Portland Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Jay

Top hotels in Portland

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 3.539.326 ₫ per night from 31 Aug to 1 Sept
3.539.326 ₫
3.999.438 ₫ total
31 Aug - 1 Sept
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 10 Aug 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 3.767.221 ₫ per night from 1 Sept to 2 Sept
3.767.221 ₫
4.257.104 ₫ total
1 Sept - 2 Sept
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
"Beautiful property right on the water. Enjoyed lunch at the hotel restaurant"

Reviewed on 5 Aug 2025

Chautauqua Harbor Hotel - Jamestown
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 2.836.033 ₫ per night from 8 Sept to 9 Sept
2.836.033 ₫
3.204.751 ₫ total
8 Sept - 9 Sept
includes taxes & fees
7/10 Good! (157 reviews)
"If you are going to an event at Chautuqua Institution this place is perfect to stsy at."

Reviewed on 9 Aug 2025

Webb's Year Round Resort
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.

Frequently asked questions

How much does a Portland holiday package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a holiday 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 holiday packages and you could score some great off-season discounts.
How many days is enough for Portland?
With a well-organised travel plan, you can easily tick off the top Portland attractions in a few days. But if you want to discover hidden gems or go on day trips, consider booking your Portland holiday for longer.
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 holiday package as early as possible.
Is it cheaper to book a Portland holiday as a package?
Expedia holiday 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 customised Portland holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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 favourite 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 personalised Portland holiday package.