Portland Vacations from $406

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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 $442, price is now $406 per person
$406
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) to Jamestown (JHW)
7.2/10 Good! (193 reviews)
Upon arrival there was no one at the desk , but the keys to our room were there with our names clearly on them. A phone next to the counter with a sign says pick up if you have any questions. So I did, person answering said we were all set. Room were clean and spacious. Breakfast in the morning was good and plentiful. Would definitely stay here again. Cheers

Reviewed on Sep 22, 2025

The Spencer Hotel & Spa

The Spencer Hotel & Spa

2.5 out of 5
Price was $563, price is now $524 per person
$524
per person
Jan 16 - Jan 18
found 1 day ago
Roundtrip flight included
Hartford (BDL) 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

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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
$317 nightly
The price is $358 total per night from Nov 12 to Nov 13
$358 total
Nov 12 - Nov 13
Total with taxes and fees
10/10 Exceptional! (45 reviews)
So cute and quaint perfect for our girls weekend !

Reviewed on Oct 8, 2025

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
$127 nightly
The price is $143 total per night from Dec 1 to Dec 2
$143 total
Dec 1 - Dec 2
Total with taxes and fees
9.6/10 Exceptional! (1,002 reviews)
Friendliness of staff.

Reviewed on Nov 8, 2025

Chautauqua Harbor Hotel - Jamestown
Quality Inn

Quality Inn

2.5 out of 5
3925 Vineyard Dr, Dunkirk, NY
$109 nightly
The price is $123 total per night from Nov 18 to Nov 19
$123 total
Nov 18 - Nov 19
Total with taxes and fees
7.6/10 Good! (504 reviews)
Staff was friendly and helpful. The ice machine was not working. Room was clean, although the carpet was stained.The toilet was unusually low, which could present a problem for some people in standing up. My room was on the first floor and looked out onto the parking lot, but the curtains were almost ...

Reviewed on Nov 5, 2025

Quality Inn
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.

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 $406 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.