Old Port Vacation Packages

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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
Moody
Price was CA $2,048, price is now CA $1,532 per person
CA $1,532
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,005 reviews)
No curb appeal from the road at all...yet..once behind property..everything changes!.Great bed..better pillows! None of the bedside lights or plugs were functioning...and upon entering room...no air conditioning on...and the room was over 90 degrees...took over 2 hours for it to cool down.. Views are superb...pool was relaxing!

Reviewed on Jun 11, 2026

Blind Tiger Portland - Danforth Street.

Blind Tiger Portland - Danforth Street.

3.5 out of 5
West End
Price was CA $4,545, price is now CA $3,300 per person
CA $3,300
per person
Jul 19 - Jul 24
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.6/10 Exceptional! (184 reviews)
Looks better on photos than in real life. Basically a nice B&B with dated amenities and utilities. Also a bit out of the way. But its charming.

Reviewed on Jun 12, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,437, price is now CA $1,872 per person
CA $1,872
per person
Jul 19 - Jul 24
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (1,679 reviews)
We loved the hotel. The location is great and convenient to the best parts of Portland. The room was perfect with a comfortable bed a great bathroom. Staff was friendly and helpful. We would happily stay again at your hotel.

Reviewed on Jun 13, 2026

Portland Harbor Hotel

Portland Harbor Hotel

4 out of 5
Downtown Portland
Price was CA $2,254, price is now CA $1,825 per person
CA $1,825
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,781 reviews)
We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!

Reviewed on Jun 12, 2026

The Francis

The Francis

3.5 out of 5
Parkside
Price was CA $3,277, price is now CA $2,671 per person
CA $2,671
per person
Jul 19 - Jul 24
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Portland (PWM)
9.4/10 Exceptional! (391 reviews)
Great location, comfortable bed, charming property, friendly and helpful staff.

Reviewed on May 1, 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 $395 per night from Jul 5 to Jul 6
CA $395
CA $491 total
Jul 5 - Jul 6
includes taxes & fees
9.4/10 Exceptional! (1,785 reviews)
"We had a great stay! Everyone was so nice, helpful, and efficient! We loved the location. Portland is an amazing city! Wasn’t aware of the $35 a day charges but it worked out!"

Reviewed on Jun 12, 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 $356 per night from Jul 1 to Jul 2
CA $356
CA $393 total
Jul 1 - Jul 2
includes taxes & fees
9.4/10 Exceptional! (1,691 reviews)
"We loved the hotel. The location is great and convenient to the best parts of Portland. The room was perfect with a comfortable bed a great bathroom. Staff was friendly and helpful. We would happily stay again at your hotel."

Reviewed on Jun 13, 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 CA $422 per night from Jun 28 to Jun 29
CA $422
CA $466 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,013 reviews)
"Great location, really comfy bed?"

Reviewed on Jun 8, 2026

Hilton Garden Inn Portland Downtown Waterfront
See all 2,394 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 $1,532. 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

4.3/5 (275 reviews)
Catch an event at Cross Insurance Arena during your trip to Portland. Stroll along the area's waterfront or experience its acclaimed theater scene.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.