Old Port Vacation Packages

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

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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 $1,135, price is now CA $816 per person
CA $816
per person
Aug 31 - Sep 3
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9/10 Wonderful! (1,008 reviews)
•There needs to be an elevator!! Outside stairs to our room was scary enough…imagine carrying a heavy suitcase! •Hot tub? •Allowed children to run around in the lobby at 9:45pm. •Noisy room (it was located below the lobby). Sounded like a renovation was underway. •Toilet moved every time someone got off of it. A few nice touches: staff were friendly and helpful. View was great! Robes were in our room. Complimentary breakfast was okay…needed gluten free bread options. Balcony was nice to just sit and have a drink.

Reviewed on Jul 10, 2026

The Meadowmere Resort

The Meadowmere Resort

2.5 out of 5
Price was CA $1,382, price is now CA $982 per person
CA $982
per person
Aug 31 - Sep 3
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
8.6/10 Excellent! (1,000 reviews)
Wonderful but be prepared to pay for breakfast. They have coffee and a sweet something but nothing healthy or hot unless you pay for it. Great location.

Reviewed on Jul 8, 2026

Evalina Hotel

Evalina Hotel

2.5 out of 5
Downtown Portland
Price was CA $3,632, price is now CA $2,660 per person
CA $2,660
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
10/10 Exceptional! (5 reviews)
It was a spacious, clean, well thought out space with all the expected amenities. The location is ideal, and the hotel is truly a treasure.

Reviewed on Jun 28, 2026

Newagen Seaside Inn

Newagen Seaside Inn

3.5 out of 5
Price was CA $1,288, price is now CA $999 per person
CA $999
per person
Aug 31 - Sep 3
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (351 reviews)
Great view, the room was clean, grounds were well maintained and the staff helpful.

Reviewed on Jul 9, 2026

Inn By The Sea

Inn By The Sea

4 out of 5
Price was CA $3,381, price is now CA $2,627 per person
CA $2,627
per person
Sep 25 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (323 reviews)
We just love it there. It is our happy place. Beautiful grounds, comfortable, friendly and downy to earth staff. Wonderful place!

Reviewed on Jun 26, 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
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
4.5/5(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 $547 per night from Jul 26 to Jul 27
CA $547
CA $659 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (1,779 reviews)
"Only 4 rooms that were having A/C problems. Of course we had one the rooms. If the A/C isn’t working, why continue to reserve the rooms and not just fix the A/C??? Front desk attendant Dennecia was wonderful and was able to get us moved for our last night in Portland. She made the experience enjoyable. ..."

Reviewed on Jul 8, 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 $480 per night from Jul 19 to Jul 20
CA $480
CA $531 total
Jul 19 - Jul 20
includes taxes & fees
9.4/10 Exceptional! (1,705 reviews)
"This is our favorite place to stay in Portland. Close to everything, great staff, historic building, comfortable bed and pillows. They could improve on the food offerings."

Reviewed on Jul 10, 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 $452 per night from Jul 12 to Jul 13
CA $452
CA $500 total
Jul 12 - Jul 13
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"Thanks"

Reviewed on Jul 8, 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.
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Frequently asked questions

How much does an Old Port vacation package cost?
From as low as CA $816. 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 entertainment choices.
See properties

Things to do

Portland Explorer: Cultural/Historical & 3 Lighthouses Tour

Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour

CA $112
per adult
100% of travellers recommend
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

CA $98
per adult
94% of travellers recommend
Afternoon Windjammer Cruise Along the Coast of Portland Maine
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

CA $109
per adult
88% of travellers recommend
Sunset Windjammer Cruise Along the Coast of Portland Maine
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.