Crestwood Vacation Packages

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Your Crestwood Vacation

Lock in a Crestwood vacation package and prepare to experience the highlights of this city. Consider staying in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining. Make your trip to Crestwood even more fun and exciting by including some sightseeing. Oregon Zoo, Portland State University and Portland Japanese Garden are some of the most popular attractions you'll want to explore. Whoever you're going away with and whatever your bank balance, your dream Crestwood vacation is just clicks away with Expedia.

Top Holiday Package Deals in Crestwood

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel Portland - Pearl District

Cambria Hotel Portland - Pearl District

Pearl District
CA $635
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.8/10 Exceptional! (712 reviews)
Outstanding property! Very clean, perfect location, very friendly staff and the restaurant had amazingly delicious options! My absolute favorite part of my stay was the night cap time at the bar and not even for the drinks! Our bartender Chuck was one of the friendliest, most welcoming and knowledgeable people I met while in Portland! He truly put the icing on the cake for the stay.

Reviewed on Aug 14, 2026

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

Downtown Portland
CA $1,140
per person
Nov 7 - Nov 11
found 8 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PDX)
9.2/10 Wonderful! (1,007 reviews)
We were in town for a wedding. Very happy with not just the convenient location to everything, but the staff is amazing… from Valet to rooftop bar, every single staff member was friendly and helpful. The Bloody Mary from Urban Farmer was one of the best I ever had. As was the “shrimp toast” in rooftop Departure restaurant and bar. We highly recommend this hotel if you want to stay in Portland close to everything. Valet team/service made our stay 5-star. Without their hard work (crowd control, car retrieval, opening doors, loading bags, directing rides, travel tips, I can go on and on) this would be 4 star.

Reviewed on Aug 13, 2026

Portland's White House

Portland's White House

Northeast Portland
CA $974
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
No reviews
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

Northeast Portland
CA $861
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.6/10 Excellent! (1,182 reviews)
Everything

Reviewed on Aug 12, 2026

RiverPlace Hotel

RiverPlace Hotel

Downtown Portland
CA $737
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.2/10 Wonderful! (1,003 reviews)
I supposed to get 20% off when I dine at their restaurant. But they didn’t honor that.

Reviewed on Aug 13, 2026

Where to stay in Crestwood

Find the best Crestwood areas and neighborhoods for the activities you enjoy most. Learn more about Crestwood
Two people sitting on a blanket by a marina with boats docked in the background.

Downtown Portland

1 out of top 10 points of interest in this area

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
A forested area with a stone structure, wooden benches, and a pathway leading to a central point.

Northeast Portland

1 out of top 10 points of interest in this area

Inner Northeast Portland boasts shopping areas like Lloyd District and Alberta Arts District, while the area near Burnside Bridge offers a lively nightlife with bars such as The Chesterfield and music venues like The Doug Fir Lounge.

Find hotels in Northeast Portland
A street with a modern building featuring large murals, parked cars, and a café with outdoor seating.

Pearl District

Discover art galleries like Elizabeth Leach Gallery, dine at diverse restaurants, and unwind in public plazas such as Jamison Square. Easily navigate with the Portland Streetcar and explore nearby iconic Powell's City of Books.

Find hotels in Pearl District
A dinosaur statue in front of a building with a glass facade and the letters 'OMS' on it.

Southeast Portland

1 out of top 10 points of interest in this area

Stretching from the Willamette River to Gresham, Southeast Portland boasts the scenic Mt. Tabor Park and the quirky Hawthorne district with its subculturally oriented shops. Don't miss exploring Reed College campus!

Find hotels in Southeast Portland
A cable car system, a cityscape with high-rise buildings, a river, and a mountain in the background.

Southwest Portland

2 out of top 10 points of interest in this area

Downtown Portland boasts cultural, educational, and retail hotspots, with attractions like Tom McCall Waterfront Park, Portland Art Museum, and Pioneer Place mall. Enjoy pedestrian-friendly streets and unique residential areas in Southwest Portland.

Find hotels in Southwest Portland

Crestwood Hotel Deals

The Paramount Hotel

The Paramount Hotel

808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
CA $156
CA $182 total
Aug 23 - Aug 24
includes taxes & fees
9.2/10 Wonderful! (3,603 reviews)
"Include breakfast"

Reviewed on Aug 14, 2026

The Paramount Hotel
Oxford Suites Portland - Jantzen Beach

Oxford Suites Portland - Jantzen Beach

12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
CA $130
CA $167 total
Aug 23 - Aug 24
includes taxes & fees
9/10 Wonderful! (1,666 reviews)
"Hotel was great. Located close to i5. Lots of amenities. Very clean. Unfortunately hot tub was cold which we only found out when we tried to go into it. Even reception was ok - 1 free drink or 1 pop per person and soup with bread. Breakfast was ok - standard hotel breaky with hot and cold options. ..."

Reviewed on Aug 13, 2026

Oxford Suites Portland - Jantzen Beach
Hyatt Regency Portland at the Oregon Convention Center

Hyatt Regency Portland at the Oregon Convention Center

375 NE Holladay St Portland OR
Fully refundableReserve now, pay when you stay
CA $176
CA $245 total
Aug 23 - Aug 24
includes taxes & fees
Hyatt Regency Portland at the Oregon Convention Center
See all 2,925 properties in Crestwood
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 Crestwood vacation package cost?
Starting from a low CA $635, a vacation package is your gateway to affordable travel. Customize your Crestwood trip by selecting from our comprehensive range of flights, hotels and rental cars.
How do I get a cheap travel package to Crestwood?
One of the simplest ways to save money (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we've got them all covered. Choose a combination that suits you and watch your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer more than 550 airlines and 1,000,000 hotels across the globe, which lets you customize your Crestwood vacation.
Where should I stay in Crestwood?
A journey to Crestwood isn't over until you've seen Oregon Zoo and Portland State University. Reserve a room as close as possible for easy access to these fantastic sights.
How far in advance should I book my Crestwood vacation?
To land cheap prices, book as early as you can. Airlines generally release tickets, along with some of the lowest fares, nearly a year in advance. Hotels, car rental and activities should also be booked well in advance to avoid disappointment. If you've decided on a last-minute getaway to Crestwood, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia Crestwood travel package include?
Choose from any combination of rental cars, hotels and flights. Once you've made your booking, you can also add on tours and activities. Want to pick your fare class? That's easy to do too. The choice is yours when it comes to putting together your dream Crestwood getaway.
What should I know before booking a Crestwood travel package?
Get ready to save with an Expedia travel package. Bundle your flights, rental cars and hotels and unlock fantastic discounts. Hotels aren't your only option, though. Book with us and select from beach villas, cabins in the mountains and even castles and houseboats!
Can I choose my airline with a Crestwood Expedia vacation package?
With a vacation package, you're in control. Whether you're hoping to fly to Crestwood in economy or business class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.
If I'm not able to travel, can I cancel my Crestwood vacation package?
Plans can change unexpectedly, so yes. You may be able to amend or cancel your Crestwood vacation package for free if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your car rental company, hotel or airline may charge additional fees. Want more information? Have a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $114
per traveller
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

CA $124
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Full-Day Mount Hood & Multnomah Falls Tour

Full-Day Mount Hood & Multnomah Falls Tour

CA $188
per traveller
96% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.