Portland Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 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

Top hotels in Portland

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 S$197 per night from 9 Jul to 10 Jul
S$197
9 Jul - 10 Jul
includes taxes & fees
7/10 Good! (254 reviews)
"Staff was very friendly and helpful and the rooms were clean and updated however, the bathrooms could use a makeover!"

Reviewed on 6 Jul, 2026

Webb's Year Round Resort
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 refundable
The price is S$163 per night from 20 Jul to 21 Jul
S$163
20 Jul - 21 Jul
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Espectacular!!!"

Reviewed on 6 Jul, 2026

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 S$346 per night from 21 Jul to 22 Jul
S$346
21 Jul - 22 Jul
includes taxes & fees
9.6/10 Exceptional! (1,011 reviews)
"Room was spotless and very comfortable. Front desk staff is great, and Brian is always so helpful and accommodating! Has always gone above and beyond to make our stays memorable!"

Reviewed on 7 Jul, 2026

Chautauqua Harbor Hotel - Jamestown
See all 466 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.

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 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.

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. 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.