Old Port Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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

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Top Holiday Package Deals in Old Port

Price found within the past 48 hours. Click for updated prices.
The Docent's Collection at 121 Middle Street

The Docent's Collection at 121 Middle Street

3.5 out of 5
Downtown Portland
Price was CA $1,512, price is now CA $1,293 per person
CA $1,293
per person
Dec 10 - Dec 13
found 4 hours ago
Roundtrip flight included
Toronto (YTZ) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
We loved everything. The only thing is the mattress is a little soft and you easily roll to the middle!

Reviewed on Oct 27, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $2,227, price is now CA $1,884 per person
CA $1,884
per person
Dec 28 - Jan 2
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (342 reviews)

Sauna Hot Tub Game Room Theater Firepit

Sauna Hot Tub Game Room Theater Firepit

2 out of 5
Price was CA $7,517, price is now CA $6,569 per person
CA $6,569
per person
Dec 20 - Dec 26
found 10 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

River View Resort

River View Resort

2.5 out of 5
Price was CA $3,172, price is now CA $2,780 per person
CA $2,780
per person
Dec 20 - Dec 26
found 10 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (337 reviews)

Close to Sunday River Hot Tub Sauna Cold Plunge

Close to Sunday River Hot Tub Sauna Cold Plunge

2 out of 5
Price was CA $7,306, price is now CA $6,403 per person
CA $6,403
per person
Dec 20 - Dec 26
found 10 hours ago
Roundtrip flight included
Montreal (YUL) to Portland (PWM)
No reviews

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

Downtown Portland is known for its captivating waterfront views, and with sights like Cross Insurance Arena and Merrill Auditorium, you won't get bored spending a day wandering around this part of Portland.

Find hotels in Downtown Portland

Old Port Hotel Deals

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
468 Fore Street Portland ME
The price is CA $186 per night from Nov 22 to Nov 23
CA $186
CA $259 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (1,861 reviews)
"each floor had a pantry where you can make coffee. Although the downstairs coffee in the lobby emptied really fast and they didn’t really refill it very often. There’s only one elevator going up to the fourth floor, at least by the lobby. So sometimes it would get crowded. The hotel is centrally ..."

Reviewed on Oct 27, 2026

Portland Harbor Hotel
Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $177 per night from Nov 3 to Nov 4
CA $177
CA $196 total
Nov 3 - Nov 4
includes taxes & fees
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
The price is CA $148 per night from Nov 22 to Nov 23
CA $148
CA $164 total
Nov 22 - Nov 23
includes taxes & fees
9.4/10 Exceptional! (1,019 reviews)
"."

Reviewed on Oct 27, 2026

Hilton Garden Inn Portland Downtown Waterfront
See all 2,385 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.
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Frequently asked questions

How much does an Old Port vacation package cost?
From as low as CA $1,293. Yes, you read that right. Our Old Port vacation 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 vacation 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 travelers.
How far in advance should I book my Old Port vacation?
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 vacation!
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 vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your accommodations with your flights and rental car. The more you bundle, the bigger the savings!
Can I choose my airline with an Old Port Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our vacation 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 vacation package?
Yes you can, and we're here to help. You may be able to amend or cancel your Old Port vacation 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.
See properties

Things to do

Harbor Lights and Sights Cruise

Harbor Lights and Sights Cruise

CA $86
per adult
90% of travellers recommend
Harbor Lights and Sights Cruise
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
92% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
Portland: Casco Bay Morning Lighthouse Cruise

Portland: Casco Bay Morning Lighthouse Cruise

CA $83
per adult
80% of travellers recommend
Portland: Casco Bay Morning Lighthouse Cruise
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.