Portland Vacations

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Find the Best Portland Vacation Packages

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 AED 680 per night from Apr 20 to Apr 21
AED 680
AED 1,208 total
includes taxes & fees
20 Apr - 21 Apr
10/10 Exceptional! (23 reviews)
Mommy/Daughter trip
"Perfect cottage for a relaxing weekend! We stayed to be super close to Fredonia and it was perfect! The cottage had everything we needed of our girls night!"

Reviewed on 6 April 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 AED 430 per night from May 1 to May 2
AED 430
AED 485 total
includes taxes & fees
1 May - 2 May
7.6/10 Good! (868 reviews)
"Of the options in the area this one is toward the top of the list. Great view of Lake Erie if you get a West facing room. Staff was extremely friendly. The brewery/restaurant is worth trying even if you don't stay here."

Reviewed on 4 April 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
Fully refundableReserve now, pay when you stay
The price is AED 496 per night from Apr 20 to Apr 21
AED 496
AED 561 total
includes taxes & fees
20 Apr - 21 Apr
9.6/10 Exceptional! (1,002 reviews)
"Love this hotel but the indoor pool is not maintained as well as it should be the cement around the pool needed to be power washed was a bit slimy and after using the hot tub I ended up with a severe rash all over my legs.."

Reviewed on 12 April 2025

Chautauqua Harbor Hotel - Jamestown
See all 485 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.

Frequently asked questions

How much does a Portland vacation package cost?
Offering excellent value package deals 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 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.
How to plan a trip to Portland?

  1. Choose your travel dates: The things you’d like to do in Portland and your favorite season can help you decide when to get away.
  2. Work out your budget: Make sure you have enough money to cover everything from transportation and dining out to airfares and activities. Your hotel will likely be the largest expense during your trip to Portland.
  3. Determine how many days away: Start by listing all the activities and attractions you want to experience in Portland. Then, estimate how long you’ll need for each, including any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalized Portland vacation package.