Hillsdale Vacation Packages

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Top Holiday Package Deals in Hillsdale

Price found within the past 48 hours. Click for updated prices.
Clackamas Inn & Suites

Clackamas Inn & Suites

2.5 out of 5
Price was CA $800, price is now CA $633 per person
CA $633
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PDX)
7.6/10 Good! (1,001 reviews)
Good parking and access most times- a bit close to the lights but can U turn in the shopping centre when travelling south.

Reviewed on Apr 30, 2026

Hampton Inn & Suites Portland-Pearl District

Hampton Inn & Suites Portland-Pearl District

3.5 out of 5
Pearl District
Price was CA $1,251, price is now CA $963 per person
CA $963
per person
Jun 30 - Jul 5
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PDX)
9.6/10 Exceptional! (2,146 reviews)
Great rooms, safe, quiet, great restaurant pool n fitness room free breakfast was really good

Reviewed on May 5, 2026

Hilton Vancouver Washington

Hilton Vancouver Washington

3.5 out of 5
Downtown Vancouver
Price was CA $1,733, price is now CA $1,369 per person
CA $1,369
per person
Jun 25 - Jun 30
found 20 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Portland (PDX)
9/10 Wonderful! (1,001 reviews)
Checked in at four and left the hotel around five and when we got back our room had been cleaned again and the door was left open n unlocked we had a great stay wouldn’t recommend leaving important things while gone tho

Reviewed on Apr 28, 2026

Dossier Hotel

Dossier Hotel

4.5 out of 5
Downtown Portland
Price was CA $931, price is now CA $747 per person
CA $747
per person
Jul 14 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Portland (PDX)
9.4/10 Exceptional! (1,399 reviews)
The front desk staff was nice and friendly. The location is also good. There was some construction going on nearby but overall nothing was disruptive. The part I dislike the most about the hotel is the cleanliness. The bed mattress was dirty with hair and stains. Disappointing.

Reviewed on May 6, 2026

Where to stay in Hillsdale

Find the best Hillsdale areas and neighborhoods for the activities you enjoy most. Learn more about Hillsdale
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

Hillsdale 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 $133 per night from May 25 to May 26
CA $133
CA $155 total
May 25 - May 26
includes taxes & fees
9.2/10 Wonderful! (3,367 reviews)
The staff was phenomenal and the property was very clean and modern. Definitely would book again.

Reviewed on May 6, 2026

The Paramount Hotel
DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
1000 NE Multnomah Street Portland OR
Fully refundableReserve now, pay when you stay
The price is CA $172 per night from May 24 to May 25
CA $172
CA $201 total
May 24 - May 25
includes taxes & fees
8.6/10 Excellent! (1,052 reviews)
clean room

Reviewed on May 4, 2026

DoubleTree by Hilton Hotel Portland
Country Inn & Suites by Radisson, Portland International Airport, OR

Country Inn & Suites by Radisson, Portland International Airport, OR

3 out of 5
7025 NE Alderwood Rd Portland OR
Fully refundable
The price is CA $143 per night from May 20 to May 21
CA $143
CA $167 total
May 20 - May 21
includes taxes & fees
8.8/10 Excellent! (2,811 reviews)
Manager was a tool

Reviewed on May 6, 2026

Country Inn & Suites by Radisson, Portland International Airport, OR
See all 2,901 properties in Hillsdale
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
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Frequently asked questions

How much does a Hillsdale vacation package cost?
Handcraft your Hillsdale vacation package from an affordable CA $633. Choose from any combination of hotels, flights and rental cars to put together the escape you've been dreaming about for ages. Don't forget to add on one or two experiences!
How do I get a cheap travel package to Hillsdale?
If you love landing a bargain, combine your bookings into a Hillsdale vacation package. Whether you need flights, hotels, day tours or rental cars, you can browse and book them all in one place. You'll have plenty of choice at your fingertips too. Expedia has over 550 airlines and 1,000,000 properties worldwide to take your pick of. Fly with who you prefer, find a room where you like and save precious dollars — now that's the perfect getaway!
Where should I stay in Hillsdale?
Most who travel to Hillsdale include Oregon Zoo and Portland State University on their itineraries. Why not go for a hotel that's close to these great attractions?
How far in advance should I book my Hillsdale vacation?
While not all air carriers release ticket prices early, customers are usually able to compare international fares on Expedia up to 12 months in advance. This is the time you'll score some fantastic bargains. If you're booking last minute, you may still be in luck. Sometimes the cheapest prices emerge only weeks prior to departure.
What does an Expedia Hillsdale travel package include?
Hotels, rental cars and flights, or any combination of the three — the choice is yours. Whether you're headed to Hillsdale with the kids or enjoying a solo break, there's a bundle to match every style and budget. Once you've made your booking, why not add on a couple of activities?
What should I know before booking a Hillsdale travel package?
A travel package can be easier on the wallet than individually booking everything you need for your escape. For example, bundle your hotels, flights and rental cars and score big savings. Whatever your vacation plans, you'll find a package that's right for you.
Can I choose my airline with a Hillsdale Expedia vacation package?
Expedia offers access to more than 550 airline partners worldwide, so you sure can! Simply pick the carrier that suits you and craft your ideal Hillsdale vacation.
If I'm not able to travel, can I cancel my Hillsdale vacation package?
Don't stress if you're rethinking your Hillsdale vacation package — it's possible to cancel or amend your booking. And if you've booked it within 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally understand your circumstances can suddenly change, so head to our Customer Service Portal if that occurs. When you're ready to make changes, we're here to help.

Discover the most popular places to visit in Hillsdale

Oregon Zoo

Oregon Zoo

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

Oregon Zoo
Moda Center

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.

Moda Center
Tom McCall Waterfront Park

Tom McCall Waterfront Park

Cool off in the fountain, walk or bike the paths, or take in a festival at the Tom McCall Waterfront Park.

Tom McCall Waterfront Park

Things to do

Portland: 2-hour Lunch Cruise on the Willamette River

Portland: 2-Hour Lunch Cruise Through Downtown

CA $123
per adult
98% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
Full-Day Guided Oregon Coast Tour from Portland

Full-Day Guided Oregon Coast Tour from Portland

CA $192
per adult
100% of travellers recommend
Full-Day Guided Oregon Coast Tour from Portland
Portland: Willamette River 2.5-hour Dinner Cruise

Portland: Dinner Cruise on the Willamette River

CA $178
per adult
96% of travellers recommend
Portland: Dinner Cruise on the Willamette River
See all activities in Portland
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.