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Chebeague Island Vacation Rentals

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    All 90 Rentals in Chebeague Island
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    The following rentals are within 10 miles of Chebeague Island.
    Couples cottage at the head of Mackerel Cove with views to Mt. Washington.1 / 22
    (1)Excellent
    Orrs Island
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Large Home Walk to Beach! Close to all amenities!1 / 26
    (11)Very good
    South Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Charming farmhouse with premier location1 / 19
    (1)Very good
    Orrs Island
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Goose Cove - Spacious Water Front with Stunning Views, 5 Bed, 3.5 Bath1 / 12
    (1)Excellent
    Freeport
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 9, 2018
    This Goose Cove home is beautiful. Twelve members of our family ranging in age from 11 to 60-plus thoroughly enjoyed our stay. Steve and Debbie have taken care of all amenities...
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    About this property
    Vacation Rental, Spacious Water Front Property with stunning views of Maquoit Bay, Freeport Maine (Greater Portland and Casco Bay area) Spacious home with lots of upgrades, located on 6 acres - quite solitude, great for family vacations. This furnished water front home can comfortably...
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    Freeport, Maine 04032
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    WILLARD BEACH with OCEAN VIEWS ~ 100 yds to beach!1 / 72
    (3)Excellent
    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Private Yard
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 31, 2017
    My husband and I visited in late October from the Houston area. We were looking for a change of pace and East Coast charm and were not disappointed. The house was located in a...
    Reviewed June 18, 2017
    My husband, sister, two teenagers, and I stayed for 10 days in May. We loved it so much, we didn't want to leave. The cottage is beautifully decorated, with views of Casco...
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    About this property
    BRAND NEW TO MARKET! Accepting winter thru fall reservations now. Beautifully renovated 3 Bedroom, 1.5+ bath turn-of-the-century seaside home features beautiful views of the Portland shipping channel and the islands of Casco Bay and is just 100 yards to Willard Beach. Sleeps 7-9. This...
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    South Portland, Maine 04106
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    Dramatic Oceanfront Home on Casco Bay1 / 21
    (1)Excellent
    Freeport
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Washer
    • Central Heating
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2016
    The pictures of this home attracted our attention, and they are exactly what you will find. Then there is more. Betsy and Gar have created a vacation home that appeals on many...
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    About this property
    Sunrise or moonrise, it's your choice! Sip your coffee or wine while you sit on the patio of this spectacular waterfront home. You will be treated to an ever-changing natural drama from this recently built home on Flying Point overlooking Casco Bay. Herons, gulls, and other sea birds share the...
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    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Portland, Maine - East End Rental1 / 11
    (30)Very good
    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Outdoor Dining Area
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 8, 2017
    Apartment was clean, comfortable and nice for our stay. The location was convenient to restaurants, pubs and other attractions in the city. we were able to walk to everywhere...
    Reviewed August 23, 2017
    We had a great girls weekend on the third floor of the East End rental. The house was so clean and spacious and was in walking distance (a mile) of the downtown area. Thank you...
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    About this property
    Visit Portland, Maine!!! We offer a newly renovated, quirky, third floor, 2 flight walk-up, 3-bedroom, living space for weekly rentals. There are two bathrooms - one bath (vintage tub plus separate shower) and second half bath is off front bedroom. East end - Congress Street, foot of Munjoy Hill,...
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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Majestic Garden Condo Featuring Private Outdoor Space Downtown/West-End Portland1 / 19
    (6)Very good
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Private Yard
    • Washer
    • Air Conditioning
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2018
    This little cozy cottage was perfect for me and my wife. It was very clean and comfortable with a full kitchen. We walked to everything and never had to use the car to get...
    Reviewed January 5, 2018
    Great find in the West End with easy access to a ton of restaurants and attractions! This neighborhood is beautiful, definitely one of Portland’s finest! The condo is tucked...
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    About this property
    This magnificent California style, private condo is located in the heart of the West End of Portland, couple blocks from the heart of Downtown and The Old-Port, walking distance to anywhere around galleries, restaurants, coffee shops, pubs, microbreweries, retails stores, and the museums. Stay at...
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    Portland, Maine 04101
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Old Port! Right in the heart of the Old Port near everything! The unit has luxurious linens, a full kitchen, TV, Roku, WiFi, games, books, coffee, an espresso maker, soap, shampoo, conditioner, hairdryer, iron and so much more. PLEASE, note, this unit is absolutely amazing, however,...
