Old Port Holidays

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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
A tree-lined pathway leading to a brick building with a sign reading "Mercy Hospital Service Entrance".

Downtown Portland

5 out of top 10 points of interest in this area
4/5(1 area review)

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

Our pick of the best Old Port Hotel Deals

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 NZ$756 per night from 26 July to 27 July
NZ$756
26 July - 27 July
includes taxes & fees
9.4/10 Exceptional! (1,781 reviews)
"Very helpful staff and had snacks, coffee and water available 24/7"

Reviewed on 11 July 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 NZ$638 per night from 2 Aug to 3 Aug
NZ$638
2 Aug - 3 Aug
includes taxes & fees
9.4/10 Exceptional! (1,708 reviews)
"Some amenities were not available at the time of my stay."

Reviewed on 11 July 2026

Portland Regency Hotel & Spa
Hilton Garden Inn Portland Downtown Waterfront

Hilton Garden Inn Portland Downtown Waterfront

3 out of 5
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
The price is NZ$705 per night from 26 July to 27 July
NZ$705
26 July - 27 July
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Thanks"

Reviewed on 8 July 2026

Hilton Garden Inn Portland Downtown Waterfront
See all 2,435 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.

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 entertainment choices.
See properties

Activities

Portland Lighthouse Boat Cruise with Oysters & Prosecco

Portland Explorer: Boat Cruise with Oysters & Prosecco

NZ$241
per adult
Portland Explorer: Boat Cruise with Oysters & Prosecco
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

NZ$136
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Casco Bay Morning Windjammer Sail

Casco Bay Morning Windjammer Sail

NZ$107
per adult
Casco Bay Morning Windjammer Sail
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.