Portland Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Find the Best Portland Vacation Packages

Portland Hotel Deals

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country

Portland
The price is ￥30,582 per night from Sep 2 to Sep 3
￥30,582
￥52,755 total
Sep 2 - Sep 3
includes taxes & fees
10/10 Exceptional! (33 reviews)
"We loved it...even got to see eagles flying around while sitting on outside deck...beautiful sunsets and chairs to watch them from. Julie was available and very nice taking care of us."

Reviewed on Jul 31, 2025

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Clarion Hotel Conference Center on Lake Erie

Clarion Hotel Conference Center on Lake Erie

2.5 out of 5
30 Lake Shore Dr E, Dunkirk, NY
Fully refundableReserve now, pay when you stay
The price is ￥19,939 per night from Aug 17 to Aug 18
￥19,939
￥22,532 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (924 reviews)
"Our 2 night stay was very welcoming and the morning breakfast had a wonderful variety."

Reviewed on Jul 28, 2025

Clarion Hotel Conference Center on Lake Erie
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave, Celoron, NY
The price is ￥21,223 per night from Sep 1 to Sep 2
￥21,223
￥23,983 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Beautiful property right on the water. Enjoyed lunch at the hotel restaurant"

Reviewed on Aug 5, 2025

Chautauqua Harbor Hotel - Jamestown
See all 474 properties in Portland
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 Portland vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation to Portland costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
You can typically find lower prices and better availability in November, December and January. Check out our cheap Portland vacation packages and you could score some great off-season discounts.
How many days is enough for Portland?
With a well-organized travel plan, you can easily tick off the top Portland attractions in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Portland vacation for longer.
How to find the best Portland package deals?
Use Expedia's filters to find some fabulous Portland package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Portland package deals in the off-season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Portland vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally snag a better deal than booking each component individually. And you'll still get the freedom to create a customized Portland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Portland?
Land amazing discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for an impromptu Portland getaway.
How to plan a trip to Portland?

  1. Choose your travel dates: The things you'd like to do in Portland and your favorite season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will likely be the largest expense during your trip to Portland.
  3. Determine how many days away: Start by listing all the activities and attractions you want to experience in Portland. Then, estimate how long you'll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Portland vacation package.

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