Winchester Holidays from AU$1,573

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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.
ERTH INN by AGA Los Angeles

ERTH INN by AGA Los Angeles

3 out of 5
per person
1 Nov - 6 Nov
found 5 hours ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
7.6/10 Good! (1,000 reviews)
Came for a procedure at USC & hotel is conveniently located across the street.

Reviewed on 6 Aug. 2025

DoubleTree by Hilton Carson

DoubleTree by Hilton Carson

4 out of 5
per person
23 Oct - 30 Oct
found 1 day ago
Return direct flight included
Melbourne (MEL) to Los Angeles (LAX)
8.4/10 Very Good! (1,001 reviews)
We stayed for a week. We had Devean at the desk help us and he made sure we had enough towels and that our tv was working as it was not at the beginning. He did great! Very professional.

Reviewed on 9 Aug. 2025

Budget Inn Hollywood

Budget Inn Hollywood

2 out of 5
Hollywood
per person
1 Nov - 6 Nov
found 5 hours ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
5.2/10 (234 reviews)
The staff was amazing. On top of their game. Very helpful. All the bad reviews. Its hollywood. Full of life. Full of character. We were super happy. Thanks guys.

Reviewed on 29 Jul. 2025

Welcome Inn on Colorado Blvd

Welcome Inn on Colorado Blvd

2 out of 5
Eagle Rock
per person
1 Nov - 6 Nov
found 5 hours ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
7.4/10 Good! (1,001 reviews)
The room next to me had the TV on until midnight and back on at 4 am. I could hear them talking through the walls also at 4am. They wouldn’t let me cancel my second night but I left anyway. You get what you pay for so I accept that.

Reviewed on 4 Aug. 2025

Urban Chic Apart-Hotels in Central LA

Urban Chic Apart-Hotels in Central LA

2 out of 5
Mid City
per person
1 Nov - 7 Nov
found 7 hours ago
Return direct flight included
Brisbane (BNE) to Los Angeles (LAX)
No reviews

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! (3,699 reviews)
"Room was big, clean, and casino was awesome! Food was great tooo!!!"

Reviewed on 7 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$369 per night from 18 Aug to 19 Aug
AU$369
18 Aug - 19 Aug
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"Quiet"

Reviewed on 9 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! (610 reviews)
"Hotel restaurant food was great. Beds were comfortable and temperature/ AC inside hotel rooms worked well. Rooms are in separate buildings far away from the lobby, and are not easily walkable with the construction. Pool was closed."

Reviewed on 9 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$1,573 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.