Happy Valley Vacation Packages
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Your Happy Valley Vacation
Lock in a Happy Valley vacation package that includes everything you need without any unnecessary extras. Good for shopping, nightlife and bars and pubs, think about staying in the neighborhood of Mississippi District. If your trip to Happy Valley includes some sightseeing, hit up much-loved attractions like Clackamas Town Center, Reed College and Mall 205. Expedia is here to help you escape the everyday. Tailor your vacation to Happy Valley to suit your travel style, whatever that may be.
Top Happy Valley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Inn of the White Salmon
CA $773
per person
Oct 26 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Portland (PDX)
9.4/10 Exceptional! (113 reviews)
Very small, quiet room, tiny bath, nice shower, bed ok but too soft for me, awkward bedside lamp switches, lovely, very quiet, outdoor lounge/garden areas, really cute quiet, friendly town. Price was right.
Reviewed on Sep 18, 2026
Darlingwood
CA $902
per person
Nov 5 - Nov 8
found 14 hours ago
Roundtrip non-stop flight included
Detroit (DTT) 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 Aug 10, 2026
Ready to book your vacation to Happy Valley?
Happy Valley Hotel Deals
Heathman Hotel
1001 SW Broadway Portland OR
Fully refundableReserve now, pay when you stay
CA $142
CA $213 total
Oct 18 - Oct 19
includes taxes & fees
9.2/10 Wonderful! (1,084 reviews)
"Excellent location, and wonderful vibe."
Reviewed on Sep 25, 2026
The Paramount Hotel
808 SW Taylor St Portland OR
Fully refundableReserve now, pay when you stay
CA $167
CA $194 total
Oct 14 - Oct 15
includes taxes & fees
9.2/10 Wonderful! (3,720 reviews)
"The room was tidy and bright. We had an issue with the mini-fridge not working and they replaced it as soon as we called the front desk about it. They were very attentive!"
Reviewed on Sep 26, 2026
Country Inn & Suites by Radisson, Portland International Airport, OR
7025 NE Alderwood Rd Portland OR
Fully refundable
CA $143
CA $167 total
Oct 27 - Oct 28
includes taxes & fees
8.8/10 Excellent! (3,253 reviews)
"This place was a dump. Save your money and go elsewhere."
Reviewed on Sep 25, 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.
Stay near popular Happy Valley attractions
Clackamas Town Center
8.6/10 (653 reviews)
During your trip to Happy Valley, you can find the perfect gifts to bring home at Clackamas Town Center. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Eagle Landing Golf Course
8.0/10 (1 review)
Play a round of golf in Happy Valley at Eagle Landing Golf Course, and enjoy other activities such as biking. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.
Hood View Park
7.6/10 (37 reviews)
Hood View Park is just one of the places to see in Clackamas, so why not enjoy the other things to explore during your travels? Discover the beautiful waterfalls in this walkable area, or enjoy its biking trails.
Park Mountain Lane Trailhead
7.4/10 (22 reviews)
You can take time to visit Park Mountain Lane Trailhead during your travels to Clackamas. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Sunnyside Road Trailhead
7.0/10 (13 reviews)
You can take time to visit Sunnyside Road Trailhead during your travels to Clackamas. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Cinemark Clackamas Town Center
You can take time to visit Cinemark Clackamas Town Center during your travels to Happy Valley.
Talbert Drive Trailhead
9.0/10 (4 reviews)
You can take time to visit Talbert Drive Trailhead during your travels to Clackamas. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
Cedar Park Trailhead
7.2/10 (20 reviews)
You can take time to visit Cedar Park Trailhead during your travels to Clackamas. Visit the shops in this family-friendly area, or simply enjoy its restaurants.
What to do in Happy Valley
Half-Day Multnomah Falls & Gorge Waterfalls Tour
CA $119
per traveller
96% of travellers recommend
Portland: 2-Hour Lunch Cruise Through Downtown
CA $123
per adult
98% of travellers recommend
Full-Day Mount Hood & Multnomah Falls Tour
CA $196
per traveller
96% of travellers recommend
Frequently asked questions
How much does a Happy Valley vacation package cost?
You can snap up a vacation package to this popular destination from CA $688 on Expedia. But how much your vacation to Happy Valley costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Happy Valley?
If you're hoping to score a cheap Happy Valley vacation package, consider visiting in January, May and October. You'll generally find lower rates on accommodations and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Happy Valley?
Happy Valley vacations can be short or long, but to get a true feel for this place, we reckon 4 days is about right. In this timeframe, you can fit in top attractions like Waverley Country Club and Eastmoreland Golf Course and seek out some underrated gems. Don't forget to explore neighbourhoods such as Sunnyside and Southgate either. If you're smart with your time, you can even schedule a day trip from Happy Valley too.
Is it worth booking a vacation package to Happy Valley?
It's no wonder a Happy Valley vacation is on the must-do list of many travellers. Well-known attractions like Hood View Park are just the start of what you can explore here.
How to find the best Happy Valley package deals?
Landing a cheap Happy Valley package deal is easy with Expedia. Once you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can tweak your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most wallet-friendly Happy Valley package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Happy Valley vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging hotels and flights separately. Better still, you can tailor your Happy Valley trip to match your exact needs. Choose your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Happy Valley?
If you have your Happy Valley travel dates finalized, book early to snap up some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are perfect for jetting off on a whim.
How to plan a trip to Happy Valley?
- Choose the right time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Happy Valley.
- Work out your budget: Ensure you have enough money to pay for everything from dining out and transportation to airfares and activities. Your accommodations will likely be the largest expense during your trip to Happy Valley.
- Decide your trip length: Consider how much time you want to spend discovering Happy Valley. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
- Combine your accommodations and airfare: Once you've settled on your dates and duration, book the ideal Happy Valley vacation package for you.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
