Portland Vacations from $786

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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.
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
Price was $837, price is now $786 per person
$786
per person
Jul 26 - Jul 30
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Jamestown (JHW)
7.2/10 Good! (221 reviews)
They need in the room how to make coffee maker

Reviewed on Jun 7, 2026

Holiday Inn Express & Suites Jamestown by IHG

Holiday Inn Express & Suites Jamestown by IHG

2.5 out of 5
Price was $1,002, price is now $916 per person
$916
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Jamestown (JHW)
9.2/10 Wonderful! (821 reviews)
The hotel was a very nice stay. Although a few suggestions, 1) the front desk staff needs to improve there attitude/personality ( nothing major). 2) some sitting benches outside would be nice. 3) You need to step up the maintenance around the interior of the facility such as, wobbly table tops, common area bathroom doors that don't close properly, caulk and maintenance of room showers and doors. The breakfast was fantastic and the environment was peaceful. Thank you and I would stay there again! Kurt Cronin

Reviewed on Jun 7, 2026

Clarion Pointe Jamestown - Falconer

Clarion Pointe Jamestown - Falconer

2.5 out of 5
Price was $837, price is now $804 per person
$804
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Jamestown (JHW)
8/10 Very Good! (999 reviews)
Bathroom fan was very loud and couldn’t be turned off. Sheets had terrible stains.

Reviewed on Jun 3, 2026

DoubleTree by Hilton Jamestown

DoubleTree by Hilton Jamestown

4 out of 5
Price was $877, price is now $866 per person
$866
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Jamestown (JHW)
8.8/10 Excellent! (975 reviews)
Very nice and conveniently located. Staff were very friendly and helpful. Definitely recommend!

Reviewed on May 31, 2026

Sweet Mary 2 Bedroom Home by RedAwning

Sweet Mary 2 Bedroom Home by RedAwning

3.5 out of 5
Price was $1,658, price is now $1,653 per person
$1,653
per person
Jul 23 - Jul 26
found 2 hours ago
Roundtrip non-stop flight included
Melbourne (MLB) to Jamestown (JHW)
No reviews
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Portland Hotel Deals

King Lakefront Retreat on 7.5 Acres Near Wineries

King Lakefront Retreat on 7.5 Acres Near Wineries

Portland NY
10/10 Exceptional! (2 reviews)
"Absolutely beautiful stay. The property felt private, peaceful, and perfect for relaxing with family or friends. The Lake Erie views were amazing, and having so much space around the home made it feel like a true getaway.The house was clean, comfortable, and had everything we needed. The king beds ..."

Reviewed on May 4, 2026

Get rates
King Lakefront Retreat on 7.5 Acres Near Wineries
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Portland NY
$323 nightly
The price is $365 total per night from Jun 8 to Jun 9
$365 total
Jun 8 - Jun 9
Total with taxes and fees
10/10 Exceptional! (56 reviews)
"Peaceful, great location and beautiful interior/decor. Wished we could have stayed longer. Nice proximity to local vineyards and local towns. Our pups also appreciated standing on the overlook and peering out to ever changing Lake Erie."

Reviewed on May 23, 2026

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
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
$237 nightly
The price is $268 total per night from Jun 14 to Jun 15
$268 total
Jun 14 - Jun 15
Total with taxes and fees
9.6/10 Exceptional! (1,004 reviews)
"This was a beautiful place to stay. The staff was very helpful and friendly. Would hightly recommend."

Reviewed on Jun 1, 2026

Chautauqua Harbor Hotel - Jamestown
See all 470 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 $786 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.