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Freeport Cottages

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    Travelers to Freeport are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    30 Matching Rentals in the Freeport AreaView all 68 rentals
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    Freeport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 10 miles of Freeport.
    Charming ocean front cottage in Harpswell1 / 12
    (10)Excellent
    Harpswell
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Orrs Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Harpswell
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Cozy ranch style home, located on a quiet, waterfront peninsula. Enjoy beautiful ocean views from the front of the cottage, and scenic coastal sunsets from the back deck. Walk down to the rocky beach area, which is also a great spot to launch a kayak. Upon entering the cottage there is a lovely...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Orrs Island
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Ocean Front Cottage, Harpswell, ME1 / 20
    (5)Excellent
    Harpswell
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Waterfront
    • Wi-Fi
    • Balcony
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    • Patio
    • Cable/satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 27, 2017
    I wanted a relaxing week on the ocean to read, knit and check out the local restaurants and to do some shopping up the coast. The cottage was perfect. Plenty of deck space for...
    Reviewed June 18, 2017
    Location Location Location!from sunrise to sunset, the view was spectacular! The rocks and the ducks and the birds and the roses along with the changing tides - I was in...
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    About this property
    Ocean front cottage at the very end of picturesque Harpswell Neck. Spectacular 200 degree water views! Watch lobstermen pull their traps from the waterfront deck with outdoor dining (with umbrella) and a fire pit. The pebble beach is only fifty feet away. Come visit this very quiet and private...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Harpswell
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Charming, newly remodeled one bedroom cottage located in the heart of Cundy's Harbor. Sip your morning coffee on the deck that sits right over the water while watching the lobstermen head out for the day. Enjoy the peaceful quality of Cundy's Harbor. Far away from the city life for quiet relaxation...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Lofty Cottage1 / 146
    (1)Very good
    Harpswell
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Yard
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 14, 2017
    A very nice place. It is well decorated. It has a great dock and a wonderful view. Worth a week or more.
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    About this property
    'Lofty' is a two+ bedroom waterfront Maine cottage with second floor loft (hence the name). Don't stay in an old musty cottage! Treat yourself to a newly and fully renovated camp that is ready for your next Maine vacation. 'Lofty' is located on a private, quiet,dead-end gravel road that lends...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Orrs Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orrs Island
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Harpswell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
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    Smoking allowed
    About this property
    This cozy home sits right on the water's edge in Cundy's Harbor. Listen to the tide go in and out on the front deck or even the dock! This home is located at the end of a private road that is perfect for evening walks. Bring your kayak with you on vacation and launch it from your private tidal dock...
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    Location Information
    Harpswell, Mid Coast Maine 04079
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Orrs Island
    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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    Location Information
    Orrs Island, Maine 04003
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orrs Island
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
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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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    Location Information
    Orrs Island, Maine 04003
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Orrs Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orrs Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Grill
    • Wi-Fi
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orrs Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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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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    Location Information
    Orrs Island, Maine 04003
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Orrs Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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...
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    Orrs Island, Maine 04003
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Harpswell
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    About this property
    This is your Maine getaway, the one you have been searching for! Perfect for the couple who want to experience the coast of Maine from the water's edge and not a cramped hotel room. The cottage sits on a large lot with its larger 2 bedroom sister cottage 'Lofty' (VRBO# 165589) about 200 feet away....
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    Location Information
    Harpswell, Mid Coast Maine 04079
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Harpswell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This classic Maine cottage sits in a quiet neighborhood near Stover's Point in Harpswell. Inside is charming with a long living room full of windows to enjoy the view of Stover's Cove. The new deck is the perfect spot to sit and enjoy a cup of coffee while watching the colors of the sunrise or an...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orrs Island
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Orrs Island
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Orrs Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Harpswell
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This charming Ranch style home is private, sunny, and centrally located only 6 miles to Brunswick. Sit on the east facing porch and watch as the boats sail by on their way to the Great Island Boat Yard just up the way! This property has a nice dock to enjoy fishing, swimming or kayaking. The large...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Harpswell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A picture perfect location near the mouth of Lowell's Cove on Orr's Island, enjoy spectacular views out to open ocean and neighboring islands. Wrap around ocean side decks for entertaining or just enjoying a quiet sunny afternoon of taking in the salt air and views. Enjoy the convenient access to...
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    Harpswell, Mid Coast Maine 04066
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Harpswell
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Secure Parking
    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Schooner Landing! This four bedroom, waterfront home is situated in a sparsely populated, quiet location with a spectacular view of Harpswell Harbor and Casco Bay. The home sits on a cozy lot that overlooks wide panoramic views of Harpswell Harbor, Stover's Cove, the Cribstone Bridge and...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Harpswell
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 2500 square foot post & beam home boasts admirable finishings and impressive craftsmanship. This spacious home offers a place for everyone to retreat to, while still enjoying the luxury of vacationing as a group. Numerous decks and balconies, as well as walls of windows and sliders bring the...
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    Harpswell, Mid Coast Maine 04079
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orrs Island
    3 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    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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    Location Information
    Orrs Island, Maine 04066
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 7
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    South Freeport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Central Heating
    • Washer
    • Waterfront
    • Balcony
    • Ocean Views
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is a completely separate rental cottage on the property and other travelers may be present during your stay. ** Find the quintessential 'Downeast' Maine experience at 'Heron Cottage,' a 1-bedroom, 1-bath vacation rental cottage, overlooking the picturesque Harraseeket...
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    South Freeport, Maine 04078
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    South Freeport
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Terrace
    • Balcony
    • Washer
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Please note that there is a completely separate rental cottage on the property that may have guests present during your stay. ** Enjoy the coastal town of South Freeport from 'Osprey Cottage,' a 2-bedroom, 1-bath vacation rental cottage that sleeps 4! Located on Casco Bay, this cozy home is...
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    South Freeport, Maine 04078
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Harpswell
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Have an authentic New England experience by staying in this vibrant cottage right on the edge of the ocean. With room for 8 guests across 3 bedrooms and 1 bathroom, charming in-home amenities, picturesque views, and a wonderful location on Stovers Cove, this exceptional vacation rental cottage is...
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    Location Information
    Harpswell, Mid Coast Maine 04079
    Rental Home - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Portland Intl Jetport
    18.1 miles from Freeport
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