Winterland Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Winterland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Tahiti Village Resort & Spa
Enterprise
CA $999
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Las Vegas (LAS)
8.6/10 Excellent! (9,580 reviews)
I loved the stay I had. I would definitely stay again. I think the vibes the resort was going for really came across to us. I loved the pool and the lazy river.
Reviewed on Sep 20, 2026
SIRTAJ - Beverly Hills
South of Wilshire
CA $782
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Los Angeles (LAX)
8.2/10 Very good! (1,006 reviews)
Staff were kind and helpful. However, this is not a 4 star hotel. The beds were extremely hard, pillows went completely flat, and the elevator is very very slow.
Reviewed on Sep 19, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $16,278
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) 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
Ready to book your vacation to Winterland?
Winterland Hotel Deals
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
Escape to your private oasis in our ocean front home with breathtaking views.
Grand Bank NL
10/10 Exceptional! (13 reviews)
"Travelling from BC my 2 friends and I were on an adventure to seek out the real Newfoundland feeling and we found it at this little cottage.Right on the water, minutes walk to town and lovely interactions with locals.We were fortunate to have great weather so long walks and a grand visit to the Seaman’s ..."
Reviewed on Sep 1, 2026
Cozy home with a view of the ocean !
Grand Bank NL
CA $200
CA $262 total
Sep 21 - Sep 22
includes taxes & fees
10/10 Exceptional! (18 reviews)
"Lovely and comfortable visit. Love the decor and artwork."
Reviewed on Sep 18, 2026
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 snap up a vacation package to this top destination from CA $623 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?
- 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.
- 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.
- 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.
- 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.
