Southwest Portland Vacation Packages

Top Holiday Package Deals in Southwest Portland

Price found within the past 48 hours. Click for updated prices.

Hotel Eastlund, BW Premier Collection

Northeast Portland

CA $986

per person

Jan 24 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (2,257 reviews)

1 hr delayed check in due to “our room still being cleaned” with no real updates on how long till it was ready. Mind you check in is at 4-5 I arrived 3:55pm didn’t check in until 5:10pm. While others were gettin checked in right away. Once I do get checked in l find vomit or poop on the bathroom door boogers on the walls and make up down the bathroom walls. I sprayed the hell out of the rest of the room with Lysol I was so grossed out! Ohh and went to wash my hands our sinks were completely clogged too 🤦🏽‍♀️. The delay in check in caused me to miss VERY IMPORTANT MEDICAL needs that caused me to ultimately become too ill to enjoy the concert I looked forward to for 6 months and had to leave and check out not even 4 hours later. Staff was doin their best and did comped my parking( $43 by the way) and let us leave at 4pm for a check out and take whatever we wanted from the little store as a sorry for the check in delay but tbh I won’t be coming back or recommending this place. I drove 2hrs missed something I looked forward to for months and ended up very ill from this delay. The view and front desk people were nice and at least 🤷🏽‍♀️

Reviewed on Nov 9, 2026

Mark Spencer Hotel

Downtown Portland

CA $1,005

per person

Jan 24 - Jan 30

found 1 day ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (2,515 reviews)

Quick check in, nice staff, everything was good.

Reviewed on Nov 11, 2026

Holiday Inn Express Newberg - Wine Country by IHG

CA $1,188

per person

Jan 3 - Jan 7

found 14 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

8.8/10 Excellent! (773 reviews)

The room was spacious comfortable, and the staff was great!

Reviewed on Nov 11, 2026

Inn at Otter Crest

CA $1,336

per person

Dec 27 - Dec 31

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Portland (PDX)

9.2/10 Wonderful! (1,808 reviews)

Hyatt Regency Portland at the Oregon Convention Center

Northeast Portland

CA $1,268

per person

Jan 3 - Jan 7

found 14 hours ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

9.4/10 Exceptional! (1,880 reviews)

Where to stay in Southwest Portland

Find the best Southwest Portland areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Portland

A theater marquee with 'Portland' and 'An Evening with Crosby, Stills & Nash' written on it.

Downtown Portland

Explore the Portland Art Museum, Oregon Historical Society, and Tom McCall Waterfront Park in this central business district with high-rise buildings. Enjoy walkable streets, and easily access public transportation like MAX light rail and Portland Streetcar.

Southwest Portland Hotel Deals

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $146

CA $170 total

Dec 1 - Dec 2

includes taxes & fees

9.2/10 Wonderful! (3,783 reviews)

"Friendly staff. Comfortable bed and nice shower. Unfortunately no coffee maker in the room."

Reviewed on Nov 11, 2026

Mark Spencer Hotel

409 Sw 11th Ave Portland OR

CA $148

CA $172 total

Nov 16 - Nov 17

includes taxes & fees

9.2/10 Wonderful! (2,554 reviews)

"Quick check in, nice staff, everything was good."

Reviewed on Nov 11, 2026

Heathman Hotel

1001 SW Broadway Portland OR

Fully refundableReserve now, pay when you stay

CA $110

CA $177 total

Nov 25 - Nov 26

includes taxes & fees

See all 3,035 properties in Southwest 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 Southwest Portland vacation package cost?

Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Southwest Portland from just CA $986. And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.

How do I get a cheap travel package to Southwest Portland?

Browse and lock in everything in one place with our Southwest Portland vacation packages. You'll find deals on hotels, flights, tours and more that'll keep your bank account happy and your adventurous spirit alive. And, with more than 550 air carriers and 1,000,000 hotel options worldwide to pick from, there are endless opportunities to mix and match as you please.

How far in advance should I book my Southwest Portland vacation?

Earlier is always better. Air carriers generally release flights up to 12 months prior to departure, and this is a great opportunity to score some of the cheapest prices. Just been told you need to take some vacation time next month? That's alright! Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at an affordable price.

What does an Expedia Southwest Portland travel package include?

Hotels, rental cars and flights — we have them well covered. With Expedia, you can shape your Southwest Portland travel package just the way you want. All you have to do is work out what you need. Once you've made your booking, you can add on extras like experiences and activities. The more you bundle, the greater the savings!

What should I know before booking a Southwest Portland travel package?

Discover deals to match your budget with an Expedia package. Airfares, hotels, rental cars — we have them all. You'll save a tidy sum just by bundling your bookings. Whether you're taking off on a snow and ski adventure or venturing someplace warm, your perfect getaway is only a few clicks away.

Can I choose my airline with a Southwest Portland Expedia vacation package?

Yes, you can. We have more than 550 partner airlines all over the world, so fly with the carrier that suits your needs.

If I'm not able to travel, can I cancel my Southwest Portland vacation package?

Plans can change in the blink of an eye, so yes, you can. You may be able to change or cancel your Southwest Portland vacation package at no cost if you've booked in the last 24 hours. For bookings older than that, you can still make changes, but your car rental company, airline or hotel may charge additional fees. Want more information? Look up our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.