Drakes Island Vacation Packages
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Top Drakes Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.
84 Main
Price was CA $1,365, price is now CA $1,065 per person
CA $1,065
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
10/10 Exceptional! (52 reviews)
Very spacious and relaxing. Nice view of Kennebunk quaint ice rink and Main Street. Coffee shop at Street level was a fantastic add! Beds and bedding were comfortable. Will visit again! Nothing lacking with respect to amenities.
Reviewed on Dec 29, 2025
Cliff House Maine
Bald Head
Price was CA $2,857, price is now CA $2,139 per person
CA $2,139
per person
May 7 - May 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.4/10 Exceptional! (1,001 reviews)
Excellent stay! One of the best in New England!
Reviewed on Feb 22, 2026
Blind Tiger Portland - Danforth Street.
West End
Price was CA $1,634, price is now CA $1,332 per person
CA $1,332
per person
Apr 11 - Apr 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Portland (PWM)
9.6/10 Exceptional! (161 reviews)
The whole was cozy!
Well curated style and knowledgeable staff.
Reviewed on Jan 5, 2026
Drakes Island Hotel Deals
Drakes Island Beach Front Breathtaking Property : Oceanviews and Sandy Beach !
Wells ME
10/10 Exceptional! (53 reviews)
Host was very welcoming. Explained everything we needed to know about arrival and departure and use of amenities in the home
Reviewed on Jan 3, 2026
Anchorage Inn and Resort
265 Long Beach Avenue York Beach ME
The price is CA $136 per night from Feb 25 to Feb 26
CA $136
CA $148 total
Feb 25 - Feb 26
includes taxes & fees
8.8/10 Excellent! (1,073 reviews)
room was a little small, but perfect for 2 people. room was clean and neat and wasn’t sketchy at all. view of ocean staff was pretty. the only downside was, is the walls are a little thin where you can hear the people next to you. staff was super nice and accommodating, recommend for a stay!
Reviewed on Feb 24, 2026
Cliff House Maine
591 Shore Road Cape Neddick ME
The price is CA $602 per night from Feb 28 to Mar 1
CA $602
CA $713 total
Feb 28 - Mar 1
includes taxes & fees
9.4/10 Exceptional! (1,011 reviews)
Above and beyond!
Reviewed on Feb 23, 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.
Discover the most popular places to visit in Drakes Island
Merriland Farms Golf Course
Enjoy a round of golf in Wells at Merriland Farms Golf Course. Wander the beautiful beaches and seaside in this family-friendly area.
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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.
