Old Port Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Downtown Portland

4 out of top 10 points of interest in this area
3.5/5(2 area reviews)

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.

Find hotels in Downtown Portland

Top hotels in Old Port

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is S$403 per night from 7 Jun to 8 Jun
S$403
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,762 reviews)
"The staff was very helpful, especially Adam, helping us negotiate places to go in Portland and answering our questions"

Reviewed on 2 Jun, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
The price is S$348 per night from 7 Jun to 8 Jun
S$348
7 Jun - 8 Jun
includes taxes & fees
9.4/10 Exceptional! (1,671 reviews)
"The Regency is a Portland institution that's located in a fantastic location. Too bad it's starting to look and sound and smell weathered. We were in room 215 and it smelled of smelly socks when we entered. The ancient air and heating system was on, but it was so loud it was hard to nap, much less ..."

Reviewed on 2 Jun, 2026

Portland Regency Hotel & Spa
Hyatt Place Portland Downtown - Old Port Square

Hyatt Place Portland Downtown - Old Port Square

3 out of 5
433 Fore St Portland ME
Fully refundableReserve now, pay when you stay
The price is S$296 per night from 7 Jun to 8 Jun
S$296
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (1,357 reviews)
"Missed the ubiquitous body cream."

Reviewed on 2 Jun, 2026

Hyatt Place Portland Downtown - Old Port Square
See all 2,368 properties in Old Port
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.

Popular places to visit

Thompson's Point

Commune with nature and explore the great outdoors at Thompson's Point during your travels in Portland. Stroll along the seaside or attend a sporting event in the area.

Thompson's Point

Fitzpatrick Stadium

Catch an event at Fitzpatrick Stadium during your trip to Portland. Amble around the area's waterfront or attend a sporting event.

Fitzpatrick Stadium

Things to do

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

S$68
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

S$19
per traveller
Portland Smartphone Audio Tour: Self-Guided Drive
See all activities in Portland

* 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.