Portland Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    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

Top hotels in Portland

Holiday Inn Express & Suites Portland by IHG
Holiday Inn Express & Suites Portland by IHG
2.5 out of 5
100 Holiday Dr, Portland, IN
Fully refundable
The price is S$149 per night from 13 Jul to 14 Jul
S$149
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (327 reviews)
"Went to eldora for the dream and was close to track to get cleaned up and get some well needed rest."

Reviewed on 9 Jun, 2025

Holiday Inn Express & Suites Portland by IHG
Motel 6 Portland, IN
Motel 6 Portland, IN
2 out of 5
1147 US-27, Portland, IN
Fully refundableReserve now, pay when you stay
The price is S$107 per night from 28 Jun to 29 Jun
S$107
28 Jun - 29 Jun
includes taxes & fees
6.6/10 (64 reviews)
"Staff had to be called no one to greet me to chk in..."

Reviewed on 11 Jun, 2025

Motel 6 Portland, IN
Hoosier Inn
Hoosier Inn
2.5 out of 5
1620 N Meridian St, Portland, IN
Fully refundable
The price is S$112 per night from 4 Jul to 5 Jul
S$112
4 Jul - 5 Jul
includes taxes & fees
8.8/10 Excellent! (122 reviews)
"Air conditioner ..couldn’t find happy medium. Room was either cold or warm. Otherwise it was fine."

Reviewed on 22 Jun, 2025

Hoosier Inn
See all 120 properties in Portland
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 Portland holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Portland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
If you'd like to book a cheap Portland holiday package, consider planning a trip in January, February and March. You're likely to find better prices on hotels and airfares during these quieter months --- perfect for travellers wishing to save money.
How many days is enough for Portland?
Typically, a handful of days is enough to tick off the top sights during your Portland holiday. However, if you want to have time to unwind or go on day trips, consider extending your itinerary.
How to find the best Portland package deals?
Use Expedia's filters to help you find some terrific Portland package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or search for Portland package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to book your holiday package as soon as possible.
Is it cheaper to book a Portland holiday as a package?
An Expedia holiday package could land you significant savings when compared to arranging flights and stays individually. Better still, you can tailor your Portland trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Browse our bundle deals and find out how much you can save.
When to book a holiday package to Portland?
If you have your Portland travel dates finalized, book as soon as you can to score some unbeatable deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spontaneous trips? Our last-minute deals are great for quick escapes.
How to plan a trip to Portland?

  1. Choose when to go: Check your schedule and get packing. Your preferred time of year and the activities available will also help you decide when to escape to Portland.
  2. Plan your budget wisely: As well as the cost of your stay, you'll need to consider other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected costs that may come up during your trip to Portland.
  3. Decide how long to go for: Now that you know more about Portland, you can work out the right length of your break. Put together a draft plan and give yourself enough time to cover everything you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to choose a Portland 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.