Portland Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Jay
    deals illustration

    Better together

    Save up to NT$5,067 when you book a flight and hotel together*
    stays illustration

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration

    Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Portland Vacation Packages

Portland Hotel Deals

Chautauqua Harbor Hotel - Jamestown
Chautauqua Harbor Hotel - Jamestown
3.5 out of 5
10 Dunham Ave, Celoron, NY
Fully refundableReserve now, pay when you stay
The price is NT$6,420 per night from Jul 23 to Jul 24
NT$6,420
NT$7,255 total
Jul 23 - Jul 24
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Caught some great sunsets over/on the lake. Seaweed, but it really didn’t impact our stay much"

Reviewed on 2025/7/9

Chautauqua Harbor Hotel - Jamestown
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 NT$3,934 per night from Aug 10 to Aug 11
NT$3,934
NT$4,446 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (908 reviews)
"Beautiful location right on the Lake. Wonderful room and breakfast!"

Reviewed on 2025/7/3

Clarion Hotel Conference Center on Lake Erie
Webb's Year Round Resort
Webb's Year Round Resort
2.5 out of 5
125 W Lake Rd, Mayville, NY
Fully refundableReserve now, pay when you stay
The price is NT$4,704 per night from Jul 16 to Jul 17
NT$4,704
NT$5,316 total
Jul 16 - Jul 17
includes taxes & fees
7/10 Good! (125 reviews)
Nice facility
"Only negative is that the breakfast left something to be desired. They need a kitchen and staff to manage and maintain the breakfast area…"

Reviewed on 2025/7/9

Webb's Year Round Resort
See all 476 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.