Hillsdale Holidays from £2,757
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Your Hillsdale Holiday
Organising your next getaway just got a whole lot easier with a holiday package to Hillsdale. Experience the best this neighbourhood has to offer while creating nice memories that'll stay with you for years. Can't wait to head out and see the sights during your trip to Hillsdale? Be sure to check out nearby attractions like Oregon Zoo, Portland State University and Portland Japanese Garden. Whatever your ideal Hillsdale holiday may look like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
The Dundee - A Trace Hotel
£2,823
per person
22 Oct - 27 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Portland (PDX)
10/10 Exceptional! (52 reviews)
Comfortable and generously sized room. Check-in was easy, room was quiet, comfortable and dark enough to sleep easily. Staff helpful. Breakfast options limited, but good enough and coffee was great. My only complaint is being awakened during one of the best night’s sleep I’ve had in months, by the alarm clock that I did not set. Someone had apparently previously set it to 6:01AM and it woke me out of a deep sleep. I couldn’t find a way to shut it off, finally unplugged it and it kept going on battery power. My heart was racing at that point and it was impossible to get back to sleep. Perhaps the housekeeping checklist could include making sure the alarm clock is turned off. I can’t imagine that most guests would think to check it unless they are setting an alarm for themselves. For me, alarm clocks are unnecessary because if I need an alarm, I use my phone.
Reviewed on 29 Aug 2026
Darlingwood
£2,819
per person
22 Oct - 27 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Portland (PDX)
9.6/10 Exceptional! (4 reviews)
The setting is tranquil, with beautiful views, and the home itself is lovely. Our host was welcoming and gracious. The B&B is about two miles down gravel roads with fairly deep washboards, so guests should be prepared for a rough drive.
We love staying at true bed and breakfasts, and for us, part of the charm is the experience of a thoughtfully prepared, homemade breakfast. Unfortunately, the breakfast we received was a bit disappointing—a scone, two strawberries, and five blueberries left us wanting more.
In fairness, the fault is partly ours for not having more realistic expectations about what was included. The property and setting are beautiful, and the host was very welcoming, but the breakfast experience did not live up to what we typically expect from a bed and breakfast.
Reviewed on 10 Aug 2026
Youngberg Hill
£3,178
per person
22 Oct - 27 Oct
found 1 day ago
Return flight included
Dublin (DUB) to Portland (PDX)
9.4/10 Exceptional! (104 reviews)
I loved my stay here. The room was spectacular from the panoramic views to the details of the room decor makes this vineyard a magical place to unwind from the day to day grind. Highest recommendation to the staff who were so friendly. The wine tasting room and outdoor decks are fantastic as well. Relaxing with a glass of wine e was so peaceful.
Reviewed on 19 Aug 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
2 out of top 10 points of interest in this area
Make time to explore the heart of the city and discover great food, shopping and entertainment.
Northeast Portland
1 out of top 10 points of interest in this area
While you're in Northeast Portland, take in top sights like Moda Center or The Grotto, and hop on the metro to see more of the city at Parkrose-Sumner Transit Center or NE 82nd Avenue Station.
Pearl District
Stay in a hotel here as a base to enjoy this fascinating neighborhood’s offerings, from morning coffee to late-night arts.
Southeast Portland
Travellers choose Southeast Portland for its ample dining options. Hop aboard the metro at SE Powell Boulevard Station or SE Holgate Boulevard Station and check out top sights like Mall 205.
Southwest Portland
3 out of top 10 points of interest in this area
Southwest Portland is highly notable for its stunning river views, and you might want to visit top sights like Oregon Zoo and Terwilliger Boulevard Parkway. See more of Portland by jumping on the metro at Bancroft St Stop or S Lowell & Bond Stop.
Top hotels in Hillsdale
The Paramount Hotel
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
£96
30 Aug - 31 Aug
includes taxes & fees
Oxford Suites Portland - Jantzen Beach
12226 N JANTZEN DRIVE Portland OR
Fully refundableReserve now, pay when you stay
£88
3 Sept - 4 Sept
includes taxes & fees
Hyatt Regency Portland at the Oregon Convention Center
375 NE Holladay St Portland OR
Fully refundableReserve now, pay when you stay
£129
20 Sept - 21 Sept
includes taxes & fees
9.4/10 Exceptional! (1,795 reviews)
"It is a great location if you have a conference or event at the convention center. If you don't - check the convention center schedule! We arrived on a concert night - no parking and a 20 minute wait for one of 6-8 elevators. It was crazy. Loud hallways. Not restful. Sorry."
