Winterland Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 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
Winterland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Crane's Beach House Boutique Hotel & Luxury Villas
S$8,429
per person
25 Oct - 29 Oct
found 1 day ago
Return flight included
Singapore (SIN) to Miami (MIA)
9.6/10 Exceptional! (1,024 reviews)
The property is a hidden gem. It was a great experience from check-in to check out. The staff was incredibly helpful and the housekeepers who were probably the best I’ve ever had at any hotel. The room was very clean and modern. The only suggestion I could make is that the beds would be a little softer.
Reviewed on 2 Sept, 2026
Top hotels in Winterland
Jag Boutique Hotel
115 George Street West St. John's NL
Fully refundableReserve now, pay when you stay
S$187
30 Sept - 1 Oct
includes taxes & fees
9.4/10 Exceptional! (2,507 reviews)
"Great place. I would stay there again"
Reviewed on 4 Sept, 2026
Holiday Inn St. John's Conference Centre by IHG
180 Portugal Cove Road St. John's NL
Fully refundable
S$172
3 Oct - 4 Oct
includes taxes & fees
8/10 Very good! (1,008 reviews)
"My kids were disappointed the pool closed at 9pm, we were school shopping and didnt get to the hotel till after that...should be open till at least 10. Two queen beds which sleeps 4 and only two each of the towels and face cloths, very inconvenient and not necessary. Should at least be 4 bath towels ..."
Reviewed on 4 Sept, 2026
Sandman Signature St. John's Hotel
227 Kenmount Road St. John's NL
Fully refundableReserve now, pay when you stay
S$171
4 Oct - 5 Oct
includes taxes & fees
8.8/10 Excellent! (2,371 reviews)
"Nice hotel, friendly staff. Very responsive to queries. Good location, close to mall, highways and restaurants. Second time we stayed . Our trip was for 11 days so we had a great feel for long term housekeeping. First rate. Parking was always available for our rental car. Overall would recommend. ..."
Reviewed on 4 Sept, 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 holiday package cost?
You can pick up a holiday package to this destination from S$1,745 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?
- Pick your dates: What you plan to do in Winterland and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
