Portland Vacations from $463
Book a Hotel + Flight or Car together to unlock savings
Your Portland Vacation
The vibrant city of Portland is calling your name. Discover its hot spots and hidden treasures with a Portland vacation package that's tailored to you. A trip to Portland is an ideal opportunity to do a bit of sightseeing. Be sure to look around popular attractions like Lake Erie State Park, Vetter Vineyards Winery and Hillview Golf Course. That dream Portland vacation is just clicks away. Search flights, hotels and more on Expedia for an adventure that's tailored to suit your travel style.
The Latest Portland vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Jamestown by IHG
$463
per person
Nov 6 - Nov 10
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Jamestown (JHW)
9/10 Wonderful! (863 reviews)
We stay at this location every time we bring our kid to college. It’s become a home away from home. The staff are all always super helpful and so nice. The rooms are great and spacious. Coffee and breakfast downstairs are really good.
My only qualm is the walls are on the thinner side so having neighbors who are noisier can be a pain but we live. I have literally zero complaints about the hotel itself.
Reviewed on Oct 3, 2026
Webb's Year Round Resort
$492
per person
Nov 6 - Nov 10
found 20 hours ago
Roundtrip flight included
Tampa (TPA) to Jamestown (JHW)
6.6/10 (334 reviews)
#1 Hotels.com booked us into a booked hotel.
#2 The staff tried to find us a room.
#3 Said room was still dirty because it was already rented, but whomever was in the room moved for us.
#4 Room had a 30 pack of empty Bud Light cans and small piles of swept garbage.
#5 Beds were not made with clean linens
It was a disaster caused by Hotels.com
Reviewed on Oct 5, 2026
Stay near popular Portland attractions
21 Brix Winery
You can enjoy a tasting or tour at 21 Brix Winery during your travels to Portland.
Portland Hotel Deals
Clarion Hotel Conference Center on Lake Erie
30 Lake Shore Dr E Dunkirk NY
Fully refundable
$101 nightly
$114 total
Nov 1 - Nov 2
Total with taxes and fees
7.6/10 Good! (1,006 reviews)
"it wa ok"
Reviewed on Oct 6, 2026
Chautauqua Harbor Hotel - Jamestown
10 Dunham Ave Celoron NY
Fully refundableReserve now, pay when you stay
$135 nightly
$153 total
Nov 1 - Nov 2
Total with taxes and fees
Webb's Year Round Resort
125 W Lake Rd Mayville NY
Fully refundableReserve now, pay when you stay
$119 nightly
$134 total
Oct 7 - Oct 8
Total with taxes and fees
6.6/10 (338 reviews)
"#1 Hotels.com booked us into a booked hotel. #2 The staff tried to find us a room. #3 Said room was still dirty because it was already rented, but whomever was in the room moved for us. #4 Room had a 30 pack of empty Bud Light cans and small piles of swept garbage. #5 Beds were not made with clean ..."
Reviewed on Oct 5, 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.
Find the Best Portland Vacation Packages
Portland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 4,700 |
Top Sights | Lake Erie State Park, Dunkirk Historical Museum and Johnson Estate Winery |
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Frequently asked questions
How much does a Portland vacation package cost?
Offering excellent value package deals from $463 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?
The ideal length of your Portland vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to hit all the leading attractions and discover some hidden spots along the way.
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.
Does Expedia offer Book Now, Pay Later Portland vacation packages?
If you're like us, you love jet-setting around the world but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Portland break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.