Winchester Vacations from $472

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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.
Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
Save 100% on your flight
Price was $850, price is now $472 per person
$472
per person
Mar 19 - Mar 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Los Angeles (LAX)
8.2/10 Very Good! (1,622 reviews)
Clean room, attentive staff, parki g available for a fee

Reviewed on Feb 1, 2026

The Sofia Hotel

The Sofia Hotel

3.5 out of 5
Downtown San Diego
Price was $1,261, price is now $583 per person
$583
per person
Mar 12 - Mar 17
found 1 day ago
Roundtrip flight included
Dallas (DAL) to San Diego (SAN)
8.4/10 Very Good! (1,627 reviews)
The room was very dusty. It looks like they don't do proper cleaning. Overpriced.

Reviewed on Feb 2, 2026

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
Price was $1,059, price is now $544 per person
$544
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Los Angeles (LAX)
8.4/10 Very Good! (326 reviews)
Very cute hotel. The virtual check in was a little weird at first, but pretty cool when you think about it.

Reviewed on Jan 30, 2026

The Hollywood Roosevelt

The Hollywood Roosevelt

4 out of 5
Hollywood
Save 100% on your flight
Price was $1,868, price is now $1,044 per person
$1,044
per person
Mar 7 - Mar 12
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Los Angeles (LAX)
9/10 Wonderful! (1,742 reviews)
The staff was amazing! Had an unhappy start, missing our arrival champagne & sweets, the suite wasn’t set up for us as expected… but the staff bent over backwards to make it up! Excellent service everywhere we went!

Reviewed on Feb 1, 2026

Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
Save 100% on your flight
Price was $1,050, price is now $591 per person
$591
per person
Apr 15 - Apr 22
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Los Angeles (LAX)
8.4/10 Very Good! (2,889 reviews)
Check in was seamless with a kiosk, they have a excellent coffee machine that makes espresso and add shot assortments also aflavored water machine which was also complimentary. Our room was nice, clean and updated, shower was perfect we stayed one night for a quick trip to universal studios. there is on site parking for a fee, very easy in and out, we will definitely stay here again, there is food places all around. For the price and value We were definitely pleased.

Reviewed on Feb 2, 2026

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What to do in Winchester

Sunrise Hot Air Balloon Ride in Temecula Wine Country

Morning Hot Air Balloon Ride in Temecula Wine Country

$199
per adult
92% of travellers recommend
Morning Hot Air Balloon Ride in Temecula Wine Country
Guided Temecula Winery Tour

Guided Temecula Winery Tour

$100
per adult
100% of travellers recommend
Guided Temecula Winery Tour
View the moon up close - see the lunar landing sites and and enormous craters

Temecula Wine Country Stargazing Tour

$75
per adult
Temecula Wine Country Stargazing Tour
See all activities 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
$142 nightly
The price is $153 total per night from Feb 5 to Feb 6
$153 total
Feb 5 - Feb 6
Total with taxes and fees
8.6/10 Excellent! (4,359 reviews)
Hotel was good. Rewards system sucks and no tier status goals. Spa closed and pool closed. Not told until the day before we arrived.

Reviewed on Feb 1, 2026

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
$51 nightly
The price is $57 total per night from Feb 9 to Feb 10
$57 total
Feb 9 - Feb 10
Total with taxes and fees
8.2/10 Very Good! (1,906 reviews)
Room was extremely clean. Bed was comfortable and sheets were soft. Staff was very helpful and polite. We were very impressed and will stay again!

Reviewed on Jan 31, 2026

Motel 6 Temecula, CA - Historic Old Town
Hotel Xola

Hotel Xola

2.5 out of 5
24630 Sunnymead Boulevard Moreno Valley CA
$67 nightly
The price is $76 total per night from Feb 8 to Feb 9
$76 total
Feb 8 - Feb 9
Total with taxes and fees
7.6/10 Good! (1,583 reviews)
.

Reviewed on Jan 30, 2026

Hotel Xola
See all 1,578 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.

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 $472 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.