Winterland Vacations from ￥149,458

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The Latest Winterland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
per person
Nov 5 - Nov 10
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Los Angeles (LAX)
8.4/10 Very Good! (1,002 reviews)
Clean hotel with great service. The only downsides to this property is that the $150 deposit wasn’t disclosed until after I already booked and prepaid for the room & the parking is $40 a night (in a garage that’s across the street). Other than that, this is a great place to spend a night or two.

Reviewed on Aug 9, 2025

Relais de la Poste

Relais de la Poste

3 out of 5
Rome City Centre
Save 100% on your flight
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Rome (FCO)
9.2/10 Wonderful! (549 reviews)
Everything was amazing!! The workers were so sweet and helpful and truly made our stay. The room was extremely quiet for such a busy area. Check in and check out was easy and the room comes with free espresso! We loved everything about our stay and would definitely recommend.

Reviewed on Aug 4, 2025

Albergo Etico Roma

Albergo Etico Roma

3 out of 5
Flaminio
per person
Nov 2 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Rome (FCO)
9.6/10 Exceptional! (283 reviews)
Nice room, nice hotel, pretty garden.

Reviewed on Aug 7, 2025

Fairmont Century Plaza Gold Experience

Fairmont Century Plaza Gold Experience

5 out of 5
Century City
Save 100% on your flight
per person
Oct 21 - Oct 27
found 1 hour ago
Roundtrip flight included
Tokyo (HND) to Los Angeles (LAX)
9.8/10 Exceptional! (113 reviews)
Alice and the staff in the Gold Experience were beyond helpful. Loved the room, balcony and service overall.

Reviewed on Aug 11, 2025

Hotel Riu Plaza New York Times Square

Hotel Riu Plaza New York Times Square

4 out of 5
Manhattan
Save 100% on your flight
per person
Oct 13 - Oct 20
found 8 hours ago
Roundtrip flight included
Tokyo (TYO) to New York (JFK)
9/10 Wonderful! (2,737 reviews)
Very nice property close to theaters and Times Square. Relatively easy to get to, but be sure you don’t have your cab or Uber take you to the other Riu hotel in the area like we did. Not a long walk but different location

Reviewed on Aug 10, 2025

Find the Best Winterland Vacation Packages

Winterland Hotel Deals

Home On The Pond

Home On The Pond

Grand Bank
10/10 Exceptional! (6 reviews)
"We had a great stay at"

Reviewed on Aug 8, 2025

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Home On The Pond
Fantastic ocean view! Relax at this peaceful getaway

Fantastic ocean view! Relax at this peaceful getaway

Grand Beach
10/10 Exceptional! (1 review)
"Fantastic location. Amazing view of the sunset."

Reviewed on Jul 3, 2025

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Fantastic ocean view! Relax at this peaceful getaway
Take it easy at this tranquil getaway, only steps from the beach!

Take it easy at this tranquil getaway, only steps from the beach!

Grand Beach
"My husband and I stayed here for 3 days - beautiful view, quiet and peaceful. We stopped in all the little spots on the Burin, walked the beaches, picked bake apples and hiked a trail in nearby Garnish. If you are looking for a quiet place this is the place."

Reviewed on Jul 26, 2025

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Take it easy at this tranquil getaway, only steps from the beach!
See all 7 properties in Winterland
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 Winterland vacation package cost?
You can pick up a vacation package to this destination from ￥149,458 on Expedia. But how much your vacation to Winterland costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winterland?
If you're hoping to book a cheap Winterland vacation package, consider planning a trip in January, February and November. You'll typically find lower rates on accommodations and flights during these quieter months — ideal for travelers wishing to save money.
How many days is enough for Winterland?
With a well-planned schedule, you can easily hit the main Winterland sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Winterland vacation for longer.
How to find the best Winterland package deals?
Begin your search for a Winterland package deal by entering your destination and travel dates under our "Packages" tab. Then apply some filters, like "Guest rating" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Winterland package deal right away, just change your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winterland escape off to a flying start.
Is it cheaper to book a Winterland vacation as a package?
You can enjoy significant savings on your Winterland retreat by booking a customized vacation package. Check the "Package" heading, then select your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Winterland?
If you have your Winterland travel dates confirmed, book early to score some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Winterland?

  1. Pick your dates: What you plan to do in Winterland and your favorite season can help you decide when to travel.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to Winterland. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Winterland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Winterland 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.