
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.

Hyatt Place Portland Downtown - Old Port Square
Downtown Portland
Price was CA $1,521, price is now CA $1,243 per person
CA $1,243
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
8.8/10 Excellent! (1,161 reviews)
The area around the property was excellent. It was safe and very walkable. There were plenty of dining options nearby. But they didn't clean the room on the second day.
Thank you,
Reviewed on Aug. 19, 2025

The Docent's Collection
Downtown Portland
Price was CA $1,965, price is now CA $1,433 per person
CA $1,433
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (219 reviews)
This property was beyond expectation. As long as you are comfortable using the app, check in was super easy and so was getting into our suite. The kitchen had everything we could have possibly needed, and having a living space was a great lift from a normal hotel room.
Reviewed on Aug. 16, 2025

Inn By The Sea
Price was CA $3,004, price is now CA $2,378 per person
CA $2,378
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (275 reviews)
We chose Inn by the Sea because it was advertised as a “pet-friendly” property with beach access for pets, which was a key factor in our decision. Unfortunately, our experience didn’t quite align with those expectations.
We arrived on a Sunday around noon and, as expected, our room wasn’t ready (check-in is at 4:00pm). However, unlike many hotels, we were not offered anything while we waited — no welcome drink, light refreshment, or even an early check-in estimate — despite having to wait the full four hours.
Once we checked in, we were told our assigned room was not pet-friendly, and we would be charged for any accidents — despite booking under the premise that this was a pet-friendly stay. Additionally, the restaurant only allows pets in the outdoor seating area, and the pool area is not pet-friendly at all. So while the hotel does accommodate pets in some areas, it’s misleading to call it fully pet-friendly when the main guest amenities are off-limits.
That said, the property is beautiful and most of the staff were friendly and professional, which we appreciated. But overall, if you’re traveling with a pet and hoping for a truly integrated experience, this may not be the best fit.
Reviewed on Aug. 18, 2025

Portland Harbor Hotel
Downtown Portland
Price was CA $1,626, price is now CA $1,303 per person
CA $1,303
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,542 reviews)
The decor and private garden were nice, as was the self-service pantry on the 2nd floor. The destination fee was a little annoying on top of the proxy room rate, as the credit for the bar was not useful for one member of our party who does not drink. Very convenient to Old Port.
Reviewed on Aug. 17, 2025

Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,584, price is now CA $1,335 per person
CA $1,335
per person
Oct 26 - Oct 31
found 8 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,368 reviews)
The Portland Regency hotel and spa was a great hotel for our family needs. We were able to stay close together and get everywhere we wanted to go on foot. The staff were amazing and even though our flight was well after check out they still stored our luggage and shuttled us to the airport. My only recommendation would be to up the bathroom cleaning a bit. Since it is a historic building and a family run business I didn't expect the facilities to be perfect but the cleaning would really up the luxury level.
Reviewed on Aug. 19, 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

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.
Old Port Hotel Deals

Portland Harbor Hotel
468 Fore Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $379 per night from Sep 1 to Sep 2
CA $379
CA $472 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (1,544 reviews)
"This place was awesome! Loved the pantry on our floor to get snacks"
Reviewed on Aug. 15, 2025

Hilton Garden Inn Portland Downtown Waterfront
65 Commercial St, Portland, ME
The price is CA $290 per night from Sep 2 to Sep 3
CA $290
CA $321 total
Sep 2 - Sep 3
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
"It was great. breakfast was great!"
Reviewed on Aug. 18, 2025

Portland Regency Hotel & Spa
20 Milk Street, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $317 per night from Aug 24 to Aug 25
CA $317
CA $350 total
Aug 24 - Aug 25
includes taxes & fees
9.4/10 Exceptional! (1,377 reviews)
"The Portland Regency hotel and spa was a great hotel for our family needs. We were able to stay close together and get everywhere we wanted to go on foot. The staff were amazing and even though our flight was well after check out they still stored our luggage and shuttled us to the airport. My only ..."
Reviewed on Aug. 19, 2025
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
Things to do

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

Portland: Sightseeing Cruise to Portland Head Light
CA $56
per adult
98% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.