Title: Hillside Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $776 Expedia.ca

[Hotels in Hillside](https://expedia.ca/Hillside-Portland-Hotels.0-n553248635976387058-0.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)[Hillside Car Rentals](https://expedia.ca/Car-Rentals-In-Hillside.d553248635976387058.Car-Rental-Guide)

![](https://images.trvl-media.com/place/2759/923e5abf-c8eb-403b-b112-9db7e2b3b34b.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Hillside Vacation Packages

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

Photo by BDM Traveling

- ##  
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 Hillside Vacation

The easiest way to experience this unique city is with a customized Hillside vacation package. Stay in the neighborhood of Overlook, which is good for cycling, bars and pubs and dining or choose someplace else — our packages are all about you. Eager to explore your new surroundings? [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 just a few of the top places to visit during your trip to Hillside. Whatever your travel plans or budget, putting together the ultimate tailored Hillside vacation is simple with Expedia.

## Top Holiday Package Deals in Hillside

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

![SCP Depoe Bay](https://images.trvl-media.com/lodging/47000000/46510000/46506600/46506596/19b5a7f6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SCP Depoe Bay

CA $776

per person

May 19 - May 24

found 15 hours ago

Roundtrip non-stop flight included

Edmonton (YEG) to Portland (PDX)

9.2/10 Wonderful! (574 reviews)

Nice, smaller property overlooking the bay. Nothing too fancy, and it it is good to know that there is no staff available in the evening, however overall it was a nice stay..

Reviewed on Feb 22, 2026

![Bowline Hotel](https://images.trvl-media.com/lodging/69000000/68170000/68168900/68168810/f6d90933_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Bowline Hotel

CA $1,118

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

9.4/10 Exceptional! (1,002 reviews)

Wonderful room and staff.

Reviewed on Feb 23, 2026

![Two Capes Lookout](https://images.trvl-media.com/lodging/110000000/109920000/109914100/109914073/0b7eccb4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Two Capes Lookout

CA $1,066

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

9.8/10 Exceptional! (85 reviews)

Our overall experience was incredible. Upon arrival, the staff was very welcoming, informative, and helpful. Our room was perfect. The view of the ocean was beautiful, the bed was the coziest bed I’ve ever slept in, and the little details throughout were so thoughtful. I wish we could have stayed there longer and we will absolutely be making a trip back as soon as possible.

Reviewed on Dec 29, 2025

![The Tillamook Inn](https://images.trvl-media.com/lodging/1000000/20000/15900/15856/a3451dc7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Tillamook Inn

CA $781

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

8/10 Very Good! (1,081 reviews)

Clean room and very convenient for our trip. New remodel is finally finished so looking good.

Reviewed on Feb 21, 2026

![Hi-Tide Oceanfront Inn](https://images.trvl-media.com/lodging/6000000/5500000/5494400/5494356/09c304f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hi-Tide Oceanfront Inn

CA $912

per person

Apr 3 - Apr 8

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Portland (PDX)

9/10 Wonderful! (1,724 reviews)

Room was decent size and clean. The battery on the card key needed replacement. My daughter had a problem with it earlier in the evening and thought is was just an operational error but found myself unable to get back in the room at 2 am after taking my dog out.

Reviewed on Feb 23, 2026

## Where to stay in Hillside

Find the best Hillside areas and neighborhoods for the activities you enjoy most. [Learn more about Hillside](https://expedia.ca/Portland-Hillside.dx553248635976387058)

![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

 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)

## Hillside Hotel Deals

![Park Lane Suites and Inn](https://images.trvl-media.com/lodging/1000000/30000/26100/26052/cb7e437c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Park Lane Suites and Inn

809 SW King Avenue Portland OR

Fully refundable

CA $104

CA $121 total

Mar 9 - Mar 10

includes taxes & fees

8.8/10 Excellent! (1,643 reviews)

Clean, comfortable, nice lobby, free parking

Reviewed on Feb 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=26052&PinnedHotelID=26052&HadPinnedHotel=true&regionId=553248635976387058)

![The Paramount Hotel](https://images.trvl-media.com/lodging/1000000/340000/330600/330558/b2e58e4b_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

The Paramount Hotel

808 SW Taylor St Portland OR

Fully refundableReserve now, pay when you stay

CA $129

CA $150 total

Mar 1 - Mar 2

includes taxes & fees

9.2/10 Wonderful! (3,219 reviews)

Great stay in DT Portland!

Reviewed on Feb 26, 2026

[](https://expedia.ca/Hotel-Search?startDate=01%2F03%2F2026&endDate=02%2F03%2F2026&selected=330558&PinnedHotelID=330558&HadPinnedHotel=true&regionId=553248635976387058)

![Radisson Hotel Portland Airport](https://images.trvl-media.com/lodging/1000000/50000/40700/40663/6c6ccb81_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Radisson Hotel Portland Airport

6233 NE 78th Court Portland OR

Fully refundable

CA $133

CA $161 total

Mar 10 - Mar 11

includes taxes & fees

9/10 Wonderful! (2,980 reviews)

The room was clean and comfortable and the staff was friendly and accommodating.

Reviewed on Feb 24, 2026

[](https://expedia.ca/Hotel-Search?startDate=10%2F03%2F2026&endDate=11%2F03%2F2026&selected=40663&PinnedHotelID=40663&HadPinnedHotel=true&regionId=553248635976387058)

[See all 2,872 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F02%2F2026&endDate=28%2F02%2F2026&regionId=553248635976387058)

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 a Hillside vacation package cost?

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

### Where should I stay in Hillside?

### What are the top hotels in Hillside?

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

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

### What should I know before booking a Hillside travel package?

### Can I choose my airline with a Hillside Expedia vacation package?

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

### Discover the most popular places to visit in Hillside

![Pittock Mansion which includes a park, a house and heritage architecture](https://images.trvl-media.com/place/502353/121f30dd-ed10-4728-acc1-7ebebf46c06c.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Pittock Mansion

A wonderfully preserved example of life in a bygone era and spectacular views await at one of America’s finest stately homes.

[](https://expedia.ca/Pittock-Mansion-Northwest-Portland.d502353.Vacation-Attraction)

![Moda Center](https://images.trvl-media.com/place/6295463/a89d989a-fbfa-4a0c-b687-603ed6e6fd73.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Moda Center

See sporting teams do battle and rock out to musical legends at one of Portland’s major venues for sports and big-ticket entertainment events.

[](https://expedia.ca/Moda-Center-North-Portland.d6295463.Vacation-Attraction)

![Oregon Zoo showing landscape views and zoo animals as well as a large group of people](https://images.trvl-media.com/place/502371/f410e897-19a4-4f39-89ae-326d42afdeaf.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Oregon Zoo

Awesome beasts native to America have a home alongside exotic and endangered species from around the world at this picturesque Portland attraction.

[](https://expedia.ca/Oregon-Zoo-Southwest-Portland.d502371.Vacation-Attraction)

### Things to do

![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)

![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)

![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=553248635976387058)

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