Winterland Vacations from $363

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The Latest Winterland vacation packages

Price found within the past 48 hours. Click for updated prices.
Westgate Las Vegas Resort & Casino

Westgate Las Vegas Resort & Casino

4 out of 5
Price was $988, price is now $363 per person
$363
per person
Mar 21 - Mar 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Las Vegas (LAS)
8/10 Very Good! (5,163 reviews)
Front desk staff was awesome and the place awesome but there were to many staff members trying to get you to buy timeshare.We were bombarded with sells people every time you walked down the hall. Also to many people in the stores trying to pull you into their store selling crap!

Reviewed on Jan 18, 2026

Hotel Alameda Highline

Hotel Alameda Highline

4.5 out of 5
Manhattan
Price was $3,303, price is now $622 per person
$622
per person
Mar 11 - Mar 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to New York (JFK)
7.6/10 Good! (793 reviews)
No frills but good location and meets all the needs.

Reviewed on Jan 4, 2026

Miami Downtown Condos

Miami Downtown Condos

5 out of 5
Downtown Miami
Price was $2,879, price is now $967 per person
$967
per person
Mar 26 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (72 reviews)
The room wasn’t cleaned when we arrived about 30 minutes after the check in time. It took about 2 hours to finally have the room cleaned and ready. I wished a smooth check in process and parking information before arriving.

Reviewed on Jan 8, 2026

Creekside Inn

Creekside Inn

2.5 out of 5
Price was $1,207, price is now $487 per person
$487
per person
Mar 30 - Apr 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
Excelente personal muy amable

Reviewed on Jan 16, 2026

Westgate Flamingo Bay Resort

Westgate Flamingo Bay Resort

4 out of 5
Spring Valley
Price was $1,528, price is now $654 per person
$654
per person
Mar 4 - Mar 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Las Vegas (LAS)
8.8/10 Excellent! (1,000 reviews)
Fireplace was lit and what I mean is “ it was awesome”

Reviewed on Jan 16, 2026

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Winterland Hotel Deals

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 NL
9/10 Wonderful! (2 reviews)
Delightful

Reviewed on Sep 14, 2025

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Take it easy at this tranquil 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! (3 reviews)
We were home for a funeral and this property was perfect for us to all stay together. Beautiful home

Reviewed on Oct 10, 2025

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Escape to your private oasis in our ocean front home with breathtaking views.
Home On The Pond

Home On The Pond

Grand Bank NL
10/10 Exceptional! (10 reviews)
Nice size space, open concept

Reviewed on Sep 8, 2025

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Home On The Pond
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.

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 $363 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.