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*

  • Find the right fit

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

  • Rest easy

    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.
The Nines, a Luxury Collection Hotel, Portland

The Nines, a Luxury Collection Hotel, Portland

5 out of 5
Downtown Portland
Price was CA $1,238, price is now CA $961 per person
CA $961
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PDX)
9.2/10 Wonderful! (1,004 reviews)
Immaculate and beautiful stay in the heart of Portland.

Reviewed on Jun 17, 2026

Hotel deLuxe

Hotel deLuxe

4 out of 5
Downtown Portland
Price was CA $1,203, price is now CA $965 per person
CA $965
per person
Jul 29 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PDX)
8.6/10 Excellent! (1,039 reviews)
Atmosphere was perfect with the theme of hotel. The pics the colors everything. We had a fantastic time. Didn’t have time to hit happy hour but breakfast in the morning was amazing and hit the spot. Can’t want to stay there again.

Reviewed on Jun 3, 2026

Inn at Haystack Rock

Inn at Haystack Rock

2.5 out of 5
Downtown Cannon Beach
Price was CA $1,892, price is now CA $1,527 per person
CA $1,527
per person
Sep 2 - Sep 6
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
8.6/10 Excellent! (1,003 reviews)
This place is cute and charming. The rooms are equipped with all you need, but small/ cozy. We enjoyed it and would stay again. But thing to consider when booking. The only mirror/ area to get ready/ brush your teeth is in the kitchenette area. The bathroom doesn’t have a mirror or sink. We were in cottage 2 and the angle of the tv/ bed made it hard to enjoy without a stiff neck at times. The property and room are well maintained. Only encountered one employee at check in, other than that I didn’t really see any staff. There is only enough parking for one car per unit/ no real guest parking if you were planning for that. Review says to rate the amenities but I do not recall this property having any?! If they did the check-in staff did not mention them nor did I see them besides they do have free wifi. And the room had a refrigerator, microwave, toaster, coffee pot, and misc kitchen utensils for two. And we noticed it’s one of the few places in the area that do not allow dogs when 95% of the town is dog friendly from what we saw.it is centrally located to both north and south parts of cannon beach. All is in walking distance and the beach is a short walking block away (straight shot). And most importantly it is moments away from the Iconic Haystack rock. A must see!

Reviewed on Jun 16, 2026

Moonlight by Avantstay Modern Home w/ Views & Direct Access to Rockaway Beach

Moonlight by Avantstay Modern Home w/ Views & Direct Access to Rockaway Beach

3 out of 5
Price was CA $3,546, price is now CA $2,894 per person
CA $2,894
per person
Sep 2 - Sep 6
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
No reviews
Magic Tree House by Avantstay Fire Pit + Deck + Movie Room Walk to the Beach

Magic Tree House by Avantstay Fire Pit + Deck + Movie Room Walk to the Beach

3 out of 5
Price was CA $2,425, price is now CA $1,998 per person
CA $1,998
per person
Sep 2 - Sep 6
found 4 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PDX)
No reviews

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 $158 per night from Jul 7 to Jul 8
CA $158
CA $184 total
Jul 7 - Jul 8
includes taxes & fees
9.2/10 Wonderful! (3,451 reviews)
"A no frills room, bed and pillows were comfortable. Hotel offered valet service that allowed for unlimited in/out privileges. Walking distance to food establishments and shopping."

Reviewed on Jun 18, 2026

The Paramount Hotel
Hyatt House Portland/Downtown

Hyatt House Portland/Downtown

3 out of 5
2080 SW River Drive Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Jun 21 to Jun 22
CA $196
CA $227 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (2,590 reviews)
"It’s a great facility with very nice size rooms but even tho some of the stuff were amazing, also one of the employees decided to help herself to some very expensive tequila that I had sitting on the counter"

Reviewed on Jun 18, 2026

Hyatt House Portland/Downtown
Holiday Inn Airport - Portland by IHG

Holiday Inn Airport - Portland by IHG

3 out of 5
8439 Ne Columbia Blvd Portland OR
Fully refundable
The price is CA $114 per night from Jul 8 to Jul 9
CA $114
CA $132 total
Jul 8 - Jul 9
includes taxes & fees
8/10 Very Good! (2,992 reviews)
"Room seemed clean but decor is outdated and beat up, everything needs a little update. The hallways felt old and dated. The luggage cart and elevator combo were a little frustrating. It served our purpose of a last minute place to stay and we did receive a Mountain View on a high floor as promised ..."

Reviewed on Jun 18, 2026

Holiday Inn Airport - Portland by IHG
See all 2,829 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 $961, 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

8.4/5 (26 reviews)
You can find out about the history of Portland when you stop by Swan Island. Stroll along the beautiful beaches or visit the shops in the area.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.