Experience Small-town Maine Living in Bailey Island Rentals

Bailey Island, Maine is a wonderful summer getaway destination for families and couples alike. Here, you’ll find the comfort of home in Bailey Island rentals and plenty of fun in the sun with access to neighboring Orr Island, too.

Stay in Bailey Island Rentals for a Cozy Getaway


Several Bailey Island vacation rentals have been touted for their attention to detail and rustic décor made to make visitors feel welcome. Schedule a short weekend away with your sweetie, and take advantage of the nearly world-famous seafood at one of the local restaurants, too. Choose Bailey Island, ME rentals on the beach for a romantic evening walk, or relax while watching the sunset together.

Day Trips from Bailey Island Vacation Rentals


Since the construction of the Cobwork Bridge, which connects Bailey Island to Orr Island, the choices in things to do here have literally become endless. Since you most likely will drive to stay in Bailey Island rentals, simply hop in the car and explore an additional island that offers Maine’s best food and attractions.

Bailey Island vacation rentals are also located near The Giant Steps, an interesting rock formation that looks much like a flight of stairs on the edge of the island. Bailey Island, ME rentals demand a visit to Mackerel Cove, as this is known as one of the top-photographed locations in Maine.

Access Local Beaches near Bailey Island ME Rentals


Your entire group will love a day at Land’s End, a famous beach located near Bailey Island rentals. This is an ideal location, as Bailey Island vacation rentals are located in an area famous for rocky beaches. Birds and other wildlife reside here, and you’ll find plenty of photo opportunities during mating and migrating seasons. Your choice in Bailey Island, ME rentals offers access to a multitude of activities and natural attractions the entire family can enjoy during your stay.

Still searching for the perfect vacation rental in the Portland and Casco Bay area? Consider staying in rentals in Brunswick, Cape Elizabeth rentals, Freeport vacation rentals, Harpswell lodging, Orr's Island rentals, rental lodging in Phippsburg, Popham Beach rentals, or rentals in Portland.

Bailey Island, Maine Rentals

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Quintessential Maine Home on Bailey Island with inground pool

— Property 181262
Bailey Island house rental - Winter wonderland waiting for summer fun!
3 Bedrooms, Sleeps 7,
House, 2 Bathrooms, near the ocean, village, garden
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Historic Cottage Overlooking One of Maine's most picturesque coves

— Property 134922
Bailey Island cottage rental - 2 Coves Cottage
3 Bedrooms, Sleeps 8,
Cottage, 3 Bathrooms, near the ocean, waterfront, garden
Calendar Updated Nov 3 2009

Property Review

All we expected was a charming cottage for a quick get-a-way. We went for just a night and ended up staying for over a week! You will not believe the views! This must be the most beloved...
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Waterfront vintage Maine island cottage: Special Aug/Sept discount

— Property 164879
Bailey Island cottage rental - Washburn Cottage
3 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, waterfront, TV
Calendar Updated Oct 26 2009

Property Review

A wonderful getaway on the coast of Maine. Nice cottage feel, refreshing sea-air, and sunsets that beat the band. Cooks Lobster House is a stone's throw away--yes that's walking distance--to...
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Waterfront House with Spectacular Views

— Property 242673
Bailey Island house rental - Approaching the House
4 Bedrooms, Sleeps 7,
House, 2 Bathrooms, beach, waterfront, garden
Rates - per property (USD)
$1,500 - $1,900/week
Calendar Updated Oct 21 2009

Property Review

When we arrived, we were so thrilled to see that it was better than we could have even hoped for. As we knew, we were immediately drawn to the ocean with its' ledges and pounding waves. The view...
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Killer Sunsets on Merriconeag Sound

— Property 110724
Bailey Island house rental - Watch lobster boats work their traps each day!
7 Bedrooms, Sleeps 17,
House, 6 Bathrooms, 1 Half Bath, near the ocean, village, garden
Rates - per property (USD)
$1,850 - $2,650/week
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Waterfront Home with Fantastic Bay and Sunset Views

— Property 104516
Bailey Island house rental - south side of the house
4 Bedrooms, Sleeps 9,
House, 2 Bathrooms, waterfront, garden
Rates - per property (USD)
$250 - $375/night
$1,600 - $2,600/week
$10,000/month
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Charming rustic cottage on the ocean, with semi-private beach

— Property 184120
Bailey Island cottage rental - Nezinscott front yard
5 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, beach, near the ocean, internet access
Rates - per property (USD)
$110 - $140/night
$700 - $1,100/week
Calendar Updated Oct 13 2009

Property Review

We've been guests at Bailey Island for nearly 40 summers, and each year it only gets better. The five generations of our family appreciate the warm welcome and continued friendship with the clan...
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New cottage, owner-designed, island waterfront

— Property 229351
Bailey Island cottage rental
2 Bedrooms, Sleeps 6,
Cottage, 1 Bathroom, near the ocean, waterfront, internet access
Rates - per property (USD)
$1,000/week
Calendar Updated Oct 6 2009

Property Review

I recently returned from a week at the Seabreeze cottage with my 8mo daughter, 75 yr old mother and brother. We all had a great time. The weather was perfect allowing us to only use the propane...
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Charming Cottage with Breathtaking Ocean Views, Great for the Whole Family!

