Winchester Vacations from ￥165,980

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel H-Wood

Hotel H-Wood

2.5 out of 5
Hollywood
per person
Sep 2 - Sep 9
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to Los Angeles (LAX)
6/10 (509 reviews)
You get what you paid for. Definitely convenient for last minute booking for events around the area.

Reviewed on Jul 7, 2025

Regent Santa Monica Beach

Regent Santa Monica Beach

5 out of 5
Downtown Santa Monica
Save 100% on your flight
per person
Aug 27 - Aug 31
found 1 day ago
Roundtrip flight included
Tokyo (HND) to Los Angeles (LAX)
10/10 Exceptional! (8 reviews)
Raised the bar for what a great hotel and service is.

Reviewed on Jun 30, 2025

Fairmont Miramar Hotel

Fairmont Miramar Hotel

5 out of 5
Wilshire Montana
Save 100% on your flight
per person
Sep 26 - Oct 1
found 24 hours ago
Roundtrip flight included
Tokyo (TYO) to Los Angeles (LAX)
8.4/10 Very Good! (1,008 reviews)
It was a beautiful hotel with excellent amenities!

Reviewed on Jul 9, 2025

L'Ermitage Beverly Hills

L'Ermitage Beverly Hills

5 out of 5
Save 100% on your flight
per person
Sep 9 - Sep 13
found 5 hours ago
Roundtrip flight included
Tokyo (NRT) to Los Angeles (LAX)
9.6/10 Exceptional! (1,002 reviews)
Lovely rooms, location, close to the best dining & shopping areas

Reviewed on Jul 8, 2025

The Donatello

The Donatello

3.5 out of 5
Union Square
Save 100% on your flight
per person
Sep 25 - Sep 29
found 1 hour ago
Roundtrip flight included
Tokyo (NRT) to San Francisco (SFO)
9.2/10 Wonderful! (1,000 reviews)
Close to union square. Nice staff. Spacious rooms.

Reviewed on Jun 8, 2025

Find the Best Winchester Vacation Packages

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 ￥24,217 per night from Jul 15 to Jul 16
￥24,217
￥29,078 total
Jul 15 - Jul 16
includes taxes & fees
8.6/10 Excellent! (3,523 reviews)
"It's a casino property. At least they have security monitoring people before they get on the elevators to ensure you are a guest."

Reviewed on Jul 9, 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 ￥43,692 per night from Jul 18 to Jul 19
￥43,692
￥54,005 total
Jul 18 - Jul 19
includes taxes & fees
8.8/10 Excellent! (1,004 reviews)
"Room smelled a tiny bit musty, A/C controls weren't working, Keurig machine didn't work."

Reviewed on Jul 2, 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 ￥10,398 per night from Jul 14 to Jul 15
￥10,398
￥11,646 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (1,476 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.

Frequently asked questions

How much does a Winchester vacation package cost?
You'll find cheap prices from ￥165,980 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?
February, September and December are the best times to search for cheap Winchester vacation packages. Opting to travel in quieter periods means you'll typically find reduced prices on flights and accommodations.
How many days is enough for Winchester?
With a well-organized 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 vacation 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 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.
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 accommodations and airfare: Once you've settled on your travel dates and duration, lock in the right Winchester vacation package for you.

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