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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    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

Top hotels in Portland

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
3060 S Kinney Coulee Rd, Onalaska, WI
Fully refundableReserve now, pay when you stay
The price is S$188 per night from 24 Jul to 25 Jul
S$188
24 Jul - 25 Jul
includes taxes & fees
8.8/10 Excellent! (1,556 reviews)
"This was a pleasant surprise. The woodsy, cabin vibes were great. We were treated to a drink token at the bar, which was totally unexpected. We enjoyed it very much. Rooms were nice and comfortable. Breakfast was good. it was a quick night stay so we didn't enjoy the other amenities like the pool. ..."

Reviewed on 13 Jul, 2025

Stoney Creek Hotel La Crosse - Onalaska
Baymont by Wyndham La Crosse/Onalaska

Baymont by Wyndham La Crosse/Onalaska

2.5 out of 5
3300 Kinney Coulee Rd. North, Onalaska, WI
Fully refundableReserve now, pay when you stay
The price is S$93 per night from 10 Aug to 11 Aug
S$93
10 Aug - 11 Aug
includes taxes & fees
8/10 Very Good! (1,002 reviews)
"close to everything you need. Quiet, clean room with private jacuzzi tub that ACTUALLY WORKS! Nice room and stay so far."

Reviewed on 18 Jul, 2025

Baymont by Wyndham La Crosse/Onalaska
Spark by Hilton La Crosse Onalaska

Spark by Hilton La Crosse Onalaska

2.5 out of 5
9409 Highway 16, Onalaska, WI
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 27 Jul to 28 Jul
S$125
27 Jul - 28 Jul
includes taxes & fees
Spark by Hilton La Crosse Onalaska
See all 231 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?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Portland costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Portland?
If you're looking to snag a cheap Portland holiday package, consider planning a trip in January, February and March. You'll typically find better prices on airfares and hotels during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Portland?
With a well-organised itinerary, you can easily hit the top Portland sights in a few days. But if you'd like to explore off the beaten track or take day trips, think about booking your Portland holiday for longer.
How to find the best Portland package deals?
Use Expedia's handy filters to find some of the best Portland package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Portland package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Portland holiday as a package?
You can enjoy significant savings on your Portland retreat by booking a customised holiday package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Portland?
If you have your Portland holiday dates confirmed, book as soon as you can to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Portland?

  1. Choose when to travel: Check your diary and pack your bags. Your favourite time of year and the type of activities available will also help you decide when to escape to Portland.
  2. Work out your budget: Make sure you have enough money to cover everything from meals and transportation to activities and flights. Your hotel will probably be the biggest expense during your trip to Portland.
  3. Work out your trip length: Consider how long you want to spend exploring Portland. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick 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.