
Drakes Island Vacation Packages
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Top Drakes Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.

The Docent's Collection at 121 Middle Street
Downtown Portland
Price was CA $1,532, price is now CA $1,304 per person
CA $1,304
per person
Dec 11 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.6/10 Exceptional! (419 reviews)
The room was spacious, super clean, and well equipped. Good location in the Port. Nearby parking seems plentiful. The Docent calls itself an "aparthotel," meaning there aren't really hotel amenities. A lot of the communication with staff is done by text. Although, there was a human person at the door for most of our stay. Great choice, particularly for a long term stay given the swell kitchen, if you don't mind the concept.
Reviewed on Nov 10, 2026

The Docent's Collection at 178 Middle Street
Downtown Portland
Price was CA $1,515, price is now CA $1,360 per person
CA $1,360
per person
Dec 11 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (81 reviews)
room was very modern, however some areas did not look well cleaned (edge if the bed had some dried white liquid). the surrounding area has nice shops but is very sketchy at night. did not feel comfortable with the parking situation. also at 6am sounded like maintenance or cleaning crew was constantly in and out of the elevator making tons of noise. was good for a night but wouldnt stay again.
Reviewed on Oct 27, 2026

Portland Regency Hotel & Spa
Downtown Portland
Price was CA $1,658, price is now CA $1,506 per person
CA $1,506
per person
Dec 11 - Dec 14
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.4/10 Exceptional! (1,780 reviews)
This hotel is in a great location to all the downtown areas. We were able to walk everywhere. I didn't give it 5 stars, because I didn't know that there would be a $40 a day valet parking. It might have been somewhere in the fine print, but I missed it. The room was super quiet even with the next room being occupied. Partly I think the fan of the heating/AC unit drowned out the sounds. The fan never went off. It didn't matter the temperature. We didn't eat there either, so I'm not sure how the restaurant was.
Reviewed on Nov 10, 2026

Drakes Island Hotel Deals


Port Inn & Suites Kennebunk, an Ascend Collection Hotel
55 York St Kennebunk ME
Fully refundable
The price is CA $113 per night from Dec 1 to Dec 2
CA $113
CA $139 total
Dec 1 - Dec 2
includes taxes & fees

Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
The price is CA $154 per night from Dec 1 to Dec 2
CA $154
CA $168 total
Dec 1 - Dec 2
includes taxes & fees
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.








