Portland 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
Portland Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Hilton New York Fashion District
Manhattan
S$2,171
per person
1 Oct - 4 Oct
found 1 day ago
Return direct flight included
Singapore (SIN) to New York (JFK)
9/10 Wonderful! (981 reviews)
Clean room however be prepared for it to be a tight space. Showers are very narrow and no closet in the room we had (we got the cheapest room for 1 night quick stay so it wasn’t an issue).
Reviewed on 28 Aug, 2026
Top hotels in Portland
Tay Inn
125 Dufferin Street Perth ON
Fully refundableReserve now, pay when you stay
S$113
30 Aug - 31 Aug
includes taxes & fees
9.4/10 Exceptional! (831 reviews)
"Easy access right off hwy 7. Clean and comfortable."
Reviewed on 23 Aug, 2026
Perth Parkside Hotel and Spa, BW Premier Collection
82 Peter Street Perth ON
Fully refundableReserve now, pay when you stay
S$228
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
"Excellent indoor pool"
Reviewed on 25 Aug, 2026
Econo Lodge
33 Centre Street Smiths Falls ON
Fully refundable
S$114
4 Sept - 5 Sept
includes taxes & fees
6.6/10 (987 reviews)
"Very welcoming"
Reviewed on 26 Aug, 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.
Stay near popular Portland attractions
Len's Cove Marina
Explore the waterfront in Portland with a trip to Len's Cove Marina.
Portland Beach
Why not spend a lazy afternoon at Portland Beach during your trip to Portland?
Bayview Yacht Harbour
Explore the waterfront in Portland with a trip to Bayview Yacht Harbour.
Rideau Lakes Public Library - Portland Branch
Rideau Lakes Public Library - Portland Branch is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels?
Frequently asked questions
How much does a Portland holiday package cost?
You can pick up a holiday package to this top destination from S$2,020 on Expedia. However, how much your holiday to Portland costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Portland?
To pick up cheap Portland holiday packages, organise your getaway outside of busy periods like public holidays and major events. You'll typically find better availability and lower prices when it's less busy.
How many days is enough for Portland?
Usually, a handful of days is enough to check out the main attractions during your Portland holiday. But if you'd like to have more time to rest or take day tours, consider extending your itinerary.
How to find the best Portland package deals?
Use Expedia's handy filters to find some great Portland package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Portland package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your holiday package well in advance.
Is it cheaper to book a Portland holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component individually. And you'll still get the flexibility to create a customised Portland holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Portland?
If you've got your Portland holiday dates locked in, book as early as you can to snap up some fantastic deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Portland?
- Pick the right time to travel: Your schedule, favourite season and the type of weather you like can all influence your decision on when to visit Portland.
- Plan your budget wisely: As well as the cost of your hotel, you should factor in other expenses too. These include transportation, flights and food. Also, set aside some extra funds for unexpected costs that may crop up during your trip to Portland.
- Work out your trip length: Think about how long you'd like to spend exploring Portland. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
- Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customised Portland holiday package.
* 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.
