Portland Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Portland Holiday
Our pick of the best Portland Hotel Deals
Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
Portland NY
NZ$590
27 Aug - 28 Aug
includes taxes & fees
10/10 Exceptional! (63 reviews)
"The interior exceeds expectations! Great for myself and a friend to cook and have some quality time catching up. The view of the lake from the seating for two is beautiful and we got to do some fun bird watching. My friend who enjoys cooking said it is extremely well equipped for cooking! Lots of ..."
Reviewed on 5 Aug 2026
Webb's Year Round Resort
125 W Lake Rd Mayville NY
Fully refundableReserve now, pay when you stay
NZ$182
8 Sept - 9 Sept
includes taxes & fees
6.6/10 (306 reviews)
"We choose this place because of the price in hopes it would be cheap and cheerful. But no. The place is run down and kinda sad. Shreading astroturf on the exterior balcony and stairs. A paint job from the 60s and basics, like blankets and cups lacking in the room."
Reviewed on 23 Aug 2026
Chautauqua Harbor Hotel - Jamestown
10 Dunham Ave Celoron NY
Fully refundableReserve now, pay when you stay
NZ$304
2 Sept - 3 Sept
includes taxes & fees
9.6/10 Exceptional! (1,011 reviews)
"Lovely stay for a 50 yr. reunion. Excellent facilities, amenities, restaurants and staf! Would stay here again! Thank you!"
Reviewed on 22 Aug 2026
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.
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?
- 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.
- 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.
- 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.
- 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.
