Picture your first day on your Bailey Island vacation....... Sleep in and rise to the sound of sea gulls catching their breakfast as lobster boats head out of Mackerel Cove. Take your coffee and newspaper out to your adirondack chair perched above your shared pebble beach 20 steps below. Thinking...

Looking for endless ocean views? Look no further! Enjoy being perched above the landmark Giant Stairs Trail while still having some privacy and the peacefulness of listening to the waves crash along the shore. This three bedroom, one and a half bathroom recently renovated cottage is the perfect...

Take a step back in time when you walk into this early 1900's cottage that has been revamped to allow you the comforts of modern day living. A newly decorated and finished kitchen is bright and cheery with views of the ocean while you cook up your favorite lobster dish. Enjoy the open concept as...

Picture your first day on your Bailey Island vacation....... Sleep in and rise to the sound of sea gulls catching their breakfast as lobster boats head out of Mackerel Cove. Take your coffee and newspaper out to your Adirondack chair perched above your own pebble or sand beach 20 steps below....

This wonderful Turn of the Century New England style cottage sits on the waters edge at the mouth of Little Harbor with sweeping Southeasterly views. Listen to the waves lapping against the ledges that are just a stones throw from the sun filled deck. This cottage was restored to bring back all the...

Available for the first time for rent, Sea Birch Cottage is set on an open beach in South Harpswell, off a private road. It has sweeping views across the Merriconeag Sound to Orr's and Bailey Islands. This contemporary escape offers the best of Harpswell and all the right touches to make your...

Tide Watch is is a lovely 2 bedroom, 1 bathroom cottage located on beautiful Basin Cove. Enjoy the waters edge deck with outdoor dining table and chairs. As you enter the house into the spacious family room complete with many board games, there is a bedroom to your right with a twin bed and set of...

The Sea Salt Cottage is a charming and comfortable 1905 Vintage Seasonal cottage located on quiet, peaceful, picturesque Bailey Island, Maine. Facing due East, you can enjoy the sunrise, watch the lobster boats, or enjoy the sound of the crashing surf while relaxing on the covered front porch. The...

This lovely New England style cottage is situated on a dead end road in a great Bailey Island neighborhood! This house does not have water views, but what it lacks in views it makes up for with its great location for exploring the island on foot, such as the Giant Stairs walking path where you can...

A very new and charming cozy cottage. Centrally located on the Island at the end of Steamboat road. Shared pebbly beach frontage just steps away from the deck with beautiful south westerly sunset views. There are chairs provided to sit on the beach and soak up the sun and salt air. Watch the...

Looking for the perfect place to watch the sunrise with a nice warm cup of coffee oceanside? Look no further! The Seaside Sunrise Cottage is a newly renovated cottage just waiting for you. Located on Harpswell Neck this cottage is just a five minute walk to one of the only public beaches in...

The house is close to the beautiful water with an amazing ocean view from our front patio and walking access. With westerly views over Harpswell Sound enjoy the sunsets with Mt. Washington in the back ground on a clear night. The cottage is bright and cheery with a great deck that overlooks the...

This 3 bedroom, 2 bathroom home is tucked over the hill along the rocky western shore. Enjoy sunsets from the expansive deck complete with screened in porch. There is a well maintained path to the rocky shore where you can look out past Mark Island Monument and into Mackerel Cove. The HUGE yard...

This spacious and sunny garage apartment is located at the edge of crashing surf in Little Harbor. Beautiful and Bold southeast views. Enjoy sunrises or watching the working fishing boats as you listen to the crashing surf. The deck and apartment sit up high perched over all surrounding building...

The 'Abner Point House' is situated at the end of Abner Point on Bailey Island. Offering AMAZING water views of Mackerel Cove to the East, Open Ocean to the South, Harpswell Sound, and Mt. Washington to the West. This property sits on 1.3 acres and affords plenty of outdoor space. Enjoy paths to...

Bring the kids with you to this family-friendly cottage located on beautiful Bailey Island. Enjoy easterly views while you picnic on the upstairs deck with comfortable outdoor furniture. Let the kids take in the salty sea air in the large yard and visit nearby Cedar Beach just a short walk away....

This studio garage apartment is located on Harpswell Sound, offering beautiful sunset views and steps to the rocky shore. There is a full kitchen, dining room table and 2 cozy chairs in the studio apartment. The open concept living space has a new queen size futon, a full bathroom with a stand up...

Enjoy the Central location of this cottage, and its beautiful Easterly views of the Ocean. Only a short walk to the beach. The right of way is to a small rocky area and stone beach. Cedar beach is also within walking distance. The Deck has a roll out canopy for shade. This cottage has living space...

Beautifully situated on beautiful Basin Cove, this peaceful cottage is ideal for outdoor living with an abundance of surrounding wildlife to enjoy. The location is the perfect setting for sunset gazing from your deck, swimming, kayaking or paddleboarding. Inside, you'll find bedroom windows with...