Sterling Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 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
Your Sterling Vacation
When you choose a Sterling vacation package, you can kick back and enjoy your getaway to the fullest. Delve into the sights and sounds of this fascinating city knowing that all your travel arrangements have been taken care of before you go. Make your trip to Sterling even more fun by including some sightseeing. Claws N Paws Wild Animal Park, Brooks Lake and Wood Winery are among the big attractions worth exploring. Expedia is here to help you escape your routine. Tailor your vacation to Sterling to suit your style of travel, whatever that may be!
Top Sterling vacation deals
- The St. Regis New York
Jan 15 - Jan 17The St. Regis New York + Flight
Manhattan2 nights5.0 star property9.2/10 - Wonderful (295 reviews)"The managers need complete retraining or higher managers that are way more capable in dealing with customers and not fighting and arguing with them and telling them they’re wrong"Reviewed November 6, 2026Roundtrip • Toronto (YTO) - New York (JFK)YYZ - LGA • Nonstop LGA - YYZ • NonstopCA $2,487CA $1,337found 2 days agoper traveller - JW Marriott Essex House New York
Jan 8 - Jan 11JW Marriott Essex House New York + Flight
Manhattan3 nights4.5 star property8.8/10 - Excellent (1,000 reviews)Roundtrip • Toronto (YTO) - New York (JFK)YYZ - LGA • Nonstop LGA - YYZ • NonstopCA $2,503CA $1,382found 1 day agoper traveller - Eurostars The Chemists’ Club Hotel
Jan 10 - Jan 15Eurostars The Chemists’ Club Hotel + Flight
Manhattan5 nights4.0 star property9.4/10 - Exceptional (565 reviews)Roundtrip • Montreal (YUL) - New York (JFK)YUL - LGA • 1 stop LGA - YUL • 1 stopCA $2,739CA $1,621found 2 days agoper traveller - 1 Hotel Brooklyn Bridge
Dec 16 - Dec 201 Hotel Brooklyn Bridge + Flight
Brooklyn4 nights5.0 star property9.2/10 - Wonderful (1,001 reviews)Roundtrip • Toronto (YTO) - New York (JFK)YYZ - EWR • Nonstop LGA - YYZ • NonstopCA $4,809CA $3,010found 2 days agoper traveller - The Langham, New York, Fifth Avenue
Jan 10 - Jan 15The Langham, New York, Fifth Avenue + Flight
Manhattan5 nights5.0 star property9.6/10 - Exceptional (1,000 reviews)Roundtrip • Montreal (YUL) - New York (JFK)YUL - LGA • 1 stop LGA - YUL • 1 stopCA $4,525CA $2,896found 2 days agoper traveller
Frequently Asked Questions
How much does a Sterling vacation package cost?
You'll find cheap prices from CA $1,337 on Expedia for your Sterling break. However, a range of factors like the hotel choice, length of stay and season will influence how much your vacation to Sterling costs.
What are the cheapest months to go to Sterling?
January, February and March are great times to search for cheap Sterling vacation packages. Travelling in quieter periods means you can generally find better prices on flights and accommodations.
How many days is enough for Sterling?
Generally, a few days is enough for a Sterling vacation. With a well-organized schedule, you can see all the best attractions like Wood Winery, as well as discover some hidden treasures along the way.
How to find the best Sterling package deals?
Landing a cheap Sterling package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most pocket-friendly Sterling package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Sterling vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component individually. And you'll still get the freedom to create a customized Sterling vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Sterling?
If you have your Sterling vacation dates finalized, book early to bag some incredible deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Sterling?
- Pick the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Sterling.
- Plan your budget wisely: As well as the cost of your hotel, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside some extra funds for unexpected expenses that may crop up during your trip to Sterling.
- Decide how long to go for: Now that you know more about Sterling, you can work out the ideal length of your vacation. Put together a rough itinerary and allocate enough time to cover everything you want to do.
- Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find a Sterling vacation package that brings all your bookings together.