Overlook Vacation Packages

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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.
Hyatt House Portland/Downtown

Hyatt House Portland/Downtown

3 out of 5
Downtown Portland
per person
Aug. 6 - Aug. 9
Roundtrip non-stop flight included
Victoria (YYJ) to Portland (PDX)
8.8/10 Excellent! (1,159 reviews)
Staff was extremely nice and pleasant, were from California and the hospitality was exceptional for this hotel

Reviewed on May 23, 2024

The Setting Inn Willamette Valley

The Setting Inn Willamette Valley

3.5 out of 5
Save 100% on your flight
per person
Jun. 30 - Jul. 7
Roundtrip flight included
Calgary (YYC) to Portland (PDX)
10/10 Exceptional! (62 reviews)
I was happy that there was a car charger. Beautiful location, very nice place to stay in Dundee

Reviewed on May 19, 2024

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
per person
Aug. 6 - Aug. 9
Roundtrip non-stop flight included
Victoria (YYJ) to Portland (PDX)
9.2/10 Wonderful! (1,066 reviews)
Would stay again. Comfortable bed, nice shower, fresh coffee in the lobby, great value for the price on a Friday night. Underground hotel parking was extremely tight, narrow spots with cement pillars everywhere, my only minor complaint.

Reviewed on May 19, 2024

La Bastide Bed & Breakfast

La Bastide Bed & Breakfast

3.5 out of 5
per person
Jun. 30 - Jul. 7
Roundtrip flight included
Calgary (YYC) to Portland (PDX)
10/10 Exceptional! (208 reviews)
Absolutely fabulous in every way! The property is decorated beautifully. The bed was extremely comfortable. The breakfast was delicious. The host, superb!

Reviewed on May 18, 2024

The Gaard House

The Gaard House

2 out of 5
per person
Jun. 30 - Jul. 7
Roundtrip flight included
Calgary (YYC) to Portland (PDX)
9.4/10 Exceptional! (18 reviews)
This was an amazing retreat for the weekend. Hospitality was off the charts and the breakfast was thoughtful and delicious. The property is breathtaking and close to everything we needed. We are basketball fans and the theatre room was an unexpected surprise that saw plenty of use for NCAA conference tournament games😁

Reviewed on Mar. 11, 2024

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 showing picnicing, boating and a bay or harbor

Downtown Portland

1 out of top 10 points of interest in this area
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 hotel + flight trips 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 $116 per night from May 26 to May 27
CA $116
CA $175 total
includes taxes & fees
May 26 - May 27
9.2/10 Wonderful! (1,871 reviews)
"This is a well run establishment in a convenient location."

Reviewed on May 20, 2024

The Paramount Hotel
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 $108 per night from Jun. 9 to Jun. 10
CA $108
CA $127 total
includes taxes & fees
Jun 9 - Jun 10
8.6/10 Excellent! (1,017 reviews)
"Parking was a problem."

Reviewed on May 21, 2024

Courtyard by Marriott Portland City Center
Moxy Portland Downtown
Moxy Portland Downtown
3 out of 5
585 SW 10TH AVENUE, Portland, OR
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from May 28 to May 29
CA $126
CA $146 total
includes taxes & fees
May 28 - May 29
8.8/10 Excellent! (669 reviews)
"Hotel was super clean and staff was friendly."

Reviewed on May 20, 2024

Moxy Portland Downtown
See all 2,591 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

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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 $666, 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.

Discover the most popular places to visit in Overlook

Image for Swan Island

Swan Island

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.

Swan Island
Image for Overlook Park

Overlook Park

Explore the lovely green spaces of Overlook Park and also enjoy the biking trails in Portland. Wander around the area's picturesque gardens or experience its acclaimed theater scene.

Overlook Park
Image for Historic Overlook House

Historic Overlook House

You can find out about the history of Portland with a trip to Historic Overlook House. Stroll along the area's riverfront or experience its acclaimed art scene.

Historic Overlook House

Things to do

Image for Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-hour Lunch Cruise on the Willamette River

CA $116
Per adult
94% of travellers recommend
Portland: 2-hour Lunch Cruise on the Willamette River
Image for Northern Oregon Coast Day Trip to Cannon Beach Area

Northern Oregon Coast Day Trip to Cannon Beach Area

CA $188
Per adult
100% of travellers recommend
Northern Oregon Coast Day Trip to Cannon Beach Area
Image for Essential Portland Oregon Bike and E-Bike Tour!

Essential Portland Oregon Bike and E-Bike Tour!

CA $73
Per adult
Essential Portland Oregon Bike and E-Bike Tour!
See all activities in Portland

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.