Portland Trips (flight + hotel)

Photo by Matthew Jay

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to P 3,118 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

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

Top hotels in Portland

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 P7,326 per night from Aug 24 to Aug 25
P7,326
P8,279 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (923 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 P9,751 per night from Sep 1 to Sep 2
P9,751
P11,020 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"Beautiful property right on the water. Enjoyed lunch at the hotel restaurant"

Reviewed on Aug 5, 2025

Chautauqua Harbor Hotel - Jamestown
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 P9,293 per night from Aug 7 to Aug 8
P9,293
P10,501 total
Aug 7 - Aug 8
includes taxes & fees
7/10 Good! (152 reviews)
"Webb's Resort is a quaint accommodation. It's about 5 minutes away from the Chataqua Institute. It was perfect for our overnight stay after attending the Laufey concert at the Chataqua Institute. We had the lakeside view which was literally across the street from the lake. I'd definitely stay ..."

Reviewed on Aug 5, 2025

Webb's Year Round Resort
See all 473 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.