Reviewed on 29 Aug 2026
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.
Frequently asked questions
How much does a Hillsdale travel package cost?
Much less than you might think — from just £2,757, in fact! By combining flights, hotels and car rentals into a custom-built package, your Hillsdale escape is just clicks away.
If I'm not able to travel, can I cancel my Hillsdale travel package?
Plans can change suddenly, so yes. You may be able to cancel or alter your Hillsdale travel package for free if you've booked in the last 24 hours. For bookings older than that, you can still make changes, but your airline, hotel or car rental company may impose a charge. Want more information? Take a look at our Customer Service Portal. We'll help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to Hillsdale?
Track down flights that fit your schedule, add a hotel to your booking and watch how much you save with a Hillsdale travel package. It's as easy as that! From hotels and flights to rental cars and tours, Expedia is where your cheap holiday begins. And with over 550 air carriers and 1,000,000 properties around the world to choose from, you'll never be short of choice.
Does Expedia offer Book Now, Pay Later Hillsdale holidays?
Your bank balance shouldn't stop you from escaping on holiday, so Expedia has worked out a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book your dream getaway without using up all your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:
- Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If paying a little each month works for you, choose this option at checkout.
- Pay in instalments holidays: Into the idea of paying for your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
- Low deposit holidays: When you want to jump on an amazing deal but your budget doesn't quite go that far, Klarna's low deposit holiday plan will help you secure your getaway.
Where should I stay in Hillsdale?
Urban explorers come from all over the world to see Oregon Zoo and Portland State University in Hillsdale. Book a room within a stone's throw of these must-see attractions and visit them whenever you want.
What are the top hotels in Hillsdale?
Book a room at DoubleTree by Hilton Hotel Portland. It's one of the area's most sought-after properties. Another highly rated option in Hillsdale is Park Lane Suites and Inn.
How far in advance should I book my Hillsdale holiday?
It all depends on the airline, but you can generally compare international flights on Expedia up to 12 months in advance. While it's generally a good idea to book ahead of time, lucky customers occasionally find a cheaper ticket just weeks prior to their intended journey.
What does an Expedia Hillsdale travel package include?
Flights, hotels and rental cars, or any combination of them — you decide! Whether you're venturing to Hillsdale with the entire family or adventuring with your friends, there's a package to fit every budget and style. Once you've made your booking, why not add on a couple of tours or activities?
What should I know before booking a Hillsdale travel package?
Booking all the parts of your escape together is a simple way to save. Bundle your flights, car rentals and hotels into a neat little package. But it's not just hotels. Expedia has all types of properties, including holiday rentals such as beachside villas and city residences. Your choices are almost endless!
Can I choose my airline with a Hillsdale Expedia travel package?
You sure can. We offer more than 550 partner airlines all over the world, so go with the carrier that fits your budget and travelling style.
Stay near popular Hillsdale attractions
Stephens Creek Natural Area
Explore the lovely green spaces of Stephens Creek Natural Area and also enjoy the cycling trails in Portland. Wander the riverfront and picturesque gardens in the area.
Hillsdale City Park
After visiting Hillsdale City Park, make a plan to see the other sights and activities in Portland. Make time to visit the area's shops or simply enjoy its top-notch restaurants.
Stephens Creek Natural Park
Explore the lovely green spaces of Stephens Creek Natural Park and also enjoy the cycling trails in Portland. Wander the riverfront and picturesque gardens in the area.
George Himes Park
George Himes Park is just one of the places to see in Portland, so why not enjoy the other things to explore during your travels? Experience the area's acclaimed art galleries and entertainment choices.
Dewitt City Park
After visiting Dewitt City Park, make a plan to see the other sights and activities in Portland. Discover the area's acclaimed art galleries and shops.
Gray Park
Explore the lovely green spaces of Gray Park and also enjoy the cycling trails in Portland. Make time to visit the area's shops or simply enjoy its top-notch restaurants.
DeWitt Park
Explore the lovely green spaces of DeWitt Park and also enjoy the cycling trails in Portland. Wander around the area's picturesque gardens or experience its entertainment choices.
Things to do
Half-Day Multnomah Falls & Gorge Waterfalls Tour
£62
per traveller
96% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
£65
per adult
98% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
£103
per traveller
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.