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Bailey Island Rentals

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Price range

Per night

$10 - $500

Bailey Island Rentals

200 Houses

Historic Captain York House: 7 Bed, 6.5 Bath

Bailey Island house

7 bedrooms / 6 bathrooms / sleeps 14

Price per night from

$493

1 / 26

Open Ocean Estate

Bailey Island house

3 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$523

1 / 28

Whitesails Cottage - Lovely deck to watch the boats, and incredible sunsets!

Bailey Island cottage

1 bedroom / 1 bathroom / sleeps 3

Price per night from

$110

1 / 15

Historic cottage with views of Mackerel Cove and right of way to Little Harbor!

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$125

1 / 13

Lovely Cape situated at the waters edge with picturesque sunset views to Mt Wash

Bailey Island house

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$450

1 / 30

Recently renovated home on a quiet road, enjoy westerly water views over Harpswe

Bailey Island house

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$150

1 / 18

Enjoy spectacular Easterly Ocean views!

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$222

1 / 22

Quaint waterfront cottage with large deck and gorgeous views!

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$110

1 / 20

Panoramic ocean views from sunrise to sunset!

Bailey Island house

2 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$200

1 / 20

Two bedroom cozy cottage with beautiful views of Mackerel Cove and the Bay!

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$125

1 / 10

McCollum Cottage -Classic Maine Cottage located on water`s edge on Bailey Island

Bailey Island cottage

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$115

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A quaint, charming and comfortable Maine cottage.

Bailey Island cottage

5 bedrooms / 1 bathroom / sleeps 6

Price per night from

$214

1 / 21

Romantic Shorefront Cottage on Harpswell Sound

Bailey Island cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$150

1 / 21

Steamboat Landing - Perched on the shore of picturesque Mackerel Cove.

Bailey Island cottage

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$200

1 / 28

Quintessential Maine Cottage Overlooking the World Famous Cribstone Bridge! Fres

Bailey Island cottage

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$135

1 / 18

Deepwater front home with beautiful sunsets

Bailey Island apartment

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$257

1 / 21

A spectacular private location with Sunrise and Sunset views.

Bailey Island cottage

4 bedrooms / 4 bathrooms / sleeps 7

Price per night from

$257

1 / 30
Viewing 38 of 200
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