Old Port Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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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.
West Bayside
When in West Bayside, you can plan a visit to Merrill Auditorium and Cross Insurance Arena, some noteworthy sights in the nearby area.
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.
Top hotels in Old Port
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
S$260
16 Nov - 17 Nov
includes taxes & fees
9.2/10 Wonderful! (1,860 reviews)
"This was our favorite hotel on our trip. The property is very clean and well maintained. The restaurant food was delicious. Valet service was great. Location in town was perfect very close to shopping and activities."
Reviewed on 15 Oct, 2026
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
S$192
1 Nov - 2 Nov
includes taxes & fees
9.4/10 Exceptional! (1,778 reviews)
"Extremely well located in Portland, in the heart of the old town and central to everything. I'm glad we chose this hotel rather than others that were mostly newer. The breakfast and bar options were good."
Reviewed on 15 Oct, 2026
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
S$156
16 Nov - 17 Nov
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 great live music.
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 great live music.
Things to do
Portland: Casco Bay Morning Lighthouse Cruise
S$75
per adult
80% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
S$98
per adult
90% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
S$22
per traveller
100% of travellers recommend
* 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.