Portland Vacations from $675

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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

The Latest Portland vacation packages

Price found within the past 48 hours. Click for updated prices.
AmericInn by Wyndham La Crosse Riverfront-Conference Center

AmericInn by Wyndham La Crosse Riverfront-Conference Center

3 out of 5
Northside
Price was $752, price is now $675 per person
$675
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
7.6/10 Good! (1,004 reviews)
Seems more run down than it used to be.

Reviewed on May 10, 2026

Hatchery Riverside Hotel & Event Venue

Hatchery Riverside Hotel & Event Venue

3 out of 5
Historic Downtown La Crosse
Price was $1,407, price is now $1,089 per person
$1,089
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
10/10 Exceptional! (92 reviews)
The Hatchery was such a great stay!! Adorable boutique hotel with stylish decor, comfortable amenities, and an overall amazing place. Super easy check in, extra perks like a Victrola in the room with vibing records paired with it, free snacks in the common area (coffee, scones, bags of chips, sodas, etc), great water pressure, and many more!!

Reviewed on Mar 8, 2026

Pearl Street Hotel & Suites

Pearl Street Hotel & Suites

2.5 out of 5
Historic Downtown La Crosse
Price was $1,346, price is now $1,182 per person
$1,182
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
8/10 Very Good! (474 reviews)
Clean and comfortable rooms

Reviewed on May 24, 2026

The Charmant Hotel

The Charmant Hotel

4 out of 5
Historic Downtown La Crosse
Price was $1,001, price is now $886 per person
$886
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
9.8/10 Exceptional! (1,004 reviews)
Everything about this property was top notch. From the hotel room to the restaurant and bar. And fabulous location!

Reviewed on May 25, 2026

Stoney Creek Hotel La Crosse - Onalaska

Stoney Creek Hotel La Crosse - Onalaska

2.5 out of 5
Price was $780, price is now $711 per person
$711
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to La Crosse (LSE)
9/10 Wonderful! (1,556 reviews)
We arrived to a surprise free upgrade to a king bedroom with whirlpool tub in the room! Free breakfast each morning was delicious and had a great variety -pancales, eggs, potatoes, cereal, pastries, breads, coffee, juice etc. The pool and HUGE hot tub were beautiful! The giant desktop bell is super fun! The property is very well maintained, clean and has a woodsy, rustic feel!

Reviewed on May 28, 2026

Don't see what you're looking for?
See all available trips from Columbus to Portland
View all trips

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
$104 nightly
The price is $119 total per night from Jun 3 to Jun 4
$119 total
Jun 3 - Jun 4
Total with taxes and fees
9/10 Wonderful! (1,549 reviews)
"We arrived to a surprise free upgrade to a king bedroom with whirlpool tub in the room! Free breakfast each morning was delicious and had a great variety -pancales, eggs, potatoes, cereal, pastries, breads, coffee, juice etc. The pool and HUGE hot tub were beautiful! The giant desktop bell is super ..."

Reviewed on May 28, 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
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Jun 14 to Jun 15
$81 total
Jun 14 - Jun 15
Total with taxes and fees
8.4/10 Very Good! (1,002 reviews)
"We loved our stay here! The coffee and tea station was appreciated, the pool was maintained well and a great size. This is an older hotel, but has been renovated and is well-maintained! The staff is so helpful! The breakfast bar was awesome! We will be back."

Reviewed on May 28, 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
$72 nightly
The price is $80 total per night from Jun 8 to Jun 9
$80 total
Jun 8 - Jun 9
Total with taxes and fees
8.6/10 Excellent! (1,001 reviews)
"The place smells!"

Reviewed on May 28, 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.

Find the Best Portland Vacation Packages

Portland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
La Crosse Municipal Airport (LSE)
Population
1,050
Max Temp Winter
25ºF
Max Temp Summer
75ºF

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Portland vacation package cost?
You can snap up a vacation package to this destination from $675 on Expedia. But how much your vacation 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?
January, February and November are great times to search for cheap Portland vacation packages. Choosing to travel in less busy months means you can generally find reduced prices on flights and hotels.
How many days is enough for Portland?
Typically, a handful of days is enough to see the major attractions during your Portland vacation. But if you want to have more time to rest or take day trips, think about extending your itinerary.
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 vacation package as soon as possible.
Is it cheaper to book a Portland vacation as a package?
You can enjoy significant savings on your Portland retreat by booking a customized vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Portland?
If you have your Portland vacation 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.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
Secure your dream escape to Portland with Expedia's Book Now, Pay Later vacations. No need to save up or wait for your next payday — we've partnered with online lender Affirm to give you flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily budget for your trip and snap up bargains before they sell out.

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.