Winterland Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Winterland

Jag Boutique Hotel

Jag Boutique Hotel

4.5 out of 5
115 George Street West, St. John's, NL
9.4/10 Exceptional! (1,655 reviews)
"Very convenient and I like it’s artistic decoration"

Reviewed on 24 Aug 2025

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Jag Boutique Hotel
Sandman Signature St. John's Hotel

Sandman Signature St. John's Hotel

3.5 out of 5
227 Kenmount Road, St. John's, NL
Fully refundableReserve now, pay when you stay
The price is 3.009.157 ₫ per night from 28 Sept to 29 Sept
3.009.157 ₫
3.642.997 ₫ total
28 Sept - 29 Sept
includes taxes & fees
8.8/10 Excellent! (2,113 reviews)
"It was a clean and well maintained Hotel."

Reviewed on 22 Aug 2025

Sandman Signature St. John's Hotel
Best Western Plus St. John's Airport Hotel and Suites

Best Western Plus St. John's Airport Hotel and Suites

4 out of 5
34 Jetstream Avenue, St. John's, NL
Fully refundableReserve now, pay when you stay
The price is 3.087.932 ₫ per night from 31 Aug to 1 Sept
3.087.932 ₫
3.693.167 ₫ total
31 Aug - 1 Sept
includes taxes & fees
Best Western Plus St. John's Airport Hotel and Suites
See all 853 properties in Newfoundland and Labrador
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 holiday package cost?
You can pick up a holiday package to this destination on Expedia. But how much your holiday 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?
If you're hoping to book a cheap Winterland holiday package, consider planning a trip in January, February and November. You'll typically find lower rates on accommodation and flights during these quieter months — ideal for travellers wishing to save money.
How many days is enough for Winterland?
With a well-planned schedule, you can easily hit the main Winterland sights in a handful of days. But if you'd like to discover lesser-known spots or take day trips, think about booking your Winterland holiday 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 holiday as a package?
You can enjoy significant savings on your Winterland retreat by booking a customised holiday 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 holiday 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.
How to plan a trip to Winterland?

  1. Pick your dates: What you plan to do in Winterland and your favourite season can help you decide when to travel.
  2. Set your budget: Consider expenses such as flights, food and transportation when calculating how much to put aside for your trip to Winterland. Then, choose a property that fits your budget, whether that's a wallet-friendly stay or a deluxe retreat.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you'd like to experience in Winterland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to pick a Winterland holiday package that brings all your bookings together.