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 $1,513, price is now CA $582 per person
CA $582
per person
Jan 20 - Jan 24
found 2 days ago
Roundtrip flight included
Vancouver (YVR) to Las Vegas (LAS)
8.8/10 Excellent! (1,013 reviews)

Westgate Las Vegas Resort & Casino

Westgate Las Vegas Resort & Casino

4 out of 5
Price was CA $1,911, price is now CA $794 per person
CA $794
per person
Jan 20 - Jan 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Las Vegas (LAS)
8.2/10 Very good! (7,190 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was CA $45,182, price is now CA $21,708 per person
CA $21,708
per person
Jan 6 - Jan 11
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

Jet Luxury Resorts @ The Signature Condo Hotel

Jet Luxury Resorts @ The Signature Condo Hotel

4.5 out of 5
Price was CA $3,807, price is now CA $1,880 per person
CA $1,880
per person
Jan 18 - Jan 22
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Las Vegas (LAS)
8.4/10 Very good! (4,540 reviews)
Location was great. The rooms were spacious and clean.

Reviewed on Nov 3, 2026

The St. Regis New York

The St. Regis New York

5 out of 5
Manhattan
Price was CA $4,883, price is now CA $2,478 per person
CA $2,478
per person
Jan 5 - Jan 9
found 2 days ago
Roundtrip non-stop flight included
Vancouver (YVR) to New York (JFK)
9.2/10 Wonderful! (293 reviews)

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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 Nov 10 to Nov 11
CA $200
CA $251 total
Nov 10 - Nov 11
includes taxes & fees
10/10 Exceptional! (19 reviews)
"Great location and all the amenities you might need."

Reviewed on Sep 26, 2026

Cozy home with a view of the ocean !
Home On The Pond

Home On The Pond

Grand Bank NL
10/10 Exceptional! (18 reviews)
"Clean, comfortable, helpful and friendly host!"

Reviewed on Oct 31, 2026

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Home On The Pond
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! (13 reviews)
"Room clean and comfortable. Quite area. All we needed for a self touring adventure. Ferries did not work out for a trip to St Pierre Miqualon but did a couple of good coastline hikes in this area."

Reviewed on Sep 12, 2026

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Ocean view! Relax at this peaceful getaway only steps from the beach!
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 $582 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.