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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Orrs Island
    2 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
    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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    Long Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Ocean Views
    • DVD Player
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come spend time in a lovely sea side home. The ocean views from almost every window are sure to relax during your visit. Our 3 bedroom home provides a full bathroom upstairs and a large full bathroom on the first floor with laundry. There is a spacious kitchen with high ceilings, skylights, and...
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    Long Island, Maine 04050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront Cottage in Freeport1 / 23
    (1)Excellent
    Freeport
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • DVD Player
    • Patio
    • Private Yard
    • Wi-Fi
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 28, 2017
    We just returned from this awesome home. There were 6 in our party a family affair ages from 40-81. There was an awesome view of ocean, great location, and plenty of shopping if...
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    About this property
    This charming four bedroom cottage features 350’ of unobstructed ocean views toward Casco Bay and the islands, located just 5 miles from Freeport's hundreds of outlet stores and restaurants, and just 30 minutes from Portland. The cottage is set just 75 feet from the shoreline, with ocean views...
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    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2BR / 1B - Willard Beach -- South Portland1 / 31
    (3)Very good
    South Portland
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
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    • Washer
    • Patio
    • Private Yard
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 7, 2017
    Portland has such an easy going vibe, and that carried over to this great rental in South Portland. Just a 5-10 minute walk to Willard Beach (15 min if you stop for ice cream...
    Reviewed September 2, 2016
    The apartment is well equipped and clean and has a real beach house feeling even when its not on the beach. The hosts are very friendly and helpful.
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    About this property
    Minimal And Clean - Ready For Travellers This second floor apartment - with its two bedrooms, one bathroom, kitchen, and more - offers plenty of space for up to four guests. Minimal, clean, and carefully appointed with traveller necessities. Guests have access to two off street parking spots, all...
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    South Portland, Maine 04106
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Freeport
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Washer
    • Patio
    • Central Heating
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This bright and spacious, comfortable home offers sweeping ocean views from nearly every window. Two master bedrooms at opposite ends of the house makes it ideal for two couples - with or without children. Set on a beautiful, forested 5 acre lot near one of Maine's most popular state parks, and...
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    Freeport, Maine 04032
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Parciak house is located at the mouth of Lowell's Cove on Bailey Island with sweeping westerly views of Casco Bay, and magnificent sunsets! There is a fabulous pebbly beach a stones throw from the house perfect for swimming or kayaking.This newly constructed home offers spacious and sun filled...
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    Orrs Island, Maine 04003
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Orrs Island
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • DVD Player
    Suitability
    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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
    Kid friendly
    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
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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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    Willard Beach Get Away - Dog Friendly1 / 13
    (1)Excellent
    South Portland
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 17, 2017
    Great location for visiting all the Portland sights. Located in a quiet section of South Portland just one house from the beach. The owner was friendly and helpful at all stages...
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    About this property
    Perfect for a Maine summer vacation. This completely renovated, 400 sq foot studio apartment is one house away from Willard Beach, 4 blocks to Willard Square, 1 mile from downtown South Portland, and a 5 minute drive to downtown Portland, ME. The apartment has a full bath, a kitchenette, air...
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    South Portland, Maine 04106
    Condo/Apartment - 1 Bathroom, Sleeps 3
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    Freeport
    6 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW: Sweeping Ocean Views from Three Suites, Private Swimming Cove and Dock. Available for weekly rentals (Sun-Sun) in summer and fall and 3+ day rentals off-season. Gather your family and friends for an authentic Maine vacation to remember. This gorgeous country home sits on 1,000+ feet of...
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    Freeport, Maine 04032
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 10
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    Orrs Island
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Orrs Island
    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Orrs Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
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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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    Location Information
    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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    • DVD Player
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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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    Portland
    5 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Entire 2nd and 3rd floors of a Duplex. I promise it will be comfy, clean and adorable. A quick reminder that this is a second floor apartment with hardwood floors. You will have to be considerate of the people on the first floor. The yard is great but I cannot have parties at all. This is not that...
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    Portland, Maine 04103
    Condo/Apartment - 5 Bedrooms, 1 Bathroom, Sleeps 10
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    Orrs Island
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Pet friendly
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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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    South Portland
    3 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My home is brand new and was completed at the end of the Summer in 2015. I designed and furnished the home with a lot of thought, attention to detail and aesthetic appeal. Floors are hardwood and Carrara marble in two baths and Brazilian black slate in the half bath. There are 3 bedrooms and 2...
