Winchester Holidays from £609

Book a Hotel + Flight or Car together to unlock savings

Photo by Betsy Wood

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

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
Price was £1,036, price is now £609 per person
£609
per person
1 Oct - 8 Oct
found 1 day ago
Return flight included
London (LHR) to Los Angeles (LAX)
8.6/10 Excellent! (115 reviews)
Will stay again soon

Reviewed on 20 Aug 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
Price was £1,625, price is now £895 per person
£895
per person
19 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Los Angeles (LAX)
8.4/10 Very Good! (1,002 reviews)
I liked the location and the room itself was fine. My only complaint was the hotel had an offputting scent (wet carpet/wet dog). I can't really describe it and it unfortunately made my stay less enjoyable.

Reviewed on 19 Aug 2025

Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

5 out of 5
Wilshire Montana
Save 100% on your flight
Price was £2,992, price is now £1,688 per person
£1,688
per person
19 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Los Angeles (LAX)
9.2/10 Wonderful! (461 reviews)
Oceana was the perfect hotel to spend on the last leg of my trip in LA. We relaxed by the pool and walked along the beach. It's quiet and the rooms are very spacious. The design is very pleasing to the eye. Everyone was friendly and professional - special thanks to Hakeem, Leonard, and Daniel. We will be back.

Reviewed on 19 Aug 2025

Hotel Maya

Hotel Maya

4 out of 5
Save 100% on your flight
Price was £1,390, price is now £813 per person
£813
per person
1 Oct - 8 Oct
found 1 day ago
Return flight included
London (LHR) to Long Beach (LGB)
8.4/10 Very Good! (1,744 reviews)
They didn’t have any towels for the pool, and the restaurant closed early on our stay, but the property is beautiful. Definitely would stay again.

Reviewed on 18 Aug 2025

Fairmont Miramar Bungalows

Fairmont Miramar Bungalows

5 out of 5
Wilshire Montana
Save 100% on your flight
Price was £2,881, price is now £1,698 per person
£1,698
per person
19 Sept - 25 Sept
found 1 day ago
Return direct flight included
London (LON) to Los Angeles (LAX)
7.4/10 Good! (11 reviews)
My son and I enjoyed our trip very much! What a beautiful and private space.

Reviewed on 6 Jun 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 £120 per night from 3 Sept to 4 Sept
£120
3 Sept - 4 Sept
includes taxes & fees
8.6/10 Excellent! (3,751 reviews)
"Had a great time"

Reviewed on 19 Aug 2025

Pala Casino Spa And Resort
Pala Mesa Golf Resort

Pala Mesa Golf Resort

3.5 out of 5
2001 Old Highway 395, Fallbrook, CA
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (628 reviews)
Lovely and relaxing escape!
"We have been coming to this resort for events and to the restaurant for years. This was my first experience with the hotel portion and I was very pleasantly surprised. The rooms overlook the golf course as yet are very private given their proximity to the forested part. The rooms were large, clean, ..."

Reviewed on 15 Aug 2025

Get rates
Pala Mesa Golf Resort
South Coast Winery Resort and Spa

South Coast Winery Resort and Spa

4 out of 5
34843 Rancho California Rd, Temecula, CA
The price is £207 per night from 25 Aug to 26 Aug
£207
25 Aug - 26 Aug
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"The beautiful winery and restaurant"

Reviewed on 20 Aug 2025

South Coast Winery Resort and Spa
See all 1,513 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.