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Vacation Rentals in Bailey Island, Maine

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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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Bailey Island things to do

 

Wolfe's Neck Woods State Park

This is a great place for nature buffs with cameras, families with kids, or people just wanting to enjoy the Casco Bay. The park itself is set up for...read more

 

Frontier

Great atmosphere and service. The drink menu is fine, but I prefer wine. My mother loves the tequila based Mule drink. Beef sliders are excellent, as are...read more

 

Bowdoin College Museum of Art

Bowdoin's Museum of Art gets my thumbs up for several reasons... For one, the building has a nice neat compact footprint on the college campus that affords...read more

 

Jai Yoga

I've been going to different classes at Jai Yoga for five to six years. I can't say enough about the classes, the instructors and the great flexible...read more

 

Ring's Marine Service Inc

The staffs are very helpful and provided us with free "taxi" service. They drove the kayak to the harbor, came back, and drove us to the harbor. Then pick...read more

 

Tevake Sailing Charters

My girlfriend and I took the four hour cruise out of Cooke's Landing and enjoyed it immensely. The whole region is beautiful, and you interact with it far...read more

 

Hart Yoga

This studio is clean and professional. The instructor was detailed in every move and gave quick examples for me since I was new to the studio. I gave it 4...read more

 

Giant's Stairs Trail

Beautiful! A must-see if you're around Bailey Island. If you don't want to do a ton of climbing, that's possible- there is a dirt/gravel trail that you can...read more

 

Captain Morrill's--A Community Arts Center

I am going to get this out of the way: I am biased. Steve Black, the owner/instigator of this local arts center is a friend. He's a man who grew up on the...read more

 

Maine State Music Theatre

What a great experience. Loved the theater. Seats were comfy and not too close to your neighbor. Small intimate theater. We saw 7 brides for 7 brothers. Vey...read more

 

Maine Sailing Partners

Sails, Canvas, Rigging and Service since 1983read more

 

Eveningstar Cinema

This Cinema was a lot of fun when I was in High School and when the Base was still open. Some nights the whole parking lot would be filled right up. Sadly...read more

 

Flavors of Freeport

Wasn't quite sure what to expect, but was pleasantly surprised by the event. The variety of food vendors was vast, and every single bite I had was...read more

 

Lincoln Canoes & Kayaks

Wow! I was completely shocked to read these reviews! My husband and I have been on one 5 day (Allagash) and one 4 day (Moose Bow River) canoe trip with...read more

 

Yankee Lanes of Brunswick

Great, safe and convent place to bring my family. I wish the bathrooms were more updated but overall we love it here!read more

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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 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

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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Private Oceanfront Retreat
Bailey Island Cottage Rental Picture
  • bedrooms 3
  • rental type Cottage
  • owner badgeowner badge
  • sleeps 6
  • baths 2
  • rates (USD)
 
 
 
 
 

24 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

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
    $1,500 - $2,450 /wk
 
 
 
 
 

10 reviews write a review

Ocean View Vacation Rental. Newly Renovated Top To Bottom. WiFi.
Bailey Island House Rental Picture
  • bedrooms 2
  • rental type House
  • sleeps 6
  • baths
  • rates (USD) $143 - $257 /nt
    $800 - $1,800 /wk
 
 
 
 
 

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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