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    South Portland, Maine 04106
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 4
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    Portland
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    About this property
    1,400 SF of Living Space with a Fenced back yard Fantastic space with high ceilings, modern kitchen and room for 8. Washer & Dryer on site, close to all things Portland without being directly in the bustle of downtown. Great for families with dogs or folks in town for all of the amazing music...
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    Portland, Maine 04103
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 8
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    Orrs Island
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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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    South Portland
    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Balcony
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautifully renovated house was stripped down to the studs for a full-scale renovation. Beautifully designed and completely renovated by a highly recognized designer, the house retains the original 1906 Dutch Colonial charm, but was creatively reimagined for today's open-concept and luxurious...
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    Location Information
    South Portland, Maine 04106
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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    Falmouth Foreside Maine Contemporary Cottage Home - indoor lap pool, roof deck1 / 29
    (1)Terrible
    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Indoor Pool
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    Pet friendly
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    About this property
    5+ Bedrooms, 3 Full Baths Sleeps 10-14 Just up the hill from one of the largest mooring harbors on the East Coast, and across the street from Maine's most famous General Store is this newly completed property designed and built by one of New England's up and coming Architects. Featuring and...
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    Falmouth, Maine 04105
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bailey Island
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    About this property
    This lovely seaside cape is located near the end of Bailey Island, on the western shore. Enjoy spectacular sunset views of Mt. Washington from your doorstep and rocky shore frontage, complete with a waters edge deck. Watch the lobstermen go in and out of Mackerel Cove throughout the day. A fully...
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    Bailey Island, Maine 04003
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Enjoy Sweeping Waterfront View, Watch Lobster Boats from Porch1 / 11
    (1)Excellent
    Peaks Island
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 20, 2018
    This property was an absolute fantastic place to enjoy a relaxing week on Peaks Island. We rode bikes all around the island, and I don’t think I spotted a better view. The...
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    About this property
    THE COTTAGE IS CLOSED FOR THE WINTER MONTHS. PLEASE INQUIRE ABOUT THE 2018 SEASON THAT BEGINS IN MAY! Our spacious but cozy family cottage is located on a quiet shorefront road, just a few yards from the water with an uninterrupted view of Josiah's Cove and then across the sparkling sea 'all the...
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    Peaks Island, Maine 04108
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Bailey Island
    7 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    About this property
    The historic Captain York House has been on Bailey Island for more than 100 years. It has expanded into a 7 bedroom, 6.5 bathroom house that can accommodate families, large groups and family reunions. This house provides a great home base for exploring Bailey Island and the surrounding coastal...
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    Bailey Island, Maine 04003
    Rental Home - 7 Bedrooms, 6 Bathrooms, Sleeps 14
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    Yarmouth
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    In the heart of Yarmouth, Mill Reach offers the perfect setting for a great holiday, with off-street parking for one car. Relax in the modern open plan living, kitchen and dining area which is furnished to a high standard throughout. The living area leads out onto the private decking area perfect...
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    Yarmouth, Maine PO40 1TW
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 BR 1.5 BA COTTAGE WITH WATER VIEWS OF CASCO BAY1 / 13
    (1)Average
    Peaks Island
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Pet friendly
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    Reviewed August 19, 2016
    This cottage is in a wonderful walk to beach location and close to ferry in sweet little Peaks Island. The owners seem to be very nice and generous with information. The...
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    A BEAUTIFUL WATER VIEW OF CASCO BAY OFF THE COAST OF PORTLAND IN THIS 3 BR / 1.5 BA COTTAGE NEWER KITCHEN WITH GRANITE COUNTER TOPS, FULL SIZED DISHWASHER AND 6 BURNER COMMERCIAL GAS OVEN. THE KITCHEN ALSO HAS A LARGE AMOUNT OF POTS, PANS, KITCHEN GADGETS AND LOTS OF PLATES AND SILVERWARE. Island...
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    Peaks Island, Maine 04108
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    Falmouth
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Housekeeping Included
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    • Waterfront
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    • Mountain Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Please note: Our checkin time is 3pm and checkout is 11am, but we can often accommodate other arrangements! Andy's Retreat is a comfortable, spacious and convenient home-base to relax and explore Portland & Coastal Maine. We're located right off Exit 53 of the Maine Turnpike, just 15 minutes...
