Winchester Vacation Packages

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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.

Top Winchester Vacation 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
Save 100% on your flight
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
7.6/10 Good! (1,003 reviews)
Not very many rooms so it was quiet. Right by a hospital If there was a emergency.

Reviewed on Jun. 24, 2025

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.6/10 Excellent! (61 reviews)
The room very nice and clean !!

Reviewed on Jul. 10, 2025

Hyatt Place Glendale / Los Angeles

Hyatt Place Glendale / Los Angeles

3 out of 5
Downtown Glendale
Save 100% on your flight
per person
Aug 27 - Sep 2
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.8/10 Excellent! (1,001 reviews)
Very comfortable. Super friendly staff. Breakfast is sub par. Great location in Glendale. Would stay again.

Reviewed on Jul. 12, 2025

Hotel H-Wood

Hotel H-Wood

2.5 out of 5
Hollywood
per person
Aug 30 - Sep 6
just found
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
6/10 (509 reviews)
For the price you pay, its a bargain. The area surrounding the hotel isn't that great and limited parking on site. First come, first serve reservation. The hallways smell like piss. Probably because its easy access to thr transients in the area. However, the customer service was great. This is the place to stay if you are on a budget and only use it for sleep.

Reviewed on Jul. 10, 2025

The Velvet Rope

The Velvet Rope

3 out of 5
Uptown Design District
Save 100% on your flight
per person
Aug 13 - Aug 20
found 12 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
9.8/10 Exceptional! (61 reviews)

Ready to book your vacation to Winchester?

 

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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
The price is CA $179 per night from Aug 13 to Aug 14
CA $179
CA $221 total
Aug 13 - Aug 14
includes taxes & fees
8.6/10 Excellent! (3,544 reviews)
"Loved it alll! Only wish there were more shopping options and more dining options. They need some simple dining options not just a couple restaurants. Everything everything else was fantastic."

Reviewed on Jul. 12, 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 CA $206 per night from Aug 13 to Aug 14
CA $206
CA $278 total
Aug 13 - Aug 14
includes taxes & fees
8.8/10 Excellent! (1,007 reviews)
"It was a very clean and beautiful property . Staff was nice and friendly"

Reviewed on Jul. 13, 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 CA $87 per night from Jul 14 to Jul 15
CA $87
CA $97 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,479 reviews)
"The bedroom is large. There is no fragrant smell, which is good."

Reviewed on Jul. 8, 2025

Signature Temecula
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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this destination from CA $528 on Expedia. However, how much your vacation to Winchester costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Winchester?
If you're looking to score a cheap Winchester vacation package, consider travelling in February, September and December. You'll usually find better prices on flights and hotels during these months --- ideal for a budget-friendly break.
How many days is enough for Winchester?
Typically, a handful of days is ideal for a Winchester vacation. With a well-organized itinerary, you can check out all the leading attractions such as Western Science Centre, as well as discover some hidden gems along the way.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Winchester package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester adventure underway.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and hotels separately. Better still, you can tailor your Winchester trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a vacation package to Winchester?
If you're considering a spur-of-the-moment Winchester vacation, check out our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can find incredible deals on your flights and hotels by booking well in advance.
How to plan a trip to Winchester?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the type of activities on offer will also help you decide when to vacation in Winchester.
  2. Figure out your budget: Ensure you have enough money to pay for everything from food and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Winchester.
  3. Decide how long to go away for: Now that you know more about Winchester, you can figure out the right length of your break. Pull together a draft plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to find a Winchester vacation package that brings all your bookings together.

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