Portland Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Jay
    deals illustration
    Better together
    Save up to ฿4,531 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

Top hotels in Portland

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 ฿7,432 per night from 8 Jul to 9 Jul
฿7,432
฿8,398 total
8 Jul - 9 Jul
includes taxes & fees
9.6/10 Exceptional! (1,000 reviews)
"There was a slight issue at check in but was fixed. The room was clean and beautiful, the location is amazing. Great food, drinks and staff is very accommodating"

Reviewed on 24 Jun 2025

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 ฿4,269 per night from 13 Jul to 14 Jul
฿4,269
฿4,824 total
13 Jul - 14 Jul
includes taxes & fees
7.6/10 Good! (897 reviews)
Dunkirk, way more than we expected!
"Edgar was extrememly helpful! A huge thanks to Edgar! Nadia was also extrememly helpful when doing the or booking, originally had a mistake, but she was able to fix the issue and make the trip easy! Thanks to all the great staff at this location!"

Reviewed on 24 Jun 2025

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 ฿5,271 per night from 30 Jun to 1 Jul
฿5,271
฿5,957 total
30 Jun - 1 Jul
includes taxes & fees
7/10 Good! (117 reviews)
"I really liked having the outdoor patio, jacuzzi, small refrigerator, coffee maker, & microwave in the room. The bed was nice and comfortable. I liked the workout room, downstairs pool and jacuzzi. However, the two eliptical machines didn't work for tracking, but I used my fit bit and still enjoyed ..."

Reviewed on 23 Jun 2025

Webb's Year Round Resort
See all 478 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 holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages and you could score some great off-season discounts.
How many days is enough for Portland?
With a well-organised 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 holiday 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 holiday package as early as possible.
Is it cheaper to book a Portland holiday as a package?
Expedia holiday 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 customised Portland holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 favourite 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 personalised Portland holiday package.

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