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.
USA Inn

USA Inn

2.5 out of 5
Price was CA $1,177, price is now CA $928 per person
CA $928
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
8/10 Very Good! (786 reviews)
Very low toilet, which was hard for seniors to rise from. Seal on shampoo was difficult to open. No soap dish on sink as opened soap kept sliding around. Room clean, bed n pillows comfortable. Entrance card , and internet worked fine. Location was good. A good average place to stay.

Reviewed on Jun 18, 2026

Saco Bay Hotel

Saco Bay Hotel

2.5 out of 5
Price was CA $1,656, price is now CA $1,144 per person
CA $1,144
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
7.6/10 Good! (1,068 reviews)
It is an old Ramada. A little run down but staff was very quick to act when the ac went out. They fixed it right away. The bed was very comfortable and the pool was awesome. I would recommend it.

Reviewed on Jun 19, 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 $3,493, price is now CA $2,498 per person
CA $2,498
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9.6/10 Exceptional! (328 reviews)
Such a great, different, non-hotel feeling option to stumble upon when I was in Portland, Maine. GREAT location. Feels much more boutique hotel like, quaint, way more appeal than a big "chain" hotel. I would want to book for more than a week to be able to use kitchen and flexibility of apartment-like feel.

Reviewed on Jun 12, 2026

Portland Regency Hotel & Spa

Portland Regency Hotel & Spa

3.5 out of 5
Downtown Portland
Price was CA $2,180, price is now CA $1,678 per person
CA $1,678
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (1,693 reviews)
Great location. You can walk everywhere easily. Friendly staff. The only strange thing we encountered was our room was never made up during our 3 night stay. We had the do not disturb sign out only on day 1. Not a big deal, just odd. Would stay here again.

Reviewed on Jun 19, 2026

AWOL Kennebunkport

AWOL Kennebunkport

3 out of 5
Price was CA $3,236, price is now CA $2,496 per person
CA $2,496
per person
Aug 13 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Portland (PWM)
9.4/10 Exceptional! (246 reviews)
Totally in love with overall vibes, calm and relaxation. Plus I’m DSI thankful to Staff for always welcome and helpful as I was accidentally unable to make the check-in before 7pm. I really appreciated.

Reviewed on Jun 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

4 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 $365 per night from Jun 28 to Jun 29
CA $365
CA $458 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,764 reviews)
"We didn't sleep! The AC unit banged and shuttered and roared every time it shut on throughout the night and literally made the room unsleepable. I mentioned it to the receptionist at the front desk the next morning and there was no follow up or response. It was an expensive room that we booked on ..."

Reviewed on Jun 18, 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 $331 per night from Jun 28 to Jun 29
CA $331
CA $366 total
Jun 28 - Jun 29
includes taxes & fees
9.4/10 Exceptional! (1,668 reviews)
"Great location. You can walk everywhere easily. Friendly staff. The only strange thing we encountered was our room was never made up during our 3 night stay. We had the do not disturb sign out only on day 1. Not a big deal, just odd. Would stay here again."

Reviewed on Jun 19, 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 $374 per night from Jun 21 to Jun 22
CA $374
CA $413 total
Jun 21 - Jun 22
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Love this hotel. Staff makes everything seemless. Leave your car with valet and you really don’t need it until you check out. The location, right on the waterfront, is convenient to all the shops and bars in old port. Also, The trolley and boat tours. Love the bar, and breakfast as well. No better ..."

Reviewed on Jun 17, 2026

Hilton Garden Inn Portland Downtown Waterfront
See all 2,413 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 $928. 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.

Discover the most popular places to visit in Old Port

State Theatre

State Theatre

The beautiful mix of architectural styles, from Art Deco to Moorish, makes this newly renovated performing arts venue one of New England’s best.

State Theatre
East End Beach

East End Beach

Swim in the Atlantic Ocean, stroll along the sand-and-pebble shoreline or enjoy a picnic with unbeatable views at Portland’s public beach.

East End Beach
Portland Museum of Art

Portland Museum of Art

Maine’s largest and oldest art institution showcases three centuries of American art and European masters in its architecturally impressive museum complex.

Portland Museum of Art

Things to do

Portland Self-Guided Driving Audio Tour

Portland Smartphone Audio Tour: Self-Guided Drive

CA $24
per traveller
100% of travellers recommend
Portland Smartphone Audio Tour: Self-Guided Drive
Maine Whale Watching Tour in Portland

Maine Whale Watching Tour in Portland

CA $179
per adult
Maine Whale Watching Tour in Portland
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.