Portland Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Portland Vacation Deals

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 CA $1,877, price is now CA $1,718 per person
CA $1,718
per person
Dec 12 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jamestown (JHW)
6.6/10 (343 reviews)
Room got changed due to the one I selected not being ready. Everything was comfortable and good other than there being no cups in the room. Not sure if they offer any breakfast I didn't see or smell any but my gf said she seen a Keurig and a couple snacks the night before nbd. I also think they may be under staffed.. It was definitely different than big name chain hotels and that may be partal cause for some of the mixed reviews due to people's explanations but overall it was a pleasant stay with a homey feel to it..

Reviewed on Nov 4, 2026

4358 W. Lake Road 3 Bedroom Home by RedAwning

4358 W. Lake Road 3 Bedroom Home by RedAwning

3.5 out of 5
Price was CA $3,031, price is now CA $2,754 per person
CA $2,754
per person
Dec 12 - Dec 18
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Jamestown (JHW)
No reviews

Ready to book your vacation to Portland?

 

Choose your dates

Portland Hotel Deals

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

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

Portland NY
Fully refundable
The price is CA $289 per night from Nov 16 to Nov 17
CA $289
CA $485 total
Nov 16 - Nov 17
includes taxes & fees
10/10 Exceptional! (66 reviews)
"This place is great. Perfect location and beautiful view of Lake Erie. Bed super comfy and the bathroom tub makes you feel like you’re at a spa."

Reviewed on Oct 17, 2026

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Webb's Year Round Resort

Webb's Year Round Resort

2.5 out of 5
125 W Lake Rd Mayville NY
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 6 to Nov 7
CA $150
CA $169 total
Nov 6 - Nov 7
includes taxes & fees
6.6/10 (349 reviews)
"Room got changed due to the one I selected not being ready. Everything was comfortable and good other than there being no cups in the room. Not sure if they offer any breakfast I didn't see or smell any but my gf said she seen a Keurig and a couple snacks the night before nbd. I also think they may ..."

Reviewed on Nov 4, 2026

Webb's Year Round Resort
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 CA $177 per night from Dec 1 to Dec 2
CA $177
CA $200 total
Dec 1 - Dec 2
includes taxes & fees
Chautauqua Harbor Hotel - Jamestown
See all 464 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

Stay near popular Portland attractions

21 Brix Winery

You can enjoy a tasting or tour at 21 Brix Winery during your travels to Portland.
See properties

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals from CA $1,718 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.

Explore a world of travel with Expedia

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