Portland Holidays

Photo by Matthew Jay

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Top hotels in Portland

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 €316 per night from 2 Sept to 3 Sept
€316
2 Sept - 3 Sept
includes taxes & fees
10/10 Exceptional! (36 reviews)
"Julie was so nice when we reached out. Her place was so cute and perfect for a girls night away!!"

Reviewed on 18 Aug 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 €131 per night from 31 Aug to 1 Sept
€131
31 Aug - 1 Sept
includes taxes & fees
7.6/10 Good! (938 reviews)
"Nice place to stay nice view I will come back soon"

Reviewed on 22 Aug 2025

Clarion Hotel Conference Center on Lake Erie
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 €104 per night from 22 Sept to 23 Sept
€104
22 Sept - 23 Sept
includes taxes & fees
7/10 Good! (166 reviews)
"This resort could absolutely be described as authentically rustic. It is located right across the street from Chautauqua Lake. The rooms are dated but clean. The pool is very well maintained. But most importantly, the staff is fantastic. It is reminiscent of old New York. Lovly location and friendly ..."

Reviewed on 21 Aug 2025

Webb's Year Round Resort
See all 480 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.