Overlook Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith 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.
Skamania Lodge
CA $1,472
per person
Dec 23 - Dec 29
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PDX)
9.2/10 Wonderful! (1,041 reviews)
Room was spacious and clean.
Jacuzzi and sauna in each locker room. Nice!
Food was good but service for breakfast very slow.
Wonderful views from the lobby and patio.
Reviewed on Sep 30, 2026
Bowline Hotel
CA $1,327
per person
Nov 7 - Nov 11
found 21 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.4/10 Exceptional! (1,004 reviews)
The property is situated on the edge of the Pacific Ocean. It’s stunning! The room was large with high ceilings and an industrial design, which I loved. The hotel is very convenient to downtown Astoria and easily walkable. The sea lions are a bit noisy but the hotel offers ear plugs and a white noise machine that drowned out their noise. The staff is friendly and helpful. I didn’t care for the trans flag. I’d rather see an American flag. I don’t need to be reminded of what anybody prefers in the privacy of their bedroom.
Reviewed on Sep 30, 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
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.
Northeast Portland
1 out of top 10 points of interest in this area
Inner Northeast Portland boasts shopping areas like Lloyd District and Alberta Arts District, while the area near Burnside Bridge offers a lively nightlife with bars such as The Chesterfield and music venues like The Doug Fir Lounge.
Pearl District
1 out of top 10 points of interest in this area
Discover art galleries like Elizabeth Leach Gallery, dine at diverse restaurants, and unwind in public plazas such as Jamison Square. Easily navigate with the Portland Streetcar and explore nearby iconic Powell's City of Books.
Southeast Portland
Stretching from the Willamette River to Gresham, Southeast Portland boasts the scenic Mt. Tabor Park and the quirky Hawthorne district with its subculturally oriented shops. Don't miss exploring Reed College campus!
Southwest Portland
3 out of top 10 points of interest in this area
Downtown Portland boasts cultural, educational, and retail hotspots, with attractions like Tom McCall Waterfront Park, Portland Art Museum, and Pioneer Place mall. Enjoy pedestrian-friendly streets and unique residential areas in Southwest Portland.
Overlook Hotel Deals
The Paramount Hotel
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
CA $167
CA $195 total
Oct 20 - Oct 21
includes taxes & fees
Heathman Hotel
1001 SW Broadway Portland OR
Fully refundableReserve now, pay when you stay
CA $142
CA $214 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,081 reviews)
"Lovely charming room"
Reviewed on Sep 29, 2026
Country Inn & Suites by Radisson, Portland International Airport, OR
7025 NE Alderwood Rd Portland OR
Fully refundable
CA $152
CA $177 total
Oct 29 - Oct 30
includes taxes & fees
8.8/10 Excellent! (3,250 reviews)
"The room was clean and the bed was somewhat comfortable. The main elevator was down, which wasn't so bad for me but it wasn't good for those staying at the other end of the hotel. There was only one coffee packet , 2 would have been better. Oh and there is never enough cream and sugar. It was okay ..."
Reviewed on Sep 29, 2026
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.
Frequently asked questions
How much does an Overlook vacation package cost?
Our Overlook vacation packages, which begin at just CA $1,200, 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.
Overlook Park
After visiting Overlook Park, make a plan to see the other sights and activities in Portland. Stroll along the area's riverfront or experience its acclaimed theater scene.
Lindbergh's Beach
Commune with nature and explore the great outdoors at Lindbergh's Beach during your travels in Portland. Wander the area's riverfront or simply enjoy one of its top-notch restaurants.
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 great live music.
Interstate Firehouse Cultural Center
Enjoy an outing to Interstate Firehouse Cultural Center during your stay in Portland. Wander the riverfront and picturesque gardens in the area.
Patton Square Park
Patton Square Park is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Wander around the area's picturesque gardens or experience its acclaimed theater scene.
Things to do
Half-Day Multnomah Falls & Gorge Waterfalls Tour
CA $119
per traveller
96% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
CA $123
per adult
98% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
CA $196
per traveller
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.