Name: Portland Regency Hotel & Spa
Price range: CA $185
Rating: 9.4

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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.

Ogunquit River Inn & Suites

CA $698

per person

May 22 - May 24

found 12 hours ago

Roundtrip flight included

Toronto (YTO) to Portland (PWM)

9/10 Wonderful! (1,000 reviews)

The room was very clean!

Reviewed on Oct 31, 2025

Portland Harbor Hotel

Downtown Portland

CA $1,769

per person

May 26 - Jun 2

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9.2/10 Wonderful! (1,776 reviews)

Our stay here was awesome! Very clean and gorgeous room.

Reviewed on Mar 16, 2026

The Weldon Hotel

Downtown Portland

CA $2,050

per person

May 26 - Jun 2

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9.8/10 Exceptional! (94 reviews)

Clean and comfortable. The gym was great.

Reviewed on Mar 6, 2026

Blind Tiger Portland - Danforth Street.

West End

CA $2,481

per person

May 26 - Jun 2

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9.6/10 Exceptional! (175 reviews)

The Blind Tiger was one of the best accommodations I've ever stayed in! The location was perfect – far enough away from the "bustle" of downtown but close enough to walk to many spots (Smalls was a favorite!). The daily breakfast was so great and the room, my goodness! Adorable, perfect, comfortable... best sleep of my life! Maggie was so helpful and accommodating and made our stay really special. All in all, highly recommend!

Reviewed on Mar 10, 2026

The Docent's Collection at 121 Middle Street

Downtown Portland

CA $2,221

per person

May 26 - Jun 2

found 3 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to Portland (PWM)

9.6/10 Exceptional! (273 reviews)

Loved this hotel! Our room was spacious, clean, and the staff was very responsive and accommodating. We had a plane cancellation so we had to book an additional 1 night stay last minute and that was not an issue. 100% would recommend!

Reviewed on Mar 16, 2026

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Bailey Island Hotel Deals

The Westin Portland Harborview

157 High St Portland ME

Fully refundableReserve now, pay when you stay

CA $134

CA $149 total

Apr 5 - Apr 6

includes taxes & fees

8.8/10 Excellent! (1,003 reviews)

Just a great place to stay

Reviewed on Mar 10, 2026

Clarion Hotel Portland Airport ME

1230 Congress St Portland ME

Fully refundable

CA $106

CA $117 total

Mar 24 - Mar 25

includes taxes & fees

8/10 Very Good! (1,403 reviews)

Nice room with shuttle. Hot tub was not working.

Reviewed on Mar 16, 2026

Portland Regency Hotel & Spa

20 Milk Street Portland ME

Fully refundableReserve now, pay when you stay

CA $185

CA $205 total

Mar 17 - Mar 18

includes taxes & fees

9.4/10 Exceptional! (1,602 reviews)

The shuttle to the downtown area is a perk not advertised which is a great option

Reviewed on Mar 16, 2026

See all 1,765 properties in Bailey Island

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.