Overlook Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

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.
Park Lane Suites and Inn

Park Lane Suites and Inn

2.5 out of 5
Southwest Portland
Price was CA $1,069, price is now CA $769 per person
CA $769
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
8.8/10 Excellent! (1,866 reviews)
Check in was easy, but don’t come in with your bags until you know where you’ll be - we were in the motel-style building across the street from the suites. Beds were comfy and I slept well - in spite of the absolutely crazy noise and shaking of the building from people walking up and down the stairs and along the walkways outside of the rooms. So disorienting and LOUD and I’ve never experienced anything like this at a motel before. Like a herd of very rude elephants. 😑 🐘Thankfully things settled down later in the night. I could probably put up with this in the future given the price of the room, but it would have been nice to know how noisy it is. I whipped the door open when I first heard/felt this because I genuinely thought someone must have fallen and injured themselves.

Reviewed on Aug 5, 2026

Hotel deLuxe

Hotel deLuxe

4 out of 5
Downtown Portland
Price was CA $1,142, price is now CA $789 per person
CA $789
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
8.6/10 Excellent! (1,077 reviews)
Stuff is friendly , good location !

Reviewed on Aug 5, 2026

Heathman Hotel

Heathman Hotel

4.5 out of 5
Downtown Portland
Price was CA $1,135, price is now CA $786 per person
CA $786
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
9.2/10 Wonderful! (1,018 reviews)

The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,292, price is now CA $921 per person
CA $921
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
9.2/10 Wonderful! (1,006 reviews)
The staff was very accommodating.

Reviewed on Aug 3, 2026

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Price was CA $1,182, price is now CA $843 per person
CA $843
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
9.2/10 Wonderful! (2,333 reviews)

Where to stay in Overlook

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

Overlook 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 $157 per night from Aug 30 to Aug 31
CA $157
CA $183 total
Aug 30 - Aug 31
includes taxes & fees
The Paramount Hotel
Oxford Suites Portland - Jantzen Beach

Oxford Suites Portland - Jantzen Beach

3 out of 5
12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $131 per night from Aug 18 to Aug 19
CA $131
CA $169 total
Aug 18 - Aug 19
includes taxes & fees
9/10 Wonderful! (1,648 reviews)
"I would stay again"

Reviewed on Aug 5, 2026

Oxford Suites Portland - Jantzen Beach
The Duniway Portland A Hilton Hotel

The Duniway Portland A Hilton Hotel

4.5 out of 5
545 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Sep 4 to Sep 5
CA $218
CA $253 total
Sep 4 - Sep 5
includes taxes & fees
The Duniway Portland A Hilton Hotel
See all 2,849 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family 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 $769, 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.

Stay near popular Overlook attractions

Swan Island

8.4/10 (26 reviews)
You can find out about the history of Portland when you stop by Swan Island. Stroll along the riverfront or visit the shops in the area.
See properties

Things to do

Half-Day Multnomah Falls & Gorge Waterfalls Tour

Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $115
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 $125
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

CA $183
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
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.