Winchester Vacations from $346

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Your Winchester Vacation

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 vacation 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 Center. Don't put off your visit to this city any longer. Your dream Winchester vacation is a couple of clicks away with Expedia.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Quiet Mind Mountain Lodge, Retreat and Spa
Malibu Country Inn
Fleur Noire Hotel - 21 and Over
Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms
Balboa Inn, On the Beach
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What to do in Winchester

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
$122 nightly
The price is $132 total per night from Dec 8 to Dec 9
$132 total
Dec 8 - Dec 9
Total with taxes and fees
8.6/10 Excellent! (4,139 reviews)
My wife and I did a mini getaway for 1 night stay for her birthday and it was amazing room really spacious. Definitely will stay again

Reviewed on Nov 28, 2025

Pala Casino Spa And Resort
Studio 6 Suites Perris, CA

Studio 6 Suites Perris, CA

2 out of 5
480 S Redlands Ave Perris CA
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Dec 7 to Dec 8
$85 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (1,021 reviews)
Yes

Reviewed on Nov 24, 2025

Studio 6 Suites Perris, CA
Hotel Xola

Hotel Xola

2.5 out of 5
24630 Sunnymead Boulevard Moreno Valley CA
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $76 total per night from Dec 4 to Dec 5
$76 total
Dec 4 - Dec 5
Total with taxes and fees
7.6/10 Good! (1,470 reviews)
Was a nice place to stay and relax

Reviewed on Nov 22, 2025

Hotel Xola
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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
San Bernardino, CA (SBD-San Bernardino Intl.)
Population
2,500
Top Sights
Wilson Creek Winery, Ponte Winery and Mulligan Family Fun Center

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Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from $346 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 vacation to Winchester costs.
What are the cheapest months to go to Winchester?
If you're looking to book a cheap Winchester vacation package, consider traveling in April, October and December. You'll generally find lower prices on accommodations and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Winchester?
Typically, a handful of days is enough to go to the major attractions during your Winchester vacation. However, if you prefer to have more time to relax or go on day trips, think about extending your itinerary.
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 vacation package as early as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging stays and flights separately. Better still, you can customize 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 vacation 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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Winchester vacation over 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.