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Bailey Island Rentals

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Price range

Per night

$10 - $500

Bailey Island Rentals

227 apartments

$493

Historic Captain York House: 7 Bed, 6.5 Bath

Bailey Island house

7 bedrooms / 6 bathrooms / Sleeps 14

$493

1 / 26

$525

Open Ocean Estate

Bailey Island house

3 bedrooms / 4 bathrooms / Sleeps 10

$525

1 / 28

$200

Enjoy spectacular Easterly Ocean views!

Bailey Island cottage

3 bedrooms / 2 bathrooms / Sleeps 6

$200

1 / 22

$1,500

A quaint, charming and comfortable Maine cottage.

Bailey Island cottage

5 bedrooms / 1 bathroom / Sleeps 6

$1,500

1 / 21

$2,500

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

Bailey Island house

4 bedrooms / 4 bathrooms / Sleeps 7

$2,500

1 / 30

$100

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

Bailey Island cottage

1 bedroom / 1 bathroom / Sleeps 3

$100

1 / 15

$200

Panoramic ocean views from sunrise to sunset!

Bailey Island house

2 bedrooms / 2 bathrooms / Sleeps 8

$200

1 / 20

$110

Quaint waterfront cottage with large deck and gorgeous views!

Bailey Island cottage

2 bedrooms / 1 bathroom / Sleeps 5

$110

1 / 20

$225

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

Bailey Island cottage

3 bedrooms / 2 bathrooms / Sleeps 6

$225

1 / 28

$129

Quintessential Maine Cottage Overlooking the World Famous Cribstone Bridge! Fres

Bailey Island cottage

2 bedrooms / 1 bathroom / Sleeps 6

$129

1 / 18

$150

Spectacular sunset views from the wrap-around deck of this comfortable ranch.

Bailey Island cottage

2 bedrooms / 2 bathrooms / Sleeps 6

$150

1 / 18

$1,800

A spectacular private location with Sunrise and Sunset views.

Bailey Island cottage

4 bedrooms / 4 bathrooms / Sleeps 7

$1,800

1 / 25

$115

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

Bailey Island cottage

3 bedrooms / 2 bathrooms / Sleeps 6

$115

1 / 13

$175

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

Bailey Island house

2 bedrooms / 3 bathrooms / Sleeps 6

$175

1 / 18

$125

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

Bailey Island cottage

2 bedrooms / 2 bathrooms / Sleeps 5

$125

1 / 19

$125

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

Bailey Island cottage

2 bedrooms / 1 bathroom / Sleeps 5

$125

1 / 10

$120

Romantic Shorefront Cottage on Harpswell Sound

Bailey Island cottage

1 bedroom / 1 bathroom / Sleeps 2

$120

1 / 21

$257

Deepwater front home with beautiful sunsets

Bailey Island apartment

3 bedrooms / 2 bathrooms / Sleeps 6

$257

1 / 21
Viewing 38 of 227
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