
Bailey Island Vacation Packages
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Your Bailey Island Vacation
With one of our vacation packages to Bailey Island, you'll have endless opportunities for relaxation and adventure. There's lots to experience, including its coastal scenery and spectacular views. If sightseeing is on the cards during your trip to Bailey Island, check out popular attractions like Bailey Island Bridge, Lands End Gift Shop and Ragged Island. A few quick clicks is all it takes to build a customized Bailey Island vacation on Expedia.
Top Bailey Island Vacation Deals
Price found within the past 48 hours. Click for updated prices.


Portland Harbor Hotel
Downtown Portland
per person
Oct 10 - Oct 15
found 18 hours ago
Roundtrip non-stop flight included
St. John's (YYT) to Portland (PWM)
9.2/10 Wonderful! (1,523 reviews)
Did not like the $35 fee that charged upon check in which was for the restaurant and bar, but could not be refunded if we did not use it.
Also, the elevator situation was not ideal.
Bed was very comfortable.
Reviewed on Aug. 1, 2025


Inn at Diamond Cove
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Portland (PWM)
8.8/10 Excellent! (177 reviews)
We had an amazing stay! What a gem of an experience - all of the staff was wonderful - Antonio at the lobby cafe was so kind and friendly and Kayla at concierge always went above and beyond!!
Reviewed on Jul. 20, 2025

Blind Tiger Portland – Carleton Street
West End
per person
Oct 10 - Oct 13
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Portland (PWM)
9.8/10 Exceptional! (114 reviews)
The Blind Tiger was a gem. It was convenient and private enough to enjoy with staff available 24/7 with and questions. The room, lobby and all areas were immaculate and brilliantly arranged. I would definitely go again!
Reviewed on Jul. 23, 2025
Bailey Island Hotel Deals

Clarion Hotel Portland
1230 Congress St, Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $210 per night from Aug 11 to Aug 12
CA $210
CA $232 total
Aug 11 - Aug 12
includes taxes & fees
7.8/10 Good! (1,038 reviews)
"The lobby is welcoming. I mean spacious, clean and bright!"
Reviewed on Jul. 30, 2025

Days Inn by Wyndham Airport/Maine Mall
461 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Aug 24 to Aug 25
CA $151
CA $165 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,101 reviews)
"Outside wasn't well kept up. The room was average, clean."
Reviewed on Jul. 31, 2025

Comfort Inn Airport
90 Maine Mall Rd, South Portland, ME
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Aug 5 to Aug 6
CA $185
CA $202 total
Aug 5 - Aug 6
includes taxes & fees
8.4/10 Very Good! (1,444 reviews)
"Very friend staff"
Reviewed on Aug. 1, 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.
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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.