Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Ready to book your vacation to Portland?

 

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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
The price is CA $285 per night from Sep 4 to Sep 5
CA $285
CA $492 total
Sep 4 - Sep 5
includes taxes & fees
10/10 Exceptional! (33 reviews)
"We loved it...even got to see eagles flying around while sitting on outside deck...beautiful sunsets and chairs to watch them from. Julie was available and very nice taking care of us."

Reviewed on Jul. 31, 2025

The Fisherman's Cottage - a Lakeside Loft in the Heart of Wine Country
Clarion Hotel Conference Center on Lake Erie

Clarion Hotel Conference Center on Lake Erie

2.5 out of 5
30 Lake Shore Dr E, Dunkirk, NY
Fully refundableReserve now, pay when you stay
The price is CA $186 per night from Aug 17 to Aug 18
CA $186
CA $210 total
Aug 17 - Aug 18
includes taxes & fees
7.6/10 Good! (929 reviews)
"It was by the water and close to where we were going. Bathroom definitely needs updated or cleaned better"

Reviewed on Aug. 10, 2025

Clarion Hotel Conference Center on Lake Erie
Chautauqua Harbor Hotel - Jamestown

Chautauqua Harbor Hotel - Jamestown

3.5 out of 5
10 Dunham Ave, Celoron, NY
The price is CA $198 per night from Sep 1 to Sep 2
CA $198
CA $224 total
Sep 1 - Sep 2
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Beautiful property right on the water. Enjoyed lunch at the hotel restaurant"

Reviewed on Aug. 5, 2025

Chautauqua Harbor Hotel - Jamestown
See all 477 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation to Portland costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Portland?
Plan your trip for the low season and you're likely to get cheap Portland vacation packages. Keep in mind that school vacation periods and major festivals and events can impact prices, so do a little research before you go.
How many days is enough for Portland?
Typically, a handful of days is enough to go to the main attractions during your Portland vacation. However, if you'd like to have some time to chill out or take day tours, think about extending your trip.
How to find the best Portland package deals?
Begin your search for a Portland package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Property type," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Portland package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Portland escape off to a flying start.
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 enjoy significant savings. You'll typically snag a better deal than booking each component individually. And you'll still get the flexibility to create a customized Portland vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Portland?
If you're considering a spur-of-the-moment Portland vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Portland?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you enjoy can all influence your decision on when to visit Portland.
  2. Set your budget: Consider costs like transportation, flights and meals when working out how much to put aside for your trip to Portland. Then, choose a property that suits your budget, whether that's an economical option or a more upscale getaway.
  3. Decide how long to go for: Now that you know more about Portland, you can figure out the ideal length of your break. Create a draft itinerary and give yourself enough time for all the things you want to do.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Portland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.