Old Port Holidays
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Your Old Port Holiday
Planning your next adventure just got easier with a holiday package to Old Port. Take in the best this neighbourhood has to offer while creating wonderful memories that will last forever. Wondering where to go during your trip to Old Port? Nearby attractions like Portland Museum of Art, University of Southern Maine and Victoria Mansion are excellent places to start. Stop daydreaming and start doing. When it's time to book your dream holiday to Old Port, Expedia is here to help.
Our guide on where to stay in Old Port
Find the best Old Port areas and neighborhoods for the activities you enjoy most. Learn more about Old Port
Downtown Portland
5 out of top 10 points of interest in this area
A noteworthy feature of Downtown Portland is its captivating waterfront views. While you're in town, be sure to stop and check out Cross Insurance Arena and Merrill Auditorium.
West End
If you're spending some time in West End, Victoria Mansion and Portland Fire Museum are top sights worth seeing.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
Parkside
If you're spending some time in Parkside, Fitzpatrick Stadium and Neal S. Dow House are top sights worth seeing.
East Bayside
If you're spending some time in East Bayside, Maine Jewish Museum and Cathedral of the Immaculate Conception are top sights worth seeing.
Our pick of the best Old Port Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
AU$515
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (1,825 reviews)
"Nice hotel. Room was comfortable. $35 dollar a day amenity charge that was unexpected-use in restaurant. $45 dollar a day valet parking in attached garage. Elevator slow and needs cleaning. Good location to seafront restaurants."
Reviewed on 2 Sept 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
AU$401
7 Sept - 8 Sept
includes taxes & fees
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
AU$287
7 Sept - 8 Sept
includes taxes & fees
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 an Old Port holiday package cost?
From as low as . Yes, you read that right. Our Old Port holiday packages are a simple way to stretch your budget. Bundle your hotels, flights and rental car and get to know this exciting destination.
How do I get a cheap travel package to Old Port?
You'll save big if you bundle your car rentals, hotels and flights into an Old Port holiday package. Sometimes cheap means fewer choices. But not with Expedia. We offer more than 550 partner airlines and 1 000 000 hotels globally, so you'll always have plenty of variety to choose from. Eager to save even more? Add some popular activities to your package deal to unlock even bigger bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Old Port?
A trip to Old Port isn't complete until you've seen University of Southern Maine and Portland Museum of Art. Look for somewhere to stay as close as possible so you can easily access these awesome sights.
What are the top hotels in Old Port?
If this will be your first visit to Old Port, book a room at The Docents Collection or Canopy by Hilton Portland Waterfront. Both will make you feel at home and are top options with many travellers.
How far in advance should I book my Old Port holiday?
Get rewarded with the biggest variety and the cheapest prices by booking your Old Port adventure early. Airlines generally advertise flight tickets around a year before departure, so start your planning as soon as you can. Having said that, Expedia is committed to giving you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Old Port travel package include?
Much of that is up to you. You can select from a range of Old Port bundles, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car and a flight. Once you've made your booking, you can add the fun stuff like experiences and activities. Whatever your ideal Old Port trip looks like, get set to save!
What should I know before booking an Old Port travel package?
Whether it's adventure or relaxation you're craving, an Old Port holiday package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodation with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with an Old Port Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our holiday packages give you the freedom to take your pick of available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Port holiday package?
Yes you can, and we're here to help. You may be able to amend or cancel your Old Port holiday package for free within 24 hours of booking. However, you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If life throws you a curveball, visit our Customer Service Portal for more information.
Stay near popular Old Port attractions
Cross Insurance Arena
8.6/10 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its great live music.
Fore Street Gallery
You can spend an afternoon exploring the galleries in Fore Street Gallery during your travels in Portland. Experience the area's entertainment choices and great live music.
Maine Sports Hall of Fame
You can spend an afternoon exploring the galleries in Maine Sports Hall of Fame during your trip to Portland. Stroll along the area's seaside or experience its acclaimed theatre scene.
N.W. Barrett Gallery
You can spend time studying the exhibits at N.W. Barrett Gallery in Portland. Stroll along the area's waterfront or experience its entertainment choices.
Activities
Portland Smartphone Audio Tour: Self-Guided Drive
AU$24
per traveller
100% of travellers recommend
Portland, Maine: Hidden Histories Guided Walking Tour
AU$75
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.