Overlook Vacation Packages

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  • 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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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.
Capitol Hill Motel

Capitol Hill Motel

2.5 out of 5
Southwest Portland
Price was CA $1,010, price is now CA $789 per person
CA $789
per person
Jul 4 - Jul 9
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.2/10 Wonderful! (850 reviews)
Basic hotel price is reasonable and the room was clean. I could hear the road but given it's proximity to 5 and Capitol it's to be expected.

Reviewed on Apr 19, 2026

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Price was CA $1,186, price is now CA $931 per person
CA $931
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.2/10 Wonderful! (2,128 reviews)
Staff was friendlyyyy. They were all so cool! The hotel is a bit older but they modernized it without taking away its charm. The bed was sooo comfortable & sheets were so soft I was looking for the brand to get them at home! I’ll definitely stay again!

Reviewed on Apr 29, 2026

Dossier Hotel

Dossier Hotel

4.5 out of 5
Downtown Portland
Price was CA $1,168, price is now CA $919 per person
CA $919
per person
Jun 14 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9.4/10 Exceptional! (1,397 reviews)
We stayed on the 5th floor. It was extremely noisy - not sure if the room given was close to a certain machine - but sleeping was horrible. It was interrupted by extreme noise. We won’t be back. More cleaning is needed in the room, in regards to dusting. However, the hotel looks very quaint.

Reviewed on Apr 29, 2026

AC Hotel by Marriott Portland Downtown, OR

AC Hotel by Marriott Portland Downtown, OR

3.5 out of 5
Downtown Portland
Price was CA $1,189, price is now CA $948 per person
CA $948
per person
Jul 4 - Jul 9
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
9/10 Wonderful! (1,010 reviews)
The staff at the front desk were great, but our concerns were the following: 1. The breakfast buffet was not worth the $15.95 charge. 2. House keeping was very poor. They did not come into the room during our stay, except once, and because we were in the room at that time, they never returned at a later time. We had been staying out late due to our outdoor treks, and we did not return to the room until very late at night, so it was unpleasant to know that upon our arrival back to the room in the late hours, the towels and linens were not replaced. There are signs in the bathroom stating if we wanted the towels replaced, then to leave them on the floor, and we did. Unfortunately, the lack of house keeping dampened our experience here. 3. Lastly, we were charged a valet fee when we did not use the valet.

Reviewed on Apr 27, 2026

Hotel deLuxe

Hotel deLuxe

4 out of 5
Downtown Portland
Price was CA $1,171, price is now CA $934 per person
CA $934
per person
Jul 4 - Jul 9
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PDX)
8.6/10 Excellent! (1,011 reviews)
I liked everything about this place. Staff was very courteous and good at their jobs. From the front desk, to housekeeping, to the suits. Chill atmosphere, and room was very nice and clean. I would highly recommend staying here if your heading to Portland. Will definitely stay here again in the near future. Thank you Hotel De Luxe

Reviewed on Apr 29, 2026

Where to stay in Overlook

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

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 $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! (3,342 reviews)
Room was clean

Reviewed on Apr 30, 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 $140 per night from May 31 to Jun 1
CA $140
CA $164 total
May 31 - Jun 1
includes taxes & fees
8.8/10 Excellent! (2,777 reviews)
They hadn’t changed the sheets in our room, but changed us to a different room, no problem

Reviewed on May 1, 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 27 to May 28
CA $156
CA $182 total
May 27 - May 28
includes taxes & fees
8.6/10 Excellent! (1,042 reviews)
I’ve stayed at the Double Tree many times over the years, and has always been amazing. This time was less so. The check-in staff was unfriendly and not very helpful. Getting any information out of them was like pulling teeth. When we got to our room, even though we had booked a room with a queen, ...

Reviewed on Apr 30, 2026

DoubleTree by Hilton Hotel Portland
See all 2,828 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
Family Vacations

Frequently asked questions

How much does an Overlook vacation package cost?
Our Overlook vacation packages, which begin at just CA $789, 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 Through Downtown

CA $123
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Full-Day Guided Oregon Coast Tour from Portland

Full-Day Guided Oregon Coast Tour from Portland

CA $192
per adult
100% of travellers recommend
Full-Day Guided Oregon Coast Tour from Portland
Picture 11 for Activity Portland: Champagne Brunch Cruise on Willamette River

Portland: Brunch Cruise on Willamette River

CA $145
per adult
92% of travellers recommend
Portland: Brunch Cruise on 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.