Southwest Hills Vacation Packages

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

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Your Southwest Hills Vacation

The best way to experience this city is with a customized Southwest Hills vacation package. Base yourself in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining or choose someplace else — our package deals are all about you. Make your trip to Southwest Hills even more fun by going sightseeing. Oregon Zoo, Portland State University and Portland Japanese Garden are some of the leading attractions you'll want to explore. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Southwest Hills vacation is simple with Expedia.

Top Holiday Package Deals in Southwest Hills

Price found within the past 48 hours. Click for updated prices.
The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,114, price is now CA $819 per person
CA $819
per person
Jul 9 - Jul 13
found 23 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PDX)
9.2/10 Wonderful! (1,004 reviews)
Great location and great staff from the registration desk to the food service to room service to valets! Such kind and helpful people!

Reviewed on Apr 21, 2026

Bowline Hotel

Bowline Hotel

4 out of 5
Price was CA $1,638, price is now CA $1,225 per person
CA $1,225
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
9.4/10 Exceptional! (1,002 reviews)
The drinks were beautiful, along with the view at the bar. Our room was beautiful and the coffee was GREAT! Everything was perfect from start to end. One person working the bar could have been more pleasant - dark-headed girl. Smiling would help out a lot. We loved it there. We think the sea walrus should be named and they should have a cam-same thing with all of the ships...we learned so much watching them from our window and looking to see what flag they are flying. We thought that would be another fun thing the hotel could do

Reviewed on Apr 27, 2026

Cannon Beach Hotel Collection

Cannon Beach Hotel Collection

3.5 out of 5
Downtown Cannon Beach
Price was CA $1,539, price is now CA $1,171 per person
CA $1,171
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
9.2/10 Wonderful! (1,075 reviews)
Helpful staff, great location, comfortable room

Reviewed on Apr 28, 2026

The Tillamook Inn

The Tillamook Inn

2 out of 5
Price was CA $1,291, price is now CA $1,004 per person
CA $1,004
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
8/10 Very Good! (1,122 reviews)
The property is great and clean. Beds are comfy, but the pillows are too thick and firm. Went across the street to Fred Meyer and got 2 of my own to use. All in all a nice place to stay and conveniently located close to everything!!

Reviewed on Apr 27, 2026

Inn at Haystack Rock

Inn at Haystack Rock

2.5 out of 5
Downtown Cannon Beach
Price was CA $1,847, price is now CA $1,446 per person
CA $1,446
per person
Jun 24 - Jun 28
found 19 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
8.6/10 Excellent! (1,003 reviews)
We enjoyed our stay in a clean and comfortable room. It was a short walk to the beach to watch the sunset. The courtyard is charming. I would stay here again.

Reviewed on Apr 24, 2026

Where to stay in Southwest Hills

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

Downtown Portland

1 out of top 10 points of interest in this area
4.5/5(557 area reviews)

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.

Find hotels in Downtown Portland

Southwest Hills Hotel Deals

The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from May 3 to May 4
CA $145
CA $169 total
May 3 - May 4
includes taxes & fees
9.2/10 Wonderful! (3,335 reviews)
Spotless clean, and spacious. I’d definitely love to stay again.

Reviewed on Apr 26, 2026

The Paramount Hotel
Country Inn & Suites by Radisson, Portland International Airport, OR

Country Inn & Suites by Radisson, Portland International Airport, OR

3 out of 5
7025 NE Alderwood Rd Portland OR
Fully refundable
The price is CA $138 per night from May 12 to May 13
CA $138
CA $161 total
May 12 - May 13
includes taxes & fees
8.8/10 Excellent! (2,772 reviews)
Checkin was worrysome. Key card did not work X 3. Maintenance came to "check batteries" and found it was locked from the inside. ???? made us concerned re: security. moved us to another room. Housekeeping came by first morning- said they would come back with towels. Never got clean towels and had ...

Reviewed on Apr 27, 2026

Country Inn & Suites by Radisson, Portland International Airport, OR
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
1000 NE Multnomah Street Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from May 12 to May 13
CA $156
CA $182 total
May 12 - May 13
includes taxes & fees
8.6/10 Excellent! (1,038 reviews)
All perfect

Reviewed on Apr 27, 2026

DoubleTree by Hilton Hotel Portland
See all 2,909 properties in Southwest Hills
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 Southwest Hills vacation package cost?
Get set to book, because a getaway to Southwest Hills starts from just CA $819. When you bundle your hotels, flights and car rentals into a vacation package, you'll pick up the best bargains.
How do I get a cheap travel package to Southwest Hills?
Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into a Southwest Hills vacation package and save. Score even bigger bargains when you include extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your way. We offer over 550 partner airlines and 1,000,000 properties across the world, so that everyone has an opportunity to travel and live out those vacation fantasies.
Where should I stay in Southwest Hills?
Most visitors to Southwest Hills include Oregon Zoo and Portland State University on their bucket lists. Why not go for a hotel near these fantastic attractions?
What are the top hotels in Southwest Hills?
Castle Like Home In Sw Pdx, Close To Downtown and Spacious Gathering Spot In Portland Heights For Family And Friends are among the most popular hotels in Southwest Hills. Why not have a look at the amenities and rates at each and then make a decision?
How far in advance should I book my Southwest Hills vacation?
Reward yourself with the widest variety at the cheapest prices by booking your Southwest Hills adventure nice and early. Air carriers typically publish tickets anywhere up to 12 months in advance, so start locking things in ASAP. Having said that, Expedia is dedicated to providing you with the best deals around, so it's never a bad time to book your dream vacation!
What does an Expedia Southwest Hills travel package include?
Expedia has everything you need to organize your Southwest Hills getaway, but how your package is structured is totally up to you. Choose from any combination of rental cars, flights and hotels. Searching for some tours or activities to keep you on the go? Once you've made your booking, you can add them too. No matter your style, there's a vacation package to match your needs.
What should I know before booking a Southwest Hills travel package?
Our prices are already low. However, you'll grab even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll always get transparent pricing and lots of choice.
Can I choose my airline with a Southwest Hills Expedia vacation package?
Yes, you sure can. We have more than 550 airline partners throughout the world, so fly with the carrier that best fits your budget and traveling style.
If I'm not able to travel, can I cancel my Southwest Hills vacation package?
If your vacation plans in Southwest Hills have changed, it's comforting to know that it's possible to cancel your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. To find out more, visit our Customer Service Portal.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.