Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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.
Northwood Inn Prairie Du Chien

Northwood Inn Prairie Du Chien

2 out of 5
Southside
per person
Sep 15 - Sep 20
found 21 hours ago
Roundtrip flight included
Vancouver (YVR) to La Crosse (LSE)
8.4/10 Very Good! (46 reviews)
Very nice. Great location. Ended up changing room with no probems.

Reviewed on Jul. 26, 2025

Hatchery Riverside Hotel & Event Venue

Hatchery Riverside Hotel & Event Venue

3 out of 5
Historic Downtown La Crosse
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to La Crosse (LSE)
10/10 Exceptional! (57 reviews)
This hotel was so beautiful, comfortable and quiet.

Reviewed on Aug. 4, 2025

AmericInn by Wyndham Viroqua

AmericInn by Wyndham Viroqua

2.5 out of 5
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to La Crosse (LSE)
8.2/10 Very Good! (299 reviews)
Big room roll in shower really helped me to access the shower with ease.Helpful friendly staff top marks

Reviewed on Jul. 17, 2025

AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

2.5 out of 5
Northside
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to La Crosse (LSE)
7.6/10 Good! (1,001 reviews)
No grab bars in the bathrooms. VERY cheep toilet paper. No inside restaurant. I’m sure the towels were clean, but they were very thin, stained, scratchy, and appeared to be very old. For the price, I didn’t think the hotel lived up up the Whyndham name.

Reviewed on Aug. 4, 2025

Gundersen Hotel & Suites

Gundersen Hotel & Suites

2.5 out of 5
Powell-Poage-Hamilton
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to La Crosse (LSE)
9.4/10 Exceptional! (1,000 reviews)
Bed was great, the pillows not so much. Close to downtown. Nice, clean place!

Reviewed on Aug. 6, 2025

Ready to book your vacation to Portland?

 

Choose your dates

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 $144 per night from Sep 1 to Sep 2
CA $144
CA $163 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (1,568 reviews)
"short overnighter everything was good, except didn't h a ve coffee at breakfast"

Reviewed on Aug. 4, 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 CA $83 per night from Sep 7 to Sep 8
CA $83
CA $96 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (1,007 reviews)
".."

Reviewed on Aug. 3, 2025

Baymont by Wyndham La Crosse/Onalaska
Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

Holiday Inn Express & Suites Onalaska La Crosse Area by IHG

2.5 out of 5
2614 MIDWEST DRIVE, Onalaska, WI
Fully refundable
The price is CA $163 per night from Aug 10 to Aug 11
CA $163
CA $184 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (447 reviews)
"We had a great stay! The hotel is new and clean. The staff are so welcoming and friendly. Our room was perfect and the beds were comfortable. The only trouble we had was that the bathroom door latch wasn’t aligned properly so the door could not be fully shut. But otherwise the rest of the stay was ..."

Reviewed on Aug. 3, 2025

Holiday Inn Express & Suites Onalaska La Crosse Area by IHG
See all 236 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Portland vacation package cost?
Offering great value package deals from CA $504 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.

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