Portland Holidays

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Top hotels in Portland

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly

Portland NY
The price is €323 per night from 16 Jul to 17 Jul
€323
16 Jul - 17 Jul
includes taxes & fees
10/10 Exceptional! (58 reviews)
"After a day of traveling, enjoying the local winery was a great way to relax."

Reviewed on 25 Jun 2026

Cozy Lake-View Cottage for 4 · Wine Tasting Included · Pet Friendly
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 €134 per night from 15 Jul to 16 Jul
€134
15 Jul - 16 Jul
includes taxes & fees
6.8/10 (263 reviews)
"Strange, large, octagonal opening in the wall that connects the bathroom to the bedroom, thus no bathroom privacy at all. No television. They had to bring a cable box, install it completely and then gave a remote control that was not connected to the box, and only could access 4 channels, 3 of which ..."

Reviewed on 13 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 €112 per night from 26 Jul to 27 Jul
€112
26 Jul - 27 Jul
includes taxes & fees
7.6/10 Good! (1,009 reviews)
"Shame on Clarion Hotels for neglecting this waterfront property and letting it become a sad, shabby, not inexpensive, hotel. The room phone was broken, the room safe didn’t work, room keys didn’t work, the room was poorly lit, and the bathroom was yuck. The staff was friendly, though our room across ..."

Reviewed on 11 Jul 2026

Clarion Hotel Conference Center on Lake Erie
See all 467 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.