Winchester Holidays

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 Rp173.195 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
    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
8.6/10 Excellent! (3,434 reviews)
"The view of my room and the swimming pools ❤️❤️❤️"

Reviewed on 23 Jun 2025

Get rates
Pala Casino Spa And Resort
Motel 6 Temecula, CA - Historic Old Town
Motel 6 Temecula, CA - Historic Old Town
2 out of 5
41900 Moreno Rd, Temecula, CA
Fully refundableReserve now, pay when you stay
The price is Rp981.076 per night from 30 Jun to 1 Jul
Rp981.076
Rp1.101.258 total
30 Jun - 1 Jul
includes taxes & fees
8/10 Very Good! (1,596 reviews)
"Property and room felt clean and the staff was very friendly! A few minutes walk to Old Town Temecula. Stayed here for one night and would stay here again."

Reviewed on 23 Jun 2025

Motel 6 Temecula, CA - Historic Old Town
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
The price is Rp1.797.628 per night from 15 Jul to 16 Jul
Rp1.797.628
Rp2.137.363 total
15 Jul - 16 Jul
includes taxes & fees
8.8/10 Excellent! (518 reviews)
"I want to give a huge thank you to Mackey at Palo Mesa Golf Resort for going above and beyond to accommodate me. I had to stay at another hotel the night before and was worried about the gap between check-out and check-in, but Mackey made sure there was a smooth transition. He responded quickly and ..."

Reviewed on 23 Jun 2025

Pala Mesa Golf Resort
See all 1,514 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.