Overlook Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Overlook Vacation

Book a vacation package to Overlook and discover everything this riverside neighborhood has to offer. Well known for its cycling, bars and pubs and dining, your next exciting adventure is waiting for you here. Hoping to explore the sights during your trip to Overlook? Don't miss nearby attractions like Portland Japanese Garden, Veterans Memorial Coliseum and Pioneer Courthouse Square. Don't just think about it — take action! Reserve your ultimate Overlook vacation with Expedia and experience travel your way.

The Latest Overlook Vacation Packages

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

Hotel deLuxe

4 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 12 - Aug 16
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
8.8/10 Excellent! (1,000 reviews)
We have stayed at this hotel a couple of times before. It’s in a great spot kind of tucked away from the hustle and bustle in the beautiful old building. The staff was extremely helpful and friendly. Great lobby area too.

Reviewed on May 24, 2024

Dossier Hotel

Dossier Hotel

4.5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 12 - Aug 16
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
9/10 Wonderful! (1,000 reviews)
Great hotel with a great location! Would highly recommend staying here ♥️

Reviewed on May 25, 2024

Mark Spencer Hotel

Mark Spencer Hotel

3 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 12 - Aug 16
found 19 hours ago
Roundtrip flight included
Denver (DEN) 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

Sentinel Hotel

Sentinel Hotel

5 out of 5
Downtown Portland
Save 100% on your flight
per person
Aug 12 - Aug 16
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Portland (PDX)
8.8/10 Excellent! (1,000 reviews)
Hotel was beautiful. Our room just felt a little run down. But the fire pit was cool.

Reviewed on May 25, 2024

Budget Inn Gladstone By OYO - Portland/Clackamas

Budget Inn Gladstone By OYO - Portland/Clackamas

2.5 out of 5
Jennings Lodge
Save 100% on your flight
per person
Aug 13 - Aug 19
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Portland (PDX)
5.8/10 (171 reviews)
Great place for the price - nice proprietors. We always stay here when we visit grandkids.

Reviewed on May 1, 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(4,488 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
9.2/10 Wonderful! (1,878 reviews)
"Great overall hotel!"

Reviewed on May 23, 2024

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The Paramount Hotel
Red Lion Hotel Portland Airport
Red Lion Hotel Portland Airport
3 out of 5
7101 NE 82nd Ave, Portland, OR
Fully refundableReserve now, pay when you stay
7/10 Good! (2,035 reviews)
"Good people and place. No marking for parking that was $10 per night also not advertised and the n a one way rd."

Reviewed on May 24, 2024

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Red Lion Hotel Portland Airport
Courtyard by Marriott Portland City Center
Courtyard by Marriott Portland City Center
3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundableReserve now, pay when you stay
8.6/10 Excellent! (1,026 reviews)
"Very friendly and helpful staff. Restaurant could have more choices ."

Reviewed on May 24, 2024

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Courtyard by Marriott Portland City Center
See all 2,597 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

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Overlook vacation package cost?
Our Overlook vacation packages, which begin at just $339, 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

$86
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

$139
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!

$54
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.