Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Portland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Comfort Inn & Suites New Lisbon

Comfort Inn & Suites New Lisbon

2.5 out of 5
Price was CA $1,219, price is now CA $1,110 per person
CA $1,110
per person
Aug 12 - Aug 19
found 3 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to La Crosse (LSE)
8.4/10 Very good! (927 reviews)
Good stay. Quite. Nice pool & whirlpool. Right next to freeway but no freeway noise.

Reviewed on Jul 2, 2026

Edge Of The Woods Motel

Edge Of The Woods Motel

2 out of 5
Price was CA $1,244, price is now CA $1,146 per person
CA $1,146
per person
Aug 12 - Aug 19
found 3 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to La Crosse (LSE)
8.8/10 Excellent! (107 reviews)
Great cheap place to stay. Bed and pillows surprisingly comfortable. Staff very welcoming. Will return!

Reviewed on Jun 22, 2026

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Portland Hotel Deals

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 CA $165 per night from Jul 23 to Jul 24
CA $165
CA $187 total
Jul 23 - Jul 24
includes taxes & fees
9/10 Wonderful! (1,530 reviews)
"Such a nice unique place to stay."

Reviewed on Jul 1, 2026

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
The price is CA $110 per night from Aug 2 to Aug 3
CA $110
CA $126 total
Aug 2 - Aug 3
includes taxes & fees
8.4/10 Very good! (1,000 reviews)
"The front desk person was out smoking when we arrived and when they came inside they were rude. There was black hair, it looked to be dog or cat hair all over the bedding and the towels in the bathroom. I went to use the fridge and their was a dessert container on the top shelf so that had not been ..."

Reviewed on Jun 30, 2026

Baymont by Wyndham La Crosse/Onalaska
AmericInn by Wyndham West Salem

AmericInn by Wyndham West Salem

3 out of 5
125 Buol Road West Salem WI
Fully refundableReserve now, pay when you stay
The price is CA $102 per night from Jul 28 to Jul 29
CA $102
CA $113 total
Jul 28 - Jul 29
includes taxes & fees
8.6/10 Excellent! (1,002 reviews)
"I chose this location for the price and the pool. The pool needs a good cleaning, but overall; I got a good deal."

Reviewed on Jul 3, 2026

AmericInn by Wyndham West Salem
See all 237 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.
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Frequently asked questions

How much does a Portland vacation package cost?
Offering great value package deals from CA $1,110 on Expedia, you'll be surprised at how little a vacation to Portland costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Portland?
If you'd like to score a cheap Portland vacation package, consider travelling in January, February and March. You'll typically find better prices on flights and accommodations during these months — perfect for budget-conscious travellers.
How many days is enough for Portland?
The ideal duration for your Portland vacation depends on what you'd like to see. Usually, a few days to a week will give you time to go to all the top attractions and discover some hidden spots along the way.
How to find the best Portland package deals?
Use Expedia's handy filters to find some tempting Portland package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Portland package deals in the off-peak season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Portland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to arranging accommodations and flights individually. Better still, you can tailor your Portland getaway to match your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Portland?
If you've got your Portland vacation dates finalized, book early to snap up some incredible deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Portland?

  1. Choose your travel dates: What you plan to do in Portland and your favourite season can help you decide when to travel.
  2. Set a budget: Consider costs such as flights, food and transportation when working out how much to set aside for your trip to Portland. Then, pick a hotel that works with your budget, whether that's a low-cost option or a high-end retreat.
  3. Work out your trip length: Think about how much time you want to spend discovering Portland. Plan your itinerary so you can get to all the experiences and attractions you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to choose a Portland vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.