Portland Vacations from $687

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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.
Quality Inn Falconer - Jamestown

Quality Inn Falconer - Jamestown

2.5 out of 5
Price was $701, price is now $687 per person
$687
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Jamestown (JHW)
7.6/10 Good! (1,002 reviews)
No WiFi, breakfast needs attention

Reviewed on Nov 17, 2025

Clarion Pointe Jamestown - Falconer

Clarion Pointe Jamestown - Falconer

2.5 out of 5
Price was $706, price is now $688 per person
$688
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) 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 $720, price is now $704 per person
$704
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Jamestown (JHW)
8.4/10 Very Good! (1,000 reviews)
Clean room, good breakfast. Staff was nice.

Reviewed on Jan 5, 2026

Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
Price was $721, price is now $709 per person
$709
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Jamestown (JHW)
9.2/10 Wonderful! (787 reviews)
They had bacon for breakfast.

Reviewed on Jan 1, 2026

Hampton Inn & Suites Jamestown

Hampton Inn & Suites Jamestown

2.5 out of 5
Price was $730, price is now $724 per person
$724
per person
Mar 27 - Mar 29
found 1 day ago
Roundtrip non-stop flight included
Las Vegas (LAS) to Jamestown (JHW)
9.2/10 Wonderful! (889 reviews)
Staff was excellent, rooms nice and breakfast was good

Reviewed on Dec 29, 2025

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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
The price is $336 total per night from Jan 25 to Jan 26
$336 total
per night
Jan 25 - Jan 26
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
The price is $124 total per night from Jan 26 to Jan 27
$124 total
per night
Jan 26 - Jan 27
9.6/10 Exceptional! (1,001 reviews)
The restaurant was great and the bar had great choices.

Reviewed on Jan 8, 2026

Chautauqua Harbor Hotel - Jamestown
The White Inn

The White Inn

2 out of 5
52 E Main Rd Fredonia NY
Fully refundableReserve now, pay when you stay
The price is $128 total per night from Feb 7 to Feb 8
$128 total
per night
Feb 7 - Feb 8
9.4/10 Exceptional! (64 reviews)
Clean room, updated bath with heated floor, elegantly decorated

Reviewed on Jan 17, 2026

The White Inn
See all 462 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 $687 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.