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.
The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Price was CA $1,121, price is now CA $594 per person
CA $594
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.6/10 Excellent! (150 reviews)
Everything was super clean and easy to check in. The area is decent and I felt safe. I parked my car outside the hotel & was not worried about it at all. Only problem we had was our room door not opening on our 2nd night but other than that everything was good.

Reviewed on Aug. 23, 2025

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

Los Angeles Deluxe Suites - 2 Bedrooms & 2 Bathrooms

4.5 out of 5
Hollywood
Price was CA $1,762, price is now CA $822 per person
CA $822
per person
Oct 16 - Oct 20
found 24 hours ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
9.2/10 Wonderful! (73 reviews)
Beds were good altough the bed covers were stained everything else was good.

Reviewed on Jul. 31, 2025

The Cole

The Cole

3.5 out of 5
Little Tuscany
Price was CA $1,545, price is now CA $831 per person
CA $831
per person
Oct 9 - Oct 15
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Los Angeles (LAX)
8.4/10 Very Good! (293 reviews)
For the price of the rooms this hotel hit the spot. Good location, clean, and easy check in/out process.

Reviewed on Aug. 11, 2025

Hyatt Vacation Club at The Welk, San Diego Area

Hyatt Vacation Club at The Welk, San Diego Area

3.5 out of 5
Lawrence Welk Resort Village
Price was CA $1,510, price is now CA $821 per person
CA $821
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to San Diego (SAN)
8.2/10 Very Good! (1,385 reviews)
Fam and golfers resort

Reviewed on Aug. 27, 2025

Quintessence ApartHotel

Quintessence ApartHotel

2 out of 5
Hollywood
Price was CA $1,583, price is now CA $878 per person
CA $878
per person
Oct 10 - Oct 15
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.8/10 Excellent! (64 reviews)
The apartment was really clean. There are many shops and restaurants as well as walking distance to the walk of fame. We didn’t like that we could hear people walking above us at all hours, but this is no fault of the owner. The place itself was excellent and we would stay there again.

Reviewed on Aug. 20, 2025

Ready to book your vacation to Winchester?

 

Choose your dates

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 $185 per night from Sep 18 to Sep 19
CA $185
CA $228 total
Sep 18 - Sep 19
includes taxes & fees
8.6/10 Excellent! (3,779 reviews)
"Property is smaller than Pechanga, and easier to traverse. Bathrooms are maintained continuously."

Reviewed on Aug. 24, 2025

Pala Casino Spa And Resort
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 CA $119 per night from Sep 2 to Sep 3
CA $119
CA $145 total
Sep 2 - Sep 3
includes taxes & fees
8.8/10 Excellent! (636 reviews)
"Front desk was amazing. She got me out of the lobby pretty fast and got Me Into a room with a view"

Reviewed on Aug. 24, 2025

Pala Mesa Golf 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 $285 per night from Sep 1 to Sep 2
CA $285
CA $373 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"I love opening the French doors right to the vineyards. So peaceful. And the pool area with poolside food and drink service with subtle spa music in the background is so relaxing"

Reviewed on Aug. 21, 2025

South Coast Winery Resort and Spa
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
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Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this destination from CA $594 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.