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

Search Bailey Island Cottage Rentals from CA $377

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Check prices for these dates

In two weeks
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Bailey Island cottages

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

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

1 Mi to Maine Street! Mcm-style Home in Brunswick
3.0 star property
Brunswick
The price is CA $142
CA $377 total
includes taxes & fees
Sep 23 - Sep 24
1 Mi to Maine Street! Mcm-style Home in Brunswick
A two-story house with a porch, surrounded by trees and a grassy yard.

2. Sweet comfy cottage on Small Point Road

Sweet comfy cottage on Small Point Road
Small Point
9.6 out of 10, Exceptional, (4 reviews)
"Lovely home with plenty of space and seating. Not the most comfortable of beds but we enjoyed the space. Perfect location and would love to stay again. "
United States
Liz J.
The price is CA $417
CA $779 total
includes taxes & fees
Sep 22 - Sep 23
Sweet comfy cottage on Small Point Road
A wooden deck with wicker furniture and a view of boats on the water.

3. 'Osprey Cottage' South Freeport Home on Casco Bay!

'Osprey Cottage' South Freeport Home on Casco Bay!
Freeport
8.8 out of 10, Excellent, (23 reviews)
"This was an adorable cottage in a picturesque location. The cottage was clean and comfortable, right on the water. Additional friends stayed in the adjacent Heron cottage, and we joined them on the patio for a fire one evening as summer faded to autumn."
United States
John J.
The price is CA $457
CA $898 total
includes taxes & fees
Sep 24 - Sep 25
'Osprey Cottage' South Freeport Home on Casco Bay!
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.

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

4br2ba House parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (18 reviews)
"Great place with beautiful interiors Impeccably clean!"
United States
Janet S.
The price is CA $497
CA $854 total
includes taxes & fees
Sep 28 - Sep 29
4br2ba House parking A Peaceful Oasis on Munjoy Hill
A wooden deck with wicker furniture and a view of boats on the water.

5. 'osprey Cottage' South Freeport Home on Casco Bay!

'osprey Cottage' South Freeport Home on Casco Bay!
3.0 star property
Freeport
The price is CA $549
CA $853 total
includes taxes & fees
Sep 24 - Sep 25
'osprey Cottage' South Freeport Home on Casco Bay!
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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Top Bailey Island Hotel Reviews

The Westin Portland Harborview

The Westin Portland Harborview

10/10 Excellent
"Our family of 4 had a great experience!"
Wendy 3-night trip
Posted 1 hour ago
The Westin Portland Harborview

Find out more about Bailey Island

Bailey Island Cottages information

Number of reviews
22
Accommodation
186 Cottages
Lowest Price
CA $377
Highest Price
CA $898

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