Title: Overlook Vacation Packages | Holiday Packages & Trips 2026/2027 from  Expedia.ca

[Hotels in Overlook](https://expedia.ca/Overlook-Portland-Hotels.0-n553248635976386737-0.Travel-Guide-Filter-Hotels)[Flights to Portland](https://expedia.ca/Cheap-Flights-To-Portland.d178299.Travel-Guide-Flights)[Things to do in Portland](https://expedia.ca/Things-To-Do-In-Portland.d178299.Travel-Guide-Activities)[Overlook Car Rentals](https://expedia.ca/Car-Rentals-In-Overlook.d553248635976386737.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/bex-affinities/lodging.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Overlook Vacation Packages

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to CA $1,096 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](https://www.expedia.ca/Oregon-Zoo-Southwest-Portland.d502371.Vacation-Attraction), [Portland State University](https://www.expedia.ca/Portland-State-University-Southwest-Portland.d502369.Vacation-Attraction) and [Portland Japanese Garden](https://www.expedia.ca/Portland-Japanese-Garden-Southwest-Portland.d6080741.Vacation-Attraction) 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.

## Where to stay in Overlook

Find the best Overlook areas and neighborhoods for the activities you enjoy most. [Learn more about Overlook](https://expedia.ca/Portland-Overlook.dx553248635976386737)

![Downtown Portland - South Waterfront which includes boating, a bay or harbour and picnicking](https://images.trvl-media.com/place/6054571/ae055529-d7c3-4ca8-9f4a-92fe5da04874.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Portland&DestID=6054571&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Portland skyline on a crisp clear winter night. The Eastbank Esplanade is an ideal stroll the see this beautiful city at any hour of the day.
#Oregon #Portland #skyline #night #Eastbankesplanade](https://images.trvl-media.com/place/2759/9429211f-0e18-40d0-b016-76c7a17f3e83.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Northeast Portland](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Northeast%20Portland&DestID=553248635975749210&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![H2FWK3 USA, Oregon, Portland, Crystal Springs Rhododendron Garden, Rhododendrons bloom near waterfall and Crystal Springs Lake.. Image shot 2016. Exact date unknown.](https://images.trvl-media.com/place/6054579/766d569f-8b64-424f-a84c-b508daa4bf07.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Southeast Portland

1 out of top 10 points of interest in this area

 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! 

[Find hotel + flight trips in Southeast Portland](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Southeast%20Portland&DestID=6054579&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Pearl District which includes outdoor art](https://images.trvl-media.com/place/6161282/4b33f2da-dae4-4719-84d7-33ccbce026af.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Pearl District

4.5/5(43 area reviews)

 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. 

[Find hotel + flight trips in Pearl District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Pearl%20District&DestID=6161282&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Sunrise from the upper tram terminal at Oregon Health Science University. Timing is everything in photography. I have waited a year to get the right timing and weather for this shot. For those fortunate enough to ride the tram daily this is a common sight. Mount Hood in the background.](https://images.trvl-media.com/place/2759/b0fdb6c4-0320-45b0-b496-25cc741eb6e2.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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. 

[Find hotel + flight trips in Southwest Portland](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Southwest%20Portland&DestID=553248635074843098&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Overlook Hotel Deals

![The Paramount Hotel](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/001f8236_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $128

CA $149 total

Mar 9 - Mar 10

includes taxes & fees

9.2/10 Wonderful! (3,244 reviews)

Super close to restaurants and things to do. We saw a show at the Arlene schnitzer concert hall.

Reviewed on Mar 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=330558&PinnedHotelID=330558&HadPinnedHotel=true&regionId=553248635976386737)

![Park Lane Suites and Inn](https://images.trvl-media.com/lodging/1000000/30000/26100/26052/e03d5786_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Park Lane Suites and Inn

809 SW King Avenue Portland OR

Fully refundable

CA $107

CA $125 total

Mar 9 - Mar 10

includes taxes & fees

8.8/10 Excellent! (1,661 reviews)

Our suite was very well equipped, and very comfortable. Well worth the small extra cost. Also, there’s an elevator in the suites building, and none in the 2-storey building that houses the regular rooms. The area is quieter than we expected, which was nice. There’s a lot within easy walking distance ...

Reviewed on Mar 7, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=26052&PinnedHotelID=26052&HadPinnedHotel=true&regionId=553248635976386737)

![Cambria Hotel Portland - Pearl District](https://images.trvl-media.com/lodging/117000000/116860000/116853800/116853726/4e11abbd_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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Cambria Hotel Portland - Pearl District

165 NW Park Ave Portland OR

Fully refundable

CA $156

CA $181 total

Mar 29 - Mar 30

includes taxes & fees

9.8/10 Exceptional! (308 reviews)

Great place to stay and the staff was amazing! Would definitely recommend staying here, clean rooms and felt safe.

Reviewed on Mar 6, 2026

[](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%2F2026&selected=116853726&PinnedHotelID=116853726&HadPinnedHotel=true&regionId=553248635976386737)

[See all 2,873 properties in Overlook](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&regionId=553248635976386737)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does an Overlook vacation package cost?

### How do I get a cheap travel package to Overlook?

### Where should I stay in Overlook?

### What are the top hotels in Overlook?

### How far in advance should I book my Overlook vacation?

### What does an Expedia Overlook travel package include?

### What should I know before booking an Overlook travel package?

### Can I choose my airline with an Overlook Expedia vacation package?

### If I'm not able to travel, can I cancel my Overlook vacation package?

### Things to do

![Half-Day Multnomah Falls & Gorge Waterfalls Tour](https://mediaim.expedia.com/localexpert/377450/d9664a8a-791c-4b64-89e7-c4117f474489.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Half-Day Multnomah Falls & Gorge Waterfalls Tour

CA $116

per traveller

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/half-day-multnomah-falls-gorge-waterfalls-tour.a377450.activity-details)

![Portland: 2-hour Lunch Cruise on the Willamette River](https://mediaim.expedia.com/localexpert/4750997/c820f411-cf79-4db0-9f68-8b4665a90575.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Portland: 2-Hour Lunch Cruise Through Downtown

CA $121

per adult

**98%** of travellers recommend

[](https://expedia.ca/things-to-do/portland-2-hour-lunch-cruise-through-downtown.a4750997.activity-details)

![Full-Day Guided Oregon Coast Tour from Portland](https://mediaim.expedia.com/localexpert/4438108/fa7862af-8c2e-4832-b281-b60125b0267c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Full-Day Guided Oregon Coast Tour from Portland

CA $190

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/full-day-guided-oregon-coast-tour-from-portland.a4438108.activity-details)

[See all activities in Portland](https://expedia.ca/things-to-do/search?rid=553248635976386737)

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