Winchester Holidays from AU$1,892

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Your Winchester Holiday

There's no better way to escape than with one of our holiday packages to Winchester. The rich history and spectacular views are a couple of the compelling reasons to stay in this interesting city. Any trip to Winchester needs a well-crafted itinerary. Fill yours with famous sights like Diamond Valley Lake Marina, Menifee Lakes Golf Course and Western Science Centre. Check out Expedia's wide range of travel options and book your ultimate holiday to Winchester today.

The Latest Winchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Melrose Rooftop Boutique Residences

Melrose Rooftop Boutique Residences

4 out of 5
Fairfax District
per person
17 Oct - 24 Oct
found 1 day ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
8/10 Very Good! (1 review)
Fairmont Miramar Hotel

Fairmont Miramar Hotel

5 out of 5
Wilshire Montana
per person
24 Oct - 28 Oct
found 1 day ago
Return direct flight included
Sydney (SYD) to Los Angeles (LAX)
8.4/10 Very Good! (1,025 reviews)
Lovely views, convenient location.

Reviewed on 4 Aug. 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
per person
17 Oct - 24 Oct
found 1 day ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
8.4/10 Very Good! (1,012 reviews)
It was Beverly Hills… just hard to navigate and a bit underwhelming as far as the hotel is concerned. The parking was a bit odd too.

Reviewed on 31 Jul. 2025

Oceana Santa Monica, LXR Hotels & Resorts

Oceana Santa Monica, LXR Hotels & Resorts

5 out of 5
Wilshire Montana
Save 100% on your flight
per person
19 Sept - 26 Sept
found 1 day ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
9.2/10 Wonderful! (460 reviews)
My only complaints are: There was what appeared to be some sort of vomit or maybe food on the rug in our room. The rugs/carpet in general could use a cleaning or replacing. The pool could be open a bit longer. It closes at sunset. They also need a blender to make blended drinks! The staff is amazing. They are polite, professional, friendly, and eager to make your stay as comfortable as possible. From the concierge, valet, kitchen staff, and cleaning crew to the bartender and spa staff. They truly make your stay top notch. The rooms are beautiful and spacious. The resort is very close to the ocean, though the photos are a bit misleading since they make it look like you just go out the door onto the beach. It’s about a mile walk to get there. The massage therapist was amazing. They bring everything to your room and tailor the massage to your preferences. The deep tissue massage was exactly what I needed. I would definitely stay again!

Reviewed on 6 Jul. 2025

Level Los Angeles Downtown - South Olive

Level Los Angeles Downtown - South Olive

4.5 out of 5
Downtown Los Angeles
per person
17 Oct - 24 Oct
found 1 day ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
8.4/10 Very Good! (1,132 reviews)
I loved everything about it!

Reviewed on 4 Aug. 2025

Winchester Holiday

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 Wiens Cellars

Our pick of the best Winchester Hotel Deals

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
8.6/10 Excellent! (3,689 reviews)
Wagyu Excellent
"Loved the pool, bar at the pool and food. Only thing I suggest is to have a small area for kids and the rest for adults. Wagyu Burgers were excellent. Noodle restaurant was excellent. the bars were EXCELLENT. had a great experience! thank you"

Reviewed on 5 Aug. 2025

Get rates
Pala Casino Spa And Resort
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 AU$360 per night from 6 Aug to 7 Aug
AU$360
6 Aug - 7 Aug
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
"Absolutely amazing. Beautiful all the way around. Staff was so helpful. So excited to come back and visit"

Reviewed on 3 Aug. 2025

South Coast Winery Resort and Spa
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! (591 reviews)
"Pala was under construction however our stay was still great! The exterior might not be pristine but the rooms were super nice and clean! Very spacious!"

Reviewed on 1 Aug. 2025

Get rates
Pala Mesa Golf Resort
See all 1,507 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices from AU$1,892 on Expedia for your Winchester getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
February, September and December are the best times to search for cheap Winchester holiday packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodation.
How many days is enough for Winchester?
With a well-organised itinerary, you can easily tick off the main Winchester sights in a few days. But if you prefer to discover lesser-known spots or take day trips, consider booking your Winchester holiday for longer.
How to find the best Winchester package deals?
Use Expedia's handy filters to help you find some of the best Winchester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Winchester package deals in the off-season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you great savings when compared to arranging stays and flights separately. Better still, you can customise your Winchester getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a holiday package to Winchester?
Enjoy amazing discounts by reserving your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for a spur-of-the-moment Winchester trip.
How to plan a trip to Winchester?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to go to Winchester.
  2. Budget wisely: Besides the cost of your hotel, you'll need to factor in other expenses too. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Winchester.
  3. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Winchester. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your accommodation and airfare: Once you've settled on your travel dates and duration, lock in the right Winchester holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.