Winchester Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    Find the right fit

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

    Plan, book, and manage your trip all in one place

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 ฿5,839 per night from 15 Jul to 16 Jul
฿5,839
฿6,955 total
15 Jul - 16 Jul
includes taxes & fees
8.6/10 Excellent! (3,523 reviews)
"It's a casino property. At least they have security monitoring people before they get on the elevators to ensure you are a guest."

Reviewed on 9 Jul 2025

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 ฿11,322 per night from 1 Aug to 2 Aug
฿11,322
฿13,806 total
1 Aug - 2 Aug
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"Inasmuch as I would have love to have given an excellent rating, I had to deduct a star. Upon our arrival at our cottage, the room smelled like hemp. Even the kids commented that the room smelled weird. I had to turn on the fan and AC to get rid of the smell. The control for the fan speed was missing ..."

Reviewed on 9 Jul 2025

South Coast Winery Resort and Spa
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 ฿2,307 per night from 14 Jul to 15 Jul
฿2,307
฿2,583 total
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (1,480 reviews)
"GREAT CUSTOMER SERVICE FROM YOUR FRONT DESK STAFF. WOULD RECOMMEND THIS LOCATION TO ANYONE TRAVELING TO THE TEMECULA AREA."

Reviewed on 10 Jul 2025

Signature Temecula
See all 1,505 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.

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices 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.