Winterland Vacations from $957
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The Latest Winterland Vacation Packages
- Sandman Signature St. John's Hotel
Sep 22 - Sep 26Sandman Signature St. John's Hotel + Flight
Kenmount West4 nights3.5 star property8.8/10 - Excellent (2,335 reviews)"Great staff!"Reviewed July 16, 2026Roundtrip • Miami (MIA) - St. John's (YYT)MIA - YYT • 1 stop YYT - FLL • 2 stops$1,092$957found 1 day agoper traveler - Mallard Inn
Aug 15 - Aug 21Mallard Inn + Flight
Quidi Vidi6 nights3.5 star property9.8/10 - Exceptional (8 reviews)"Wistful location and a beautiful room. Very large with a nice sitting area, decorated with a spa like touch. Very comfy bed, waffle towels and bathrobe. Local toiletries to make you feel connected to the area. Conveniently located across the street from one of the best restaurants in St John’s the Mallard Cottage. An authentic experience all around with a luxury touch!"Reviewed July 1, 2026Roundtrip • Boston (BOS) - St. John's (YYT)BOS - YYT • 1 stop YYT - BOS • 1 stop$2,278$1,923found 1 day agoper traveler - Monastery Hotel
Aug 15 - Aug 21Monastery Hotel + Flight
Central6 nights5.0 star property8.8/10 - Excellent (1,005 reviews)"The building inside and outside are old and different from the photos. The interior was clean but not well maintained. The elevator was making loud noise and strange sounds both when start moving and stopping. The main light over the ceiling in our room was not working and had not been fixed. Breakfast was good and the staff who served us food at Bistro was very polite and friendly."Reviewed July 15, 2026Roundtrip • Boston (BOS) - St. John's (YYT)BOS - YYT • 1 stop YYT - BOS • 1 stop$1,336$1,152found 1 day agoper traveler - The Killick Inn & Suites
Aug 15 - Aug 21The Killick Inn & Suites + Flight
Arnold's Cove6 nights3.5 star property9.8/10 - Exceptional (152 reviews)"The unit was very clean. Accurate description and photos. Provided a stocked kitchen with everything you would need. Also the in suite laundry is great! Would definitely stay again and would recommend."Reviewed July 6, 2026Roundtrip • Boston (BOS) - St. John's (YYT)BOS - YYT • 1 stop YYT - BOS • 1 stop$1,425$1,237found 1 day agoper traveler - Ramada by Wyndham St. John's
Aug 15 - Aug 21Ramada by Wyndham St. John's + Flight
Kenmount East6 nights3.5 star property8.8/10 - Excellent (1,213 reviews)"It is a very good and neat room"Reviewed July 15, 2026Roundtrip • Boston (BOS) - St. John's (YYT)BOS - YYT • 1 stop YYT - BOS • 1 stop$1,380$1,201found 1 day agoper traveler
Frequently Asked Questions
How much does a Winterland vacation package cost?
You can pick up a vacation package to this destination from $957 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.