Bailey Island Cottages

A rocky shoreline with a boat, a house, and a forest in the background.

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Our top choices for Bailey Island cottages

A small house with a wooden deck and a porch.

1. •Tranquil 2BR Summer Home•Steps to Private Beach•

Harpswell

A two-story house with a garage and a covered porch.

2. 1 Mi to Maine Street! Mcm-style Home in Brunswick

Brunswick

includes taxes & fees

20 Oct - 21 Oct

A two-story house with a porch, surrounded by trees and a grassy yard.

3. Sweet comfy cottage on Small Point Road

Small Point

Liz J.

includes taxes & fees

24 Sept - 25 Sept

A two-story house with a gabled roof and a front porch.

4. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

Munjoy Hill

Nell F.

A two-story house with a white exterior and a black base. There is a white staircase leading to the front door, surrounded by lush greenery and flowering plants.

5. 4br2ba House parking A Peaceful Oasis on Munjoy Hill

Munjoy Hill

Janet S.

includes taxes & fees

28 Sept - 29 Sept

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Top Bailey Island Hotel Reviews

Inn at St John Portland In-Town

10/10 Excellent

"We loved how old the inn was and how it was restored. Our room was so spacious and clean. We loved this place and would highly recommend!!! One thing, steep stairs but definitely worth it. Breakfast was good and staff was great. We loved it"

Cambria Hotel Portland Downtown-Old Port

10/10 Excellent

"Hotel was incredible and accommodating! Took the family and dog and we were not disappointed. We didn't take the car from the valet once over the course of a couple of days and just enjoyed walking around the old port area. The only minor gripe would be the hotel's restaurant which was underwhelming and pricey for what you get."

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