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Orrs Island Vacation Rentals

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    Travellers to Orrs Island are booking July dates now. Secure your vacation rental today, and have the perfect trip.
    All 23 Rentals in Orrs Island
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    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....
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    Orrs Island, Maine 04003
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    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...
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    Orrs Island, Maine 04079
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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....
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    Orrs Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming and adorable old farm house located in an ideal spot in Harpswell. Enjoy the charm of this house with built in bureaus and shelving, while still offering the modern comforts of home. Fairhaven farm is located in close proximity to Stover's Point and Mitchell field. Spend the day at either...
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    Orrs Island, Maine 04079
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    About this property
    Looking for a perfect cottage on the shores of Harpswell? Look no further! Come enjoy the Basin Cove Cottage which is a 3 bedroom, 1 bathroom cottage located on beautiful Basin Cove. Although this property is tidal, enjoy being able to swim or bring your own kayak to launch right from the property...
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    Orrs Island, Maine 04079
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    About this property
    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...
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    Orrs Island, Maine 04003
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
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    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...
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    Orrs Island, Maine 04079
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    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...
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    Orrs Island, Maine 04079
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
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    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    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....
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    Orrs Island, Maine 04003
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    This unique, and cozy Log Cabin is located on beautiful Mackerel Cove. Enjoy the rustic feel of a log cabin camp while still being a short walk to the ocean. This very simple log cabin has an open concept that includes the large living room with a fireplace, a dining area and a small but functional...
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    Orrs Island, Maine 04003
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04066
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    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...
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    Orrs Island, Maine 04003
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Immerse yourself in the natural beauty of Casco Bay at this welcoming home in Harpswell, Maine - the town with 220 miles of coastline! You'll have breathtaking ocean views, easy access to the area's best natural sights, beaches, and plenty of activities to enjoy without stressing about city noise...
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    Orrs Island, Maine 04079
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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