of year to holiday in Winchester?
Love sightseeing but don't like queuing up for attractions? Plan your Winchester escape for April, October and December. Typically, it's much quieter than it is in January, February and November. Arrange your trip to Winchester based on what kind of adventure you're looking for. January is the coolest month, when average daytime temperatures are 10ºC. In August, the warmest month, you can expect averages of 25ºC during the day.
What is the top hotel for my holiday in Winchester?
Relax in comfort in Winchester by choosing Best Western Plus Las Brisas Hotel as your home base and gateway to exploration and adventure.
How do I get a cheap holiday to Winchester?
Booking a Winchester holiday with Expedia is a great way to save. We have more than 400 air carriers and 321,000 hotel options globally. With such an extensive range to pick from, you'll have no hassles putting together your dream holiday. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Winchester holiday?
With must-see tourist attractions such as Diamond Valley Lake Marina and Menifee Lakes Golf Course, a holiday in Winchester promises lots of fun things to do and see. Orange Empire Railroad Museum and Skydive Perris are a couple of other sights worth discovering.
Do I need a visa for my Winchester holiday?
Official government websites will have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and reason for travelling, whether it be for tourism or business, will determine if you need a visa for Winchester. Also make sure your passport is up to date and has a minimum of six months validity remaining beyond your date of return. Finalise all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Winchester holiday?
First, consider the types of activities you'll be doing during your holiday in Winchester and bring versatile pieces that can be mixed and matched. For fashion inspiration or information on any dress codes, look up a few style blogs or social media accounts. Pack your luggage with confidence by checking the weather forecast in Winchester. August brings the warmest temperatures, with daily averages of 25ºC, while January days average 10ºC, making it the coolest time of year.
What does an Expedia Winchester holiday include?
Expedia has all you need to arrange your Winchester getaway, but how you structure your package is your choice. Pick from a combination of flights, hire cars and hotels. Looking for some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package to suit your needs. Discover a wide range of property types and choose one that fits the size of your group. The most sought-after holiday rentals here are private holiday homes and apartments. With Expedia, it's easy to tailor-make your Winchester escape however you like.
Does Expedia offer Book Now, Pay Later Winchester holidays?
We certainly do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply click on the payment plan that suits you best during checkout and take away the stress of budgeting for your trip. Don't forget to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your buck. Take a look at our flexible payment options below:

  • Pay monthly holidays: Klarna offers the ability to pay in multiple transactions that suit all types of budgets, so you can escape on that well-deserved holiday now.
  • No-deposit holidays: Hitting the "book now" button is much easier with this payment plan. With no deposit required for your escape, you can Book Now, Pay Later and start packing your suitcase.

Can I choose my airline with a Winchester Expedia holiday?
With a holiday package, you're in charge. Whether you're eager to fly to Winchester in business or coach, simply pick from the available airline options. Expedia has access to over 400 partner airlines throughout the world.

* 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.