Old Port Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

  • Rest easy

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

Top Holiday Package Deals in Old Port

Price found within the past 48 hours. Click for updated prices.
Ogunquit River Inn & Suites

Ogunquit River Inn & Suites

3 out of 5
Price was CA $1,425, price is now CA $1,144 per person
CA $1,144
per person
Jun 2 - Jun 6
found 12 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9/10 Wonderful! (1,000 reviews)
The room was very clean!

Reviewed on Oct 31, 2025

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $2,282, price is now CA $1,846 per person
CA $1,846
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (178 reviews)
The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

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 $2,473, price is now CA $2,007 per person
CA $2,007
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (291 reviews)
Beautiful space, clean room, friendly and accommodating staff, excellent location

Reviewed on Apr 5, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,030, price is now CA $1,676 per person
CA $1,676
per person
May 30 - Jun 4
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
Very well kept hotel close to everything

Reviewed on Apr 9, 2026

HomeAwhile

HomeAwhile

4 out of 5
Price was CA $1,432, price is now CA $1,212 per person
CA $1,212
per person
Jul 4 - Jul 8
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (12 reviews)
It was a perfect stay!

Reviewed on Apr 8, 2026

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

5 out of top 10 points of interest in this area
4.5/5(11 area reviews)

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
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Apr 12 to Apr 13
CA $163
CA $233 total
Apr 12 - Apr 13
includes taxes & fees
9.2/10 Wonderful! (1,765 reviews)
Very well kept hotel close to everything

Reviewed on Apr 9, 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 $175 per night from Apr 12 to Apr 13
CA $175
CA $194 total
Apr 12 - Apr 13
includes taxes & fees
9.4/10 Exceptional! (1,620 reviews)
We loved our stay here. Location is perfect! Front desk and valet are helpful and make scheduling a shuttle to the airport or train station a breeze. Zero complaints about the property and will be happy to stay here again anytime.

Reviewed on Apr 8, 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 CA $148 per night from Apr 21 to Apr 22
CA $148
CA $164 total
Apr 21 - Apr 22
includes taxes & fees
9/10 Wonderful! (1,324 reviews)
Staff very friendly and helpful. Rooms were nice and tidy but wall are thin. Close and walkable to shops and restaurants. No self parking, valet only with garage off premise with in and out available.

Reviewed on Apr 7, 2026

Hyatt Place Portland Downtown - Old Port Square
See all 2,350 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.
All Inclusive Vacations
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Frequently asked questions

How much does an Old Port vacation package cost?
From as low as CA $1,144. 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.

Things to do

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour

CA $13
per traveller
Downtown Portland: Coastal Vibe and Old Mansions with In-Add Audio Tour
Ultimate Portland Self-Guided Driving GPS Audio Tour

Ultimate Portland Self-Guided Driving GPS Audio Tour

CA $23
per traveller
100% of travellers recommend
Ultimate Portland Self-Guided Driving GPS Audio Tour
Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $21
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.