Winterland Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Winterland Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Glendale Hotel

Glendale Hotel

2.5 out of 5
Somerset
Save 100% on your flight
Price was S$621, price is now S$393 per person
S$393
per person
26 Sept - 29 Sept
found 3 hours ago
Return flight included
Orlando (MCO) to Los Angeles (LAX)
8.4/10 Very Good! (2,680 reviews)
Loved the jacuzzi/tub. Easy check in. Clean.

Reviewed on 22 Aug, 2025

The LEEF Hotel

The LEEF Hotel

2 out of 5
Citrus Grove
Save 100% on your flight
Price was S$779, price is now S$413 per person
S$413
per person
26 Sept - 29 Sept
found 3 hours ago
Return flight included
Orlando (MCO) to Los Angeles (LAX)
8.6/10 Excellent! (150 reviews)
Everything was super clean and easy to check in. The area is decent and I felt safe. I parked my car outside the hotel & was not worried about it at all. Only problem we had was our room door not opening on our 2nd night but other than that everything was good.

Reviewed on 23 Aug, 2025

SIRTAJ - Beverly Hills

SIRTAJ - Beverly Hills

4 out of 5
Save 100% on your flight
Price was S$1,010, price is now S$567 per person
S$567
per person
26 Sept - 29 Sept
found 3 hours ago
Return flight included
Orlando (MCO) to Los Angeles (LAX)
8.4/10 Very Good! (1,005 reviews)
It’s very shabby dark gloomy and not well maintained

Reviewed on 20 Aug, 2025

Fairmont Century Plaza Gold Experience

Fairmont Century Plaza Gold Experience

5 out of 5
Century City
Save 100% on your flight
Price was S$1,836, price is now S$1,235 per person
S$1,235
per person
26 Sept - 29 Sept
found 3 hours ago
Return flight included
Orlando (MCO) to Los Angeles (LAX)
9.8/10 Exceptional! (117 reviews)
Alice and the staff in the Gold Experience were beyond helpful. Loved the room, balcony and service overall.

Reviewed on 11 Aug, 2025

Fairmont Century Plaza

Fairmont Century Plaza

5 out of 5
Century City
Save 100% on your flight
Price was S$1,594, price is now S$1,083 per person
S$1,083
per person
26 Sept - 29 Sept
found 3 hours ago
Return flight included
Orlando (MCO) to Los Angeles (LAX)
9.2/10 Wonderful! (464 reviews)
Our stay was very nice. There is a lot of construction going on but the hotel was very nice. I was there to take my granddaughter to the American Girl store. It was an easy walk and the Century City mall was perfect.

Reviewed on 20 Aug, 2025

Top hotels in Winterland

Jag Boutique Hotel

Jag Boutique Hotel

4.5 out of 5
115 George Street West, St. John's, NL
Fully refundableReserve now, pay when you stay
9.4/10 Exceptional! (1,646 reviews)
"This is a really fun hotel, and the lavish rooms were amazing! The staff, especially the concierge at the door were truly wonderful- chatty and friendly, with great & helpful recommendations. We did valet parking which was great, but means I can’t speak to the ease of self parking. The location is ..."

Reviewed on 21 Aug, 2025

Get rates
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 S$186 per night from 21 Sept to 22 Sept
S$186
21 Sept - 22 Sept
includes taxes & fees
8.8/10 Excellent! (2,105 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 S$199 per night from 31 Aug to 1 Sept
S$199
31 Aug - 1 Sept
includes taxes & fees
9/10 Wonderful! (1,190 reviews)
"Overall great. But could hear the people above me more than I liked."

Reviewed on 22 Aug, 2025

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 from S$393 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.

* 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.