Cumberland Foreside Vacation Packages
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Your Cumberland Foreside Vacation
Lock in a Cumberland Foreside vacation package and get set to experience all this lively city has to offer. Consider basing yourself in the neighborhood of Parkside, which is good for festivals, markets and walking. Winslow Memorial Park, Gilsland Farm Audubon Center and Little John Island Preserve are just a few of the many attractions worth exploring during your trip to Cumberland Foreside. Stop daydreaming and start adventuring. Check out the multitude of options on Expedia today and put your Cumberland Foreside vacation plans into gear!
Top Cumberland Foreside Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Portland Harbor Hotel
Downtown Portland
Price was CA $1,931, price is now CA $1,399 per person
CA $1,399
per person
May 22 - May 27
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.2/10 Wonderful! (1,766 reviews)
I would definitely recommend the Portland Harbor Hotel. The location was perfect for visiting the Old Port area; one block up from the waterfront. The hotel was quiet. The rooms were well appointed (we had a courtyard view junior suite. The staff was very friendly and a pleasure to speak with. The restaurant had a very nice breakfast menu as well as a dinner menu.
Reviewed on Apr 10, 2026
Canopy by Hilton Portland Waterfront
Downtown Portland
Price was CA $2,042, price is now CA $1,637 per person
CA $1,637
per person
May 22 - May 27
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,002 reviews)
Breakfast menu needs more fruits and yogurt-a few healthy options! Hotel was great as was the staff!
Reviewed on Apr 10, 2026
Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,805, price is now CA $1,481 per person
CA $1,481
per person
May 22 - May 27
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,619 reviews)
We loved our stay here. Location is perfect! Front desk and valet are helpful and make scheduling a shuttle to the airport or train station a breeze. Zero complaints about the property and will be happy to stay here again anytime.
Reviewed on Apr 8, 2026
Cumberland Foreside Hotel Deals
The Westin Portland Harborview
157 High St Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Apr 30 to May 1
CA $192
CA $213 total
Apr 30 - May 1
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
I chose this hotel specifically because it was advertised as pet-friendly, as I was traveling with my well-trained dog. While the location was convenient and the room itself was comfortable, the experience was soured by the lack of transparency regarding the pet policy. When I booked, the additional ...
Reviewed on Apr 6, 2026
Cambria Hotel Portland Downtown-Old Port
25 HANCOCK STREET Portland ME
Fully refundable
The price is CA $156 per night from Apr 15 to Apr 16
CA $156
CA $210 total
Apr 15 - Apr 16
includes taxes & fees
9.4/10 Exceptional! (1,188 reviews)
Clean, quiet, good stay.
Reviewed on Apr 6, 2026
Portland Harbor Hotel
468 Fore Street Portland ME
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from Apr 26 to Apr 27
CA $168
CA $239 total
Apr 26 - Apr 27
includes taxes & fees
9.2/10 Wonderful! (1,767 reviews)
Wonderful staff!
Reviewed on Apr 10, 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.
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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.
