Portland Vacations from $433

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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.
Clarion Pointe Jamestown - Falconer

Clarion Pointe Jamestown - Falconer

2.5 out of 5
Price was $448, price is now $433 per person
$433
per person
Mar 6 - Mar 7
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Jamestown (JHW)
8/10 Very Good! (976 reviews)
If you are going to advertise a hot breakfast bar photos, you need to provide it.I was very disappointed. Not worth the money

Reviewed on Nov 3, 2025

La Quinta Inn & Suites by Wyndham Jamestown

La Quinta Inn & Suites by Wyndham Jamestown

3 out of 5
Price was $640, price is now $626 per person
$626
per person
Mar 12 - Mar 14
found 11 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Jamestown (JHW)
8.4/10 Very Good! (1,000 reviews)
Clean room, good breakfast. Staff was nice.

Reviewed on Jan 5, 2026

Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
Price was $469, price is now $451 per person
$451
per person
Mar 6 - Mar 7
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Jamestown (JHW)
7.2/10 Good! (198 reviews)
Was great...real relaxing...and hosting was great...they were more then willing to help with all..AAA+++

Reviewed on Nov 23, 2025

The Spencer Hotel & Spa

The Spencer Hotel & Spa

2.5 out of 5
Price was $529, price is now $511 per person
$511
per person
Mar 6 - Mar 7
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Jamestown (JHW)
8/10 Very Good! (16 reviews)
This is a historic property. It was quaint, quiet, and clean. We were made to feel very welcome. It was so fun to walk around and see all the homes and amenities in the Chautauqua Institute.

Reviewed on Sep 23, 2025

Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
Price was $455, price is now $450 per person
$450
per person
Mar 6 - Mar 7
found 11 hours ago
Roundtrip flight included
Dallas (DFW) to Jamestown (JHW)
9.2/10 Wonderful! (787 reviews)
They had bacon for breakfast.

Reviewed on Jan 1, 2026

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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 NY
$297 nightly
The price is $336 total per night from Feb 1 to Feb 2
$336 total
Feb 1 - Feb 2
Total with taxes and fees
10/10 Exceptional! (52 reviews)
thanks julie & will be back again!

Reviewed on Jan 1, 2026

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
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
$110 nightly
The price is $124 total per night from Feb 2 to Feb 3
$124 total
Feb 2 - Feb 3
Total with taxes and fees
9.6/10 Exceptional! (1,000 reviews)
Room was very clean. Spacious. Comfortable. Kind and polite staff. Not a lot of available snacks so bring your own. Breakfast is a tad pricey but pretty good. Did not have any other meals.

Reviewed on Jan 28, 2026

Chautauqua Harbor Hotel - Jamestown
Quality Inn Dunkirk

Quality Inn Dunkirk

2.5 out of 5
3925 Vineyard Dr Dunkirk NY
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $119 total per night from Mar 1 to Mar 2
$119 total
Mar 1 - Mar 2
Total with taxes and fees
7.6/10 Good! (520 reviews)
Pet friendly. Easy parking. Clean room. Breakfast could be improved greatly.

Reviewed on Jan 8, 2026

Quality Inn Dunkirk
See all 463 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.

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 $433 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.