Winterland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Winterland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Price was CA $1,178, price is now CA $558 per person
CA $558
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
8.8/10 Excellent! (1,007 reviews)
Realice mi reservación, llegué al hotel y nunca apareció mi reservación en el sistema del hotel. Me comuniqué con expedía y ellos me indicaron que todo estaba bien, pero el hotel nunca me dio solución. Espere al rededor de 1 hora y media mi grupo y yo. Por más que les dije que tenía factura de pago, reservación y confirmación no fue posible que me dejaran ingresar a descansar.

Reviewed on Jul 18, 2026

Encore Inn Inglewood

Encore Inn Inglewood

2.5 out of 5
Lockhaven
Price was CA $2,279, price is now CA $892 per person
CA $892
per person
Aug 30 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Los Angeles (LAX)
6.4/10 (173 reviews)
Walked in the room and walked out Room had roaches and mice walking around Blanket looked dirty The room had an awful smell The worker offer another room but it was the same The picture on the website showed a nice looking place but once you see it real bad

Reviewed on Jul 13, 2026

Hollywood Inn Suites Hotel

Hollywood Inn Suites Hotel

2.5 out of 5
Price was CA $1,775, price is now CA $896 per person
CA $896
per person
Sep 29 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Los Angeles (LAX)
8.4/10 Very good! (1,945 reviews)

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
South of Wilshire
Price was CA $1,127, price is now CA $577 per person
CA $577
per person
Sep 27 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Los Angeles (LAX)
8.2/10 Very good! (1,006 reviews)

Virgin Hotel Las Vegas, Curio Collection by Hilton

Virgin Hotel Las Vegas, Curio Collection by Hilton

4.5 out of 5
Price was CA $1,206, price is now CA $630 per person
CA $630
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Las Vegas (LAS)
9/10 Wonderful! (8,400 reviews)

Ready to book your vacation to Winterland?

 

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Winterland Hotel Deals

Cozy home with a view of the ocean !

Cozy home with a view of the ocean !

Grand Bank NL
The price is CA $200 per night from Aug 5 to Aug 6
CA $200
CA $262 total
Aug 5 - Aug 6
includes taxes & fees
10/10 Exceptional! (6 reviews)
"Ideal for couples travelling together or singles that don't share rooms."

Reviewed on Jul 20, 2026

Cozy home with a view of the ocean !
Ocean view! Relax at this peaceful getaway only steps from the beach!

Ocean view! Relax at this peaceful getaway only steps from the beach!

Grand Beach NL
9/10 Wonderful! (6 reviews)
"It’s a lovely place"

Reviewed on Jun 12, 2026

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Ocean view! Relax at this peaceful getaway only steps from the beach!
Escape to your private oasis in our ocean front home with breathtaking views.

Escape to your private oasis in our ocean front home with breathtaking views.

Grand Bank NL
10/10 Exceptional! (9 reviews)
"Very clean."

Reviewed on Jul 15, 2026

Get rates
Escape to your private oasis in our ocean front home with breathtaking views.
See all 10 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winterland vacation package cost?
You can snap up a vacation package to this top destination from CA $558 on Expedia. But how much your vacation to Winterland costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Winterland?
You're likely to find lower rates and better availability in January, February and November. Check out our cheap Winterland vacation packages and you could score some great off-season deals.
How many days is enough for Winterland?
With a well-planned itinerary, you can easily tick off the main Winterland attractions in a few days. But if you prefer to venture off the beaten track or go on day trips, think about booking your Winterland vacation for longer.
How to find the best Winterland package deals?
Use Expedia's filters to help you find some unbeatable Winterland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Winterland package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winterland vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component individually. And you'll still get the freedom to create a tailored Winterland vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Winterland?
Enjoy amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winterland break.
How to plan a trip to Winterland?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to visit Winterland.
  2. Work out your budget: Ensure you have enough money to pay for everything from transportation and food to flights and activities. Your accommodations will likely be the biggest expense during your trip to Winterland.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to get to in Winterland. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your accommodations and airfare: After you've nailed down your travel dates and duration, lock in the perfect Winterland 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.