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.
Microtel Inn & Suites by Wyndham York

Microtel Inn & Suites by Wyndham York

2 out of 5
Price was CA $996, price is now CA $838 per person
CA $838
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
8/10 Very Good! (1,007 reviews)
Very quite and clean rooms very nice just a little outdated but overall a pleasant stay

Reviewed on Aug. 29, 2025

Lake Wentworth Inn

Lake Wentworth Inn

2 out of 5
Price was CA $1,073, price is now CA $898 per person
CA $898
per person
Oct 12 - Oct 18
found 16 hours ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9.4/10 Exceptional! (469 reviews)
This is a lovely and well run hotel.

Reviewed on Aug. 30, 2025

2 River Road Inn & Cottages

2 River Road Inn & Cottages

3 out of 5
Price was CA $943, price is now CA $889 per person
CA $889
per person
Oct 13 - Oct 18
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Portland (PWM)
9/10 Wonderful! (225 reviews)
Very small but very clean! Definitely would recommend. Perfect location.

Reviewed on Aug. 24, 2025

Casco Bay Inn

Casco Bay Inn

2 out of 5
Price was CA $1,168, price is now CA $1,101 per person
CA $1,101
per person
Oct 4 - Oct 8
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8.2/10 Very Good! (1,012 reviews)
It was quiet and clean

Reviewed on Aug. 30, 2025

The Freeport Hotel, Ascend Hotel Collection

The Freeport Hotel, Ascend Hotel Collection

2 out of 5
Price was CA $1,216, price is now CA $1,160 per person
CA $1,160
per person
Oct 4 - Oct 8
just found
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
8/10 Very Good! (1,006 reviews)
Brd was confortable.

Reviewed on Aug. 26, 2025

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
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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

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 $315 per night from Sep 1 to Sep 2
CA $315
CA $348 total
Sep 1 - Sep 2
includes taxes & fees
Hilton Garden Inn Portland Downtown Waterfront
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 $327 per night from Sep 2 to Sep 3
CA $327
CA $414 total
Sep 2 - Sep 3
includes taxes & fees
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 $232 per night from Sep 1 to Sep 2
CA $232
CA $257 total
Sep 1 - Sep 2
includes taxes & fees
Portland Regency Hotel & Spa
See all 2,390 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Old Port vacation package cost?
From as low as CA $838. 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

Portland: Sightseeing Cruise to Portland Head Light

Portland: Sightseeing Cruise to Portland Head Light

CA $56
per adult
98% of travellers recommend
Portland: Sightseeing Cruise to Portland Head Light
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

CA $81
per adult
90% of travellers recommend
Sunset Lighthouse Cruise Tour from Casco Bay
Port City Light Cruise

Port City Lights Cruise

CA $56
per adult
100% of travellers recommend
Port City Lights Cruise
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.