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

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Bailey Island cottages

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

1. 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 ￥47,403
￥80,260 total
includes taxes & fees
Nov 24 - Nov 25
Sweet comfy cottage on Small Point Road
A two-story house with a gabled roof and a front porch.

2. 3BR Cottage Parking A Peaceful Oasis on Munjoy Hill

3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
Munjoy Hill
10.0 out of 10, Exceptional, (2 reviews)
"Super clean and spacious in a walkable area. "
United States
Nell F.
The price is ￥29,549
￥56,047 total
includes taxes & fees
Nov 17 - Nov 18
3BR Cottage Parking A Peaceful Oasis on Munjoy Hill
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.

3. 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, (22 reviews)
"Great house! Wonderful location with so many wonderful touches to make our stay so comfortable. We would definitely stay there again."
United States
Anonymous traveler
The price is ￥47,457
￥81,785 total
includes taxes & fees
Nov 30 - Dec 1
4br2ba House parking A Peaceful Oasis on Munjoy Hill
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

Hampton Inn Portland Downtown - Waterfront

Hampton Inn Portland Downtown - Waterfront

10/10 Excellent
"Awesome location and friendly staff. Clean and well maintained. Within walking distance to everything"
Victor 1-night trip
Posted 2 hours ago
Hampton Inn Portland Downtown - Waterfront

Find out more about Bailey Island

Bailey Island Cottages information

Number of reviews
28
Accommodation
191 Cottages
Lowest Price
￥56,047
Highest Price
￥81,785

Frequently asked questions

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