Winterland Vacations from $484
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The Latest Winterland vacation packages
Price found within the past 48 hours. Click for updated prices.
Harrah’s Las Vegas – A Caesars Rewards Destination
Las Vegas Strip
$512
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Dallas (DAL) to Las Vegas (LAS)
8.2/10 Very Good! (16,422 reviews)
I really enjoyed the location of the property. The valet parking was great. The hotel staff was very prompt and I was at the door early check-in, which made me very excited. They allow me to check in at 10 AM because I arrived early. The food at the property was very good and centrally located to everything in the middle of the strip and it was a great experience. Look forward to seeing you again. My executive suite was very large and accommodating.
Reviewed on Sep 1, 2026
UPSUN HOTEL
South Beach
$652
per person
Nov 6 - Nov 13
found 1 day ago
Roundtrip flight included
San Juan (SJU) to Miami (MIA)
8.8/10 Excellent! (764 reviews)
Beautiful hotel with one of the area's most popular breakfast spots. Make sure you stop for a coffee or take it up to the rooftop. Be aware that the beach options they provide are not close, but they are worth the trip. Parking was ideal in the area or in the garage. Staff was amazing. Rooms could be a bit more fully furnished given the amount of space, but overall very comfortable, plus the balcony is a convenient add-on when you need a breath of fresh air.
Reviewed on Aug 24, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
$6,105
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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
Winterland Hotel Deals
Ocean view! Relax at this peaceful getaway only steps from the beach!
Grand Beach NL
9.4/10 Exceptional! (9 reviews)
"Lieu idéal pour prendre du repos, endroit plus que calme, on déguste le silence. Tout ce qu’il manque serait un lit Queen plutôt que double sinon tout est parfait!"
Reviewed on Aug 12, 2026
Cozy home with a view of the ocean !
Grand Bank NL
$165 nightly
$189 total
Sep 8 - Sep 9
Total with taxes and fees
10/10 Exceptional! (15 reviews)
"This is a beautiful 2 bedroom house. Very clean and modern. Lots of Keurig coffee pods.Beds are comfortable. It is about an 8 minute drive to the ferry terminal for St. Pierre and Miquelon. The owner was available through the VRBO app for questions. I would definitely stay here again."
Reviewed on Aug 11, 2026
Escape to your private oasis in our ocean front home with breathtaking views.
Grand Bank NL
10/10 Exceptional! (12 reviews)
"Beautiful house and location! So clean! One guest left their phone and it was so easy to get back!"
Reviewed on Aug 26, 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.
Find the Best Winterland Vacation Packages
Winterland Essential Information
Language | English |
|---|---|
Currency | Canadian dollars |
Top Sights | Marystown Heritage Museum, Burin Heritage Museums and Frenchmans Cove Provincial Park |
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Frequently asked questions
How much does a Winterland vacation package cost?
You can pick up a vacation package to this destination from $484 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?
November, December and January are the best times to look for cheap Winterland vacation packages. Opting to travel in less busy periods means you can typically find lower prices on hotels and flights.
How many days is enough for Winterland?
With a well-planned itinerary, you can easily hit the main Winterland sights in a few days. But if you prefer to discover lesser-known spots or go on 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.
Does Expedia offer Book Now, Pay Later Winterland vacation packages?
Your Winterland break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
