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Vacation Rentals in Bailey Island, Maine

$100 $68
about Bailey Island

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Bailey Island, Maine vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Bailey Island are added and updated every week!

Compared to hotels, Bailey Island vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Bailey Island, Maine Vacation Rentals and Tourism

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Weekly rate:

Min $0, Max $4000

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$2,000
$4,000+

Bedrooms: Min 0, Max 5

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5+







Property Type:


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has swimming pool
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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

Herricks Ocean Cottages
Bailey Island Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 5
  • baths 1
  • rates (USD) $700 - $1,000 /wk
 
 
 
 
 

2 reviews write a review

Little Harbor
Bailey Island Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 4
  • baths 1
  • rates (USD) $1,300 - $1,500 /wk
 
 
 
 
 

2 reviews write a review

Herricks Ocean Cottage #3
Bailey Island Cottage Rental Picture
  • bedrooms 2
  • community
  • rental type Cottage
  • sleeps 4
  • baths 1
  • rates (USD) $700 - $900 /wk
 
 
 
 
 

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Herricks Ocean View Cottages
Bailey Island Cottage Rental Picture
  • bedrooms 3
  • community
  • rental type Cottage
  • sleeps 5
  • baths 1
  • rates (USD) $800 - $900 /wk
 
 
 
 
 

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Harpswell Vacation Oceanfront Rental Home
Bailey Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 3
  • rates (USD) $1,750 - $2,600 /wk
 
 
 
 
 

6 reviews write a review

New Cottage Perfect for a Peaceful and Quiet stay on the Ocean with Beach
Bailey Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD) $264 - $455 /nt
    $2,450 /wk
 
 
 
 
 

10 reviews write a review

Watch the Sunset from the Large Front Deck / $1140 a week
Bailey Island House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $250 /nt
    $1,140 /wk
 
 
 
 
 

3 reviews write a review

1890 Summer Cottage on an Ocean Bluff
Bailey Island Cottage Rental Picture
  • bedrooms 5
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 8
  • baths 2
  • rates (USD) $2,100 /wk
 
 
 
 
 

9 reviews write a review