— Property 252488
Bailey Island cottage rental - View of the Cottage from the front yard
3 Bedrooms, Sleeps 8,
Cottage, 2 Bathrooms, waterfront, garden
Rates - per property (USD)
$175 - $275/night
$800 - $1,600/week
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1890 Summer Cottage on an Ocean Bluff

— Property 232029
Bailey Island cottage rental - Looking up from ocean at front of the house
5 Bedrooms, Sleeps 7,
Cottage, 2 Bathrooms, rural, waterfront, internet access
Rates - per property (USD)
$1,900/week
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Our South Cabin offers Bold oceanfront with fantastic views!

— Property 175535
Bailey Island cottage rental - Mid Day from the deck!
Studio, Sleeps 3,
Cottage, 1 Bathroom, rural, waterfront, internet access
Rates - per property (USD)
$700 - $850/week
Calendar Updated Sep 28 2009

Property Review

We spent a great week here! It was everything we thought it would be and more. The views were great! Couldn't have asked for a better vacation, just made it all the harder to leave and come back home.
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Bold Oceanfront with Breathtaking Views from our North Cabin

— Property 118009
Bailey Island cottage rental - Bailey Island North Cabin
Studio, Sleeps 3,
Cottage, 1 Bathroom, rural, waterfront, internet access
Rates - per property (USD)
$700 - $850/week
Calendar Updated Sep 28 2009

Property Review

We rented this tiny little cottage on the tip of Bailey Island last summer and had a week of gorgeous sunrises, peaceful afternoons, great food and lots of reading. The cottage is very basic and...
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Bailey Island Beach Cottage

— Property 168335
Bailey Island cottage rental - secluded beach cottage
3 Bedrooms, Sleeps 10,
Cottage, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$200 - $300/night
$1,200 - $2,300/week
Calendar Updated Sep 25 2009

Property Review

This property is perfectly secluded to give you just the privacy one might need on a getaway vacation, yet still has access to the beach. The pool is quite large and has plenty of deck space...
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Beautiful Bailey Island Home near Sandy Beach

— Property 120204
Bailey Island house rental - Welcome to 44 Robinhood Road!
7 Bedrooms, Sleeps 18,
House, 4 Bathrooms, beach, near the ocean, pets considered
Calendar Updated Sep 22 2009

Property Review

Great Traditional Maine Vacation Home. Fantastic for the kids, nice safe quiet location. Loved the yard,front porch and great room. Beach was just a short scenic walk, crystal clear water, fun...
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Oceanside Tower Ultimate Comfort Lighthouse View

— Property 112112
Bailey Island house rental
3 Bedrooms, Sleeps 11,
House, 1 Bathroom, 1 Half Bath, beach, near the ocean, garden
Rates - per property (USD)
$1,200 - $1,600/week
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Charming 1876 Restored Lobsterman's Home w/Water Views & Sunsets

— Property 242266
Bailey Island cottage rental - Piazza with water views
2 Bedrooms, Sleeps 3,
Cottage, 1 Bathroom, near the ocean, garden
Rates - per property (USD)
$600/week
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Wake to Sunrise on the Ocean-Now Taking Reservations for 2009

— Property 106396
Bailey Island cottage rental - Looking from road toward cottage and water beyond
4 Bedrooms, Sleeps 7,
Cottage, 2 Bathrooms, rural, waterfront, parking
Calendar Updated Aug 16 2009

Property Review

It was by far the most enjoyable vacation we have ever had. The view was spectacular, a photographers dream come true. We are looking forward to spending another 2 weeks at the cottage!
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Ocean Front, Water Access, Air Conditioned, Large Picture Windows, Private

— Property 140223
Bailey Island cottage rental - Sunset from deck.Harpswell across Portland to left
2 Bedrooms, Sleeps 5,
Cottage, 1 Bathroom, beach, waterfront, pets considered
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Bailey Island; Waterfront House With Spectacular Sunsets and Views

— Property 116191
Bailey Island house rental
4 Bedrooms, Sleeps 6,
House, 4 Bathrooms, garden, terrace
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MaineSail

— Property 7007646h
Bailey Island cottage rental - View to West from MaineSail
4 Bedrooms, Sleeps 7,
Cottage, 1 Bathroom, coffee maker, toaster
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Charming Cottage with Water Views

— Property 114948
Bailey Island cottage rental - View to Cove
1 Bedroom, Sleeps 3,
Cottage, 1 Bathroom, internet access, satellite or cable