Overlook Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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Your Overlook Vacation

Book a tailored Overlook vacation package that includes everything you need without any unnecessary extras. Good for shopping, nightlife and bars and pubs, consider staying in the neighborhood of Mississippi District. Ready to get out and explore? Oregon Zoo, Portland State University and Portland Japanese Garden are a few of the top places to visit during your trip to Overlook. Your perfect Overlook vacation is clicks away. Search airfares, hotels and more on Expedia for an adventure that's tailored to suit your travel style.

Top Holiday Package Deals in Overlook

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

Sentinel Hotel

5 out of 5
Downtown Portland
Price was CA $727, price is now CA $527 per person
CA $527
per person
Sep 30 - Oct 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
8.8/10 Excellent! (1,000 reviews)
I always love staying at the Sentinel. The location is wonderful, the rooms are special, the staff is warm, and the restaurants are excellent!

Reviewed on Aug. 14, 2025

Coast River Inn by OYO Seaside

Coast River Inn by OYO Seaside

2 out of 5
Price was CA $805, price is now CA $622 per person
CA $622
per person
Nov 8 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Portland (PDX)
8.4/10 Very Good! (1,004 reviews)
Expensive for a very basic motel.

Reviewed on Aug. 27, 2025

WorldMark Portland - Waterfront Park

WorldMark Portland - Waterfront Park

2.5 out of 5
Downtown Portland
Price was CA $821, price is now CA $638 per person
CA $638
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.8/10 Excellent! (56 reviews)
I liked to location. It put me in the middle of all that downtown PDX offers. That said, I would not stay here again. The room walls were thin and the hallways noisy. The room heater also did not work. I was given a small space heater, but that didn't heat the room. My main complaint is that this is actually a timeshare, and so the steady push for me to participate in a timeshare presentation was pretty incessant. Every interaction with staff lead to a pitch, to the point it felt very inauthentic to just have a normal conversation. I had to clearly say that I wasn't interested in order for the sales pitch to stop. I didn't like it.

Reviewed on Feb. 9, 2025

District Hotel by OYO Portland Convention Center

District Hotel by OYO Portland Convention Center

2 out of 5
Northeast Portland
Price was CA $685, price is now CA $539 per person
CA $539
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
6.6/10 (1,001 reviews)
Old shilo inn. Needs renovations

Reviewed on Jun. 5, 2025

The Hoxton Portland

The Hoxton Portland

4 out of 5
Downtown Portland
Price was CA $685, price is now CA $552 per person
CA $552
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
8.8/10 Excellent! (1,003 reviews)
Great hotel but downtown Portland can be challenging

Reviewed on Aug. 27, 2025

Where to stay in Overlook

Find the best Overlook areas and neighborhoods for the activities you enjoy most. Learn more about Overlook
Downtown Portland - South Waterfront which includes boating, a bay or harbour and picnicking

Downtown Portland

4.5/5(545 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

Overlook Hotel Deals

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 $163 per night from Sep 3 to Sep 4
CA $163
CA $191 total
Sep 3 - Sep 4
includes taxes & fees
DoubleTree by Hilton Hotel Portland
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
The price is CA $154 per night from Sep 2 to Sep 3
CA $154
CA $180 total
Sep 2 - Sep 3
includes taxes & fees
8.6/10 Excellent! (1,952 reviews)
"Over all not bad"

Reviewed on Aug. 24, 2025

Courtyard by Marriott Portland City Center
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 $142 per night from Sep 1 to Sep 2
CA $142
CA $166 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,725 reviews)
"The location is super, there is a park across the street, food and max rail stop are walking distance. The staffs were nice and helpful. The bed and pillow are nice. The only downside is the coffee in the room were not taste good. One time when I asked decaf, she gave me starbucks, that's nice. They ..."

Reviewed on Aug. 24, 2025

The Paramount Hotel
See all 2,708 properties in Overlook
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
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Frequently asked questions

How much does an Overlook vacation package cost?
Our Overlook vacation packages, which begin at just CA $527, are the easiest way to save big bucks. Pick your favorite hotels, flights and rental car to create your dream escape.
How do I get a cheap travel package to Overlook?
Our Overlook vacation packages promise plenty of savings for the savvy globetrotter. For the best deal, simply combine your flights, hotels and extras (such as activities) into a handy package. But cheap prices are just the beginning of your next amazing adventure. Book with Expedia and and you'll have over 550 airlines and 1,000,000 hotels across the globe to pick from. No matter your style, there's a package here just for you.
Where should I stay in Overlook?
Most visitors who travel to Overlook include Oregon Zoo and Portland State University on their must-see lists. Why not select a hotel that's close to these great attractions?
What are the top hotels in Overlook?
Economy INN and Private House With 3 Suites + Detached Living Room. Modern are among the most sought-after properties in Overlook. Why not look up the amenities and rates at each and then make up your mind?
How far in advance should I book my Overlook vacation?
It can be hard to know when is the ideal time to book your Overlook trip. But generally the earlier you book, the cheaper the prices. In some cases, you can book your flights and hotels nearly 12 months before your departure date. If you're eager to escape on a last-minute getaway, no need to panic! There are unbeatable deals posted on Expedia every single day.
What does an Expedia Overlook travel package include?
With Expedia, you can choose any combination of hotels, car rentals and flights to build your perfect Overlook travel package. Once you've made your booking, you can add on the fun things like tours and activities. Remember, the more you bundle, the greater the savings!
What should I know before booking an Overlook travel package?
When you book your flights, hotels and car rentals together, you'll score great discounts. Whether you're planning a rural escape in a cottage or want to stay in a convenient hotel in the city, Expedia can make it happen for less.
Can I choose my airline with an Overlook Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Overlook vacation package?
You sure can, and we're here to help. You may be able to cancel or change your Overlook vacation package at no cost if you booked in the last 24 hours. But you may incur a fee from your airline, hotel or car rental company for older bookings. If life gets in the way of your vacation, visit our Customer Service Portal for more information.

Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

CA $120
per adult
98% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $117
per traveller
96% of travellers recommend
Half-Day Multnomah Falls & Gorge Waterfalls Tour
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Willamette River 2.5-hour Dinner Cruise

CA $175
per adult
96% of travellers recommend
Portland: Willamette River 2.5-hour Dinner Cruise
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.