Title: Hillside Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $516 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. ![Mark Spencer Hotel](https://images.trvl-media.com/lodging/1000000/20000/20000/19921/e8cf5bcf_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Mark Spencer Hotel Downtown Portland CA $516 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PDX) 9.2/10 Wonderful! (1,838 reviews) I don’t like how check in was at 4pm. Pretty inconvenient having to fly in and store our stuff in their storage. Also, one of the concierge men had an attitude as if we inconvenienced them when trying to get some stuff out of or stored luggage. We had to get ready in the lobby. Also, the cards they gave us had to be reactivated one night. Other than that it was ok. Reviewed on Dec 15, 2025 ![The Nines, a Luxury Collection Hotel, Portland](https://images.trvl-media.com/lodging/3000000/2150000/2140800/2140707/16ca0027_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Nines, a Luxury Collection Hotel, Portland Downtown Portland CA $723 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PDX) 9/10 Wonderful! (1,002 reviews) Amazing hotel with restaurants clean and quiet treated like royalty! Safe and beautiful amenities and decor Reviewed on Nov 5, 2025 ![Hotel Lucia](https://images.trvl-media.com/lodging/1000000/20000/16000/15988/b0d3e02c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Lucia Downtown Portland CA $546 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PDX) 9.2/10 Wonderful! (1,279 reviews) Need to upgrade the TVs in the room. They should be able to get to the internet for Netflix or Amazon. Reviewed on Dec 7, 2025 ![Kimpton Hotel Vintage Portland by IHG](https://images.trvl-media.com/lodging/1000000/10000/3000/2993/0d52504a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Hotel Vintage Portland by IHG Downtown Portland CA $594 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PDX) 9/10 Wonderful! (1,001 reviews) Walkable area, hotel was very well kept. Reviewed on Dec 1, 2025 ![Sentinel Hotel](https://images.trvl-media.com/lodging/1000000/10000/1900/1854/9a394282_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sentinel Hotel Downtown Portland CA $617 per person Feb 16 - Feb 20 found 1 day ago Roundtrip flight included Vancouver (YVR) to Portland (PDX) 8.8/10 Excellent! (1,005 reviews) The room was pristine. When I walked in, they had music on all the lights were up. It felt very calming. I was there for an event at Jake’s Grill… The food was underwhelming. The next morning I ordered room service and I was brought a different order than what I had ordered. So the hotel is amazing, but the restaurant is not. Reviewed on Dec 11, 2025 ## 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://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20823-Downtown-Portland.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/347000/347616-Alberta-Street.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Northeast Portland 2 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) ![Oregon Museum of Science and Industry](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20688-Oregon-Museum-Of-Science-And-Industry-Omsi.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/544000/544253-pearl-district-portland.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) ![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/20000/20852-Tom-Mccall-Waterfront-Park.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 ![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 $151 total Dec 21 - Dec 22 includes taxes & fees 9.2/10 Wonderful! (3,071 reviews) I love it- Great service Reviewed on Dec 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=330558&PinnedHotelID=330558&HadPinnedHotel=true®ionId=553248635976387058) ![DoubleTree by Hilton Hotel Portland](https://images.trvl-media.com/lodging/1000000/10000/9600/9555/74c5c04c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### DoubleTree by Hilton Hotel Portland 1000 NE Multnomah Street Portland OR Fully refundableReserve now, pay when you stay CA $151 CA $176 total Dec 25 - Dec 26 includes taxes & fees 8.2/10 Very Good! (1,006 reviews) Yes Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=25%2F12%2F2025&endDate=26%2F12%2F2025&selected=9555&PinnedHotelID=9555&HadPinnedHotel=true®ionId=553248635976387058) ![Embassy Suites by Hilton Portland Downtown](https://images.trvl-media.com/lodging/1000000/80000/74700/74615/d07bd195_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Embassy Suites by Hilton Portland Downtown 319 SW Pine St Portland OR Fully refundableReserve now, pay when you stay CA $139 CA $164 total Jan 7 - Jan 8, 2026 includes taxes & fees 8.6/10 Excellent! (1,332 reviews) The room was gorgeous!The staff was kind. I love the drinks and snacks in the evenings and the Christmas tree was beautiful. They also have a valet for a small price. The pool is a beautiful salt water pool and the hot tub was wonderful as well. I will definitely book a room here again. Reviewed on Dec 8, 2025 [](https://expedia.ca/Hotel-Search?startDate=07%2F01%2F2026&endDate=08%2F01%2F2026&selected=74615&PinnedHotelID=74615&HadPinnedHotel=true®ionId=553248635976387058) [See all 2,843 properties in Hillside](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=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? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.