Bailey Island, Maine

Vacation Rentals in Bailey Island, Maine

Discover 34 vacation rental properties in Bailey Island. From 1 to 5 bedrooms. Average $292/night. 100% have pools.

34 verified listings Book securely on VRBO Prices updated March 2026

34 properties available

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$474/night
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The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

The perfect seaside retreat overlooking scenic Mackerel Cove on Bailey Island

1 bed 1 bath
PoolA/CWiFiBalcony
$188/night
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Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

Sea Ledge S - Enjoy beautiful sunsets from this charming Bailey Isl cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$215/night
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Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home

Sea Ledge North - Capture Breathtaking Sunsets from this Beautiful Home

2 beds 1 bath
PoolA/CWiFiBalcony
$226/night
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Sea Spray - Beautiful 2BR, 1BA cottage with expansive views of Casco Bay

Sea Spray - Beautiful 2BR, 1BA cottage with expansive views of Casco Bay

2 beds 1 bath
PoolA/CWiFiBalcony
$277/night
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Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay

Pet-friendly Quintessential Maine Cottage with Easterly Views of Casco Bay

2 beds 1 bath
PoolA/CWiFiBalcony
$160/night
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Cozy 2 bedroom cottage with beautiful views of Mackerel Cove!

Cozy 2 bedroom cottage with beautiful views of Mackerel Cove!

2 beds 1 bath
PoolA/CWiFiBalcony
$152/night
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Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island

Enjoy breathtaking sunsets from this newly renovated studio on Bailey Island

1 bath
PoolA/CWiFiBalcony
$160/night
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Ocean Breeze Cottage with Open Water Views of Casco Bay

Ocean Breeze Cottage with Open Water Views of Casco Bay

2 beds 1 bath
PoolA/CWiFiBalcony
$343/night
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Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

Sunrise Cottage. Relaxing waterfront deck on the rocky shore of Bailey Island.

2 beds 1 bath
PoolA/CWiFiBalcony
$386/night
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The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

3 beds 2 baths
PoolA/CWiFiBalcony
$602/night
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Historic cottage with right of way to Little Harbor!

Historic cottage with right of way to Little Harbor!

3 beds 1 bath
PoolA/CWiFiBalcony
$165/night
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Enjoy beautiful easterly views of Casco Bay from this charming 1BR cottage

Enjoy beautiful easterly views of Casco Bay from this charming 1BR cottage

1 bed 1 bath
PoolA/CWiFiBalcony
$170/night
View Details → Book on VRBO
Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

Ole Greeley Cottage - Classic oceanfront, pet-friendly Bailey Island cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$215/night
View Details → Book on VRBO
The Anchorage - Charming Bailey Isl cottage with beautiful views of Casco Bay

The Anchorage - Charming Bailey Isl cottage with beautiful views of Casco Bay

3 beds 1 bath
PoolA/CWiFiBalcony
$196/night
View Details → Book on VRBO
Couples Cottage at Mackerel Cove - Enjoy your views of Mt. Washington on the Rooftop Deck!

Couples Cottage at Mackerel Cove - Enjoy your views of Mt. Washington on the Rooftop Deck!

1 bed 1 bath
PoolA/CWiFiBalcony
$174/night
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Enjoy picturesque inlet views of a working harbor and sunny days at your oceanfront cottage

Enjoy picturesque inlet views of a working harbor and sunny days at your oceanfront cottage

2 beds 2 baths
PoolA/CWiFiBalcony
$255/night
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Lovely deck to watch the boats come and go, and incredible sunsets!

Lovely deck to watch the boats come and go, and incredible sunsets!

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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A perfectly placed cottage overlooking Mackerel Cove!

A perfectly placed cottage overlooking Mackerel Cove!

2 beds 3 baths
PoolA/CWiFiBalcony
$323/night
View Details → Book on VRBO
3 bedroom, 2 bathroom classic Maine cottage with ocean views into Mackerel Cove

3 bedroom, 2 bathroom classic Maine cottage with ocean views into Mackerel Cove

3 beds 2 baths
PoolA/CWiFiBalcony
$226/night
View Details → Book on VRBO
Charming 4 bedroom Classic Maine Cottage located near the giant stairs.

Charming 4 bedroom Classic Maine Cottage located near the giant stairs.

4 beds 1 bath
PoolA/CWiFiBalcony
$164/night
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Panoramic ocean views from sunrise to sunset!

Panoramic ocean views from sunrise to sunset!

2 beds 2 baths
PoolA/CWiFiBalcony
$301/night
View Details → Book on VRBO
Johnson Homestead. One level living, ocean view with semi-private beach access.

Johnson Homestead. One level living, ocean view with semi-private beach access.

4 beds 2 baths
PoolA/CWiFiBalcony
$331/night
View Details → Book on VRBO
Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

Enjoy Amazing Views, and Comfortable Spaces in this Well Appointed Sanctuary

4 beds 1 bath
PoolA/CWiFiBalcony
$803/night
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Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views

Turn-of-the-Century Classic Maine Cottage with Sweeping Southeasterly Ocean Views

4 beds 2 baths
PoolA/CWiFiBalcony
$340/night
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Homeport - Modern oceanfront cottage overlooking quintessential Mackerel Cove

Homeport - Modern oceanfront cottage overlooking quintessential Mackerel Cove

3 beds 2 baths
PoolA/CWiFiBalcony
$310/night
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PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

PRIVATE OCEANFRONT COMPOUND with spectacular ocean views from nearly every room

5 beds 4 baths
PoolA/CWiFiBalcony
$978/night
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Sweet 1 bedroom cottage tucked along Harpswell Sound' shore, quiet location and wonderful views

Sweet 1 bedroom cottage tucked along Harpswell Sound' shore, quiet location and wonderful views

1 bed 1 bath
PoolA/CWiFiBalcony
$191/night
View Details → Book on VRBO
Enjoy spectacular sunset and water views from the deck and balconies with water access.

Enjoy spectacular sunset and water views from the deck and balconies with water access.

2 beds 2 baths
PoolA/CWiFiBalcony
$222/night
View Details → Book on VRBO
This sweet cottage offers a shared pebbly beachfront and gorgeous sunset views

This sweet cottage offers a shared pebbly beachfront and gorgeous sunset views

1 bed 1 bath
PoolA/CWiFiBalcony
$174/night
View Details → Book on VRBO
Perfect spot for a couples get-away, ocean views from the balcony and sitting area

Perfect spot for a couples get-away, ocean views from the balcony and sitting area

1 bed 1 bath
PoolA/CWiFiBalcony
$226/night
View Details → Book on VRBO
Beautifully landscaped, Spacious home, conveniently located in Harpswell

Beautifully landscaped, Spacious home, conveniently located in Harpswell

3 beds 2 baths
PoolA/CWiFiBalcony
$385/night
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Quintessential Maine cottage overlooking the Cribstone Bridge with nearby beach access!

Quintessential Maine cottage overlooking the Cribstone Bridge with nearby beach access!

2 beds 1 bath
PoolA/CWiFiBalcony
$199/night
View Details → Book on VRBO
This spacious 2nd floor garage apartment offers phenomenal open ocean views!

This spacious 2nd floor garage apartment offers phenomenal open ocean views!

1 bed 1 bath
PoolA/CWiFiBalcony
$250/night
View Details → Book on VRBO

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