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.
The Meadowmere Resort
CA $1,575
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Portland (PWM)
8.6/10 Excellent! (1,010 reviews)
Clean room, paid breakfast, front office staff very efficient, very limited items even in paid breakfast section.check in time 4 pm and check out 11 am.
Reviewed on Sep 2, 2026
White Barn Inn & Spa, Auberge Collection
CA $4,869
per person
Oct 2 - Oct 4
found 4 hours ago
Roundtrip flight included
Kitchener (YKF) to Portland (PWM)
9.4/10 Exceptional! (123 reviews)
An amazing experience.
Wonderful place, wonderful accommodation (we had the loft suite). Staff was great and smiling.
Reviewed on Aug 10, 2026
Ogunquit River Inn & Suites
Moody
CA $1,356
per person
Oct 7 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9/10 Wonderful! (1,022 reviews)
Nice clean rooms, perfect outdoor space for kids, felt safe. Rooms were quiet, breakfast was great, nice friendly stuff
Reviewed on Sep 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
4 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.
West End
Distinguished by its well-preserved Victorian architecture, this downtown Portland neighborhood boasts the scenic Western Promenade park, offering views of the White Mountains, and several historic structures, such as the Gothic House and Morrill Mansion.
Portland Arts District
The ample dining options and captivating waterfront views are top of the list for many visitors to Portland Arts District. A stop by Cross Insurance Arena or Portland Museum of Art might round out your trip.
East Bayside
Bordered by Franklin Street and Washington Avenue, East Bayside offers a community arts venue, Mayo Street Arts, and the relaxing green space of Kennedy Park. Explore nearby Old Port and Munjoy Hill.
West Bayside
If you're looking for some top things to see and do in West Bayside and surrounding area, you can visit Merrill Auditorium and Cross Insurance Arena.
Old Port Hotel Deals
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
CA $438
CA $537 total
Sep 7 - Sep 8
includes taxes & fees
Portland Regency Hotel & Spa
20 Milk Street Portland ME
Fully refundableReserve now, pay when you stay
CA $378
CA $418 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,731 reviews)
"Room was spacious and fairly quiet. Location was great for exploring Portland."
Reviewed on Sep 2, 2026
Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St Portland ME
Fully refundableReserve now, pay when you stay
CA $260
CA $288 total
Sep 7 - Sep 8
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
"The hotel very nice the room was ok"
Reviewed on Sep 1, 2026
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 vacation package cost?
From as low as CA $1,219. 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.
Fore Street Gallery
You can spend an afternoon studying the exhibits at Fore Street Gallery during your trip to Portland. Experience the area's entertainment choices and acclaimed theater scene.
Maine Sports Hall of Fame
You can spend an afternoon studying the exhibits at Maine Sports Hall of Fame during your travels in Portland. Stroll along the area's seaside or experience its acclaimed theater scene.
N.W. Barrett Gallery
You can spend time browsing the exhibits at N.W. Barrett Gallery during your trip to Portland. Stroll along the area's waterfront or experience its entertainment choices.
Things to do
Sunset Windjammer Cruise Along the Coast of Portland Maine
CA $107
per adult
90% of travellers recommend
Morning Lighthouse Cruise Along the Coast of Portland Maine
CA $82
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.