Portland Holidays

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    Save up to S$134 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top hotels in Portland

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 S$181 per night from 16 Feb to 17 Feb
S$181
includes taxes & fees
16 Feb - 17 Feb
9.6/10 Exceptional! (1,000 reviews)
"I have to say this is my favorite hotel in the Chautauqua area. They have great hotel packages, swimming pool, gym and in the summer they have a pool outside and a outside bar. Inside their restaurant offers a variety of food and drinks. Great place to hang out. Their accommodations are clean, bed ..."

Reviewed on 10 Feb,2025

Chautauqua Harbor Hotel - Jamestown
Best Western Dunkirk & Fredonia Inn
Best Western Dunkirk & Fredonia Inn
2.5 out of 5
3912 Vineyard Drive, Chautauqua, Dunkirk, NY
Fully refundableReserve now, pay when you stay
The price is S$165 per night from 26 Feb to 27 Feb
S$165
includes taxes & fees
26 Feb - 27 Feb
7.8/10 Good! (883 reviews)
"."

Reviewed on 3 Feb,2025

Best Western Dunkirk & Fredonia Inn
Holiday Inn Express & Suites Jamestown, an IHG Hotel
Holiday Inn Express & Suites Jamestown, an IHG Hotel
2.5 out of 5
2811 North Main Street, Jamestown, NY
Fully refundable
The price is S$172 per night from 19 Feb to 20 Feb
S$172
includes taxes & fees
19 Feb - 20 Feb
9/10 Wonderful! (688 reviews)
"We reserved two rooms for our trip through hotels.com, but the property only had one room on our reservation. Luckily they were able to book a second room for us. Property was clean but not sparkling, another run of the vacuum would have been nice. Our 2 year old very much enjoyed the breakfast and ..."

Reviewed on 3 Feb,2025

Holiday Inn Express & Suites Jamestown, an IHG Hotel
See all 472 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.