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    Falmouth, Maine 04105
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Bailey Island
    4 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Smoking allowed
    About this property
    Magnificent renovated 19th Century Stone and Shingle Cottage overlooking Casco Bay retains historical atmosphere while having modern amenities. The home is located at the dead end of a road and is surrounded by lush grass, trees and ocean. Past tenants state that 'their stresses left them for the...
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    Bailey Island, Maine 04003
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 7
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    Bailey Island
    3 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    About this property
    Enjoy this picturesque Bailey Island setting on 2.06 acres and 199’ frontage on Maine’s rocky coast. Completely renovated in 2006-07 this Shingle Style oceanfront home possesses superior craftsmanship inside & out overlooking Casco Bay. Feel free to contact us with any questions....
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    Bailey Island, Maine 04003
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 10
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    Falmouth
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    Adorable, quaint and ideally located Maine Beach cottage. Fully furnished with updated furniture, comfortable beds, and all the necessary amenities. Steps from private beach - bring your kayak, paddleboard or other water craft or just relax and watch the sailboats on the Bay and go fishing from the...
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    Falmouth, Maine 04105
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    Portland
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful, newly renovated bungalow in the WIllard Beach neighborhood is the latest creation of the well-known and highly respected SoPo Cottage team! Completed in August 2016, It is now being offered for the first time as a vacation rental home. This beautiful home is comfortable for 2...
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    Portland, Maine 04106
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    Portland
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    About this property
    Welcome to Old Port. Staying here will put you right in the middle of all the action. The unit screams Portland with all of its character which includes exposed brick throughout, wooden beams, urban style lighting, and art. PLEASE, note, this unit is absolutely amazing, however, it is located in...
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    Portland, Maine 04101
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    Classic, cozy family cottage with modern amenities and ocean view from porch1 / 20
    (2)Excellent
    Peaks Island
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2018
    Woody and Comfort’s house is fantastic. One of the best porches around. Eat your lobster dinner outside on the porch looking at the ocean. This home had a super kitchen as well...
    Reviewed September 19, 2018
    The cottage was utterly perfect, and all that a Maine cottage should be...from the outdoor shower, to the fireplace, to the surprisingly comfortable wicker furniture, to the...
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    About this property
    We close up the cottage during the winter months. Please inquire about rentals May 1 - Columbus Day. The house is simply but completely furnished and colorfully decorated, for family use, not as a 'rental property.' Virtually everything in the cottage has some sentimental value, having been either...
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    Location Information
    Peaks Island, Maine 04108
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Portland
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Why stay in a hotel when you can enjoy a fully equipped 500 square foot apartment in downtown Portland for half the price? North Street is often regarded as the one of the nicest streets on the 'Hill' and you will not be disappointed in this compact but well equipped urban apartment with driveway...
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    Portland, Maine 04101
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Orrs Island
    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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Bailey Island
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    About this property
    Looking for a rustic Maine cottage? Look no further! This three bedroom cottage has all the charm you are looking for while still giving you modern day amenities. Enjoy great views of scenic Mackerel Cove from the covered porch. This turn-of-the-century cottage keeps its charm with wood-paneled...
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    Location Information
    Bailey Island, Maine 04003
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Freeport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    Stunning water views await at this 1BR cottage situated mere minutes from downtown Freeport shopping and dining. Launch a kayak from your backyard, dine al fresco on the oceanfront deck, and spend quiet evenings by the wood-burning fireplace. Traveling with a larger group? Reserve this cottage...
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    Freeport, Maine 04032
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Portland, ME - East End Garden Suite1 / 6
    (2)Average
    Portland
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
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    • Shared Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2014
    We stayed here for 3 days while in Portland. The apartment was fairly clean and we were about a eight to ten minute drive from downtown. We didn't have very many options because...
    Reviewed October 25, 2013
    Very nice, cute, and tasteful, yet simple, first floor apartment in a great location. Plenty of space and natural light with separate rooms, versus open design, which I found to...
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    About this property
    Visit Portland, Maine!!! We offer a sweet, quirky, first floor, 1-bedroom, one bath (vintage tub with shower) living space for weekly rentals. East end - Congress Street, foot of Munjoy Hill, city side, (near Otto's Pizza Cafe) great area!!! Very sunny, non-smoking building with courtyard access! A...
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    Location Information
    Portland, Maine 04102
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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