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Elder Access Holiday Rentals in Squirrel Island

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    20 Matching Rentals in the Squirrel Island AreaView all 112 rentals
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    The following rentals are within 10 kilometres of Squirrel Island.
    LOG HOME | SECLUDED | SLEEPS 10+ | MEADOW COVE1 / 15
    (11)Very good
    East Boothbay
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Boothbay Harbor
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    New England 1890 House with part water view1 / 15
    (2)Excellent
    Boothbay Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Boothbay Harbor
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Secure Parking
    • Private Garden
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The tiny house cottage is very well appointed using a nautical theme. There is a half bath in the cottage. Then a few steps away is the enclosed kitchen and shower. Parking is very convenient and the shore, dock and kayaks are within site of the tiny cottage. Walking to the town center,...
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    Boothbay Harbor, Mid Coast Maine 04538
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Maine Cottage, Mid-Coast Maine1 / 14
    (2)Very good
    South Bristol
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • DVD Player
    • Porch
    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 August 2014
    The cottage is located in a quaint, quintessential Maine community. It is a pretty, sleepy town with limited resources, but you can find anything you might need in the three...
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    About this property
    Cottage overlooking picturesque harbor in the authenic Maine community of South Bristol. Perfect for small family or couple who enjoy waterviews and easy access to provisions and fresh lobster. Good location for walks to lobster co-ops, picnic spots, and Christmas Cove, as well as short drives to...
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    South Bristol, Mid Coast Maine 04568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Year-round Cottage, Half-Moon Cove, Damariscotta River - a kayaking paradise1 / 24
    (1)Excellent
    South Bristol
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Waterfront
    • Washer
    • Grill
    • Patio
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2017
    This area of Maine is arguably the nicest in the state. The "Mahogany cottage" is one of the most beautiful places that I've stayed. The water views with a fire...
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    About this property
    Living room with sofabed + 1 bedroom, 2 bathrooms - sleeps 4 in utter comfort Located on the Pemaquid Point Peninsula, our Mahogany Cottage is designed like a boat's interior with exposed mahogany beams and extraordinary detail. Two fireplaces, living room, kitchen, one bedroom and two bathrooms....
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    South Bristol, Mid Coast Maine 04568
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Boothbay Harbor
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Cable/satellite TV
    • Grill
    • Washer
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you are looking for a picture perfect Maine getaway for a large number of people, you have found the place. At the head of Linekin Bay sits the little village of Bayville. Founded in 1911, the mostly summer community is a step back in time with its own post office, community dock, tidal beach,...
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    Boothbay Harbor, Mid Coast Maine 04538
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    Boothbay Harbor
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Porch
    • Ocean Views
    • DVD Player
    • Washer
    • Grill
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Maine Home is located on a beautiful stretch of Maine's mid-coast area. Conveniently located in Boothbay minutes from Boothbay Horbor , the house is set in a very private area,on a dirt waterfront road. The custom built Post and Beam home is an ideal vacation home for a family or a couple...
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    Boothbay Harbor, Mid Coast Maine 04537
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    East Boothbay
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Central Heating
    • Wi-Fi
    • Washer
    • DVD Player
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Cotttage is located on Ocean Point, Maine. It is near Grimes Cove Beach where you can swim, sail, kayak or just enjoy the view. In the evenings, take a walk, enjoy the stars and the cozy up to a fire. It's up to you ! Great place for a family getaway or couples retreat, just bring yourself...
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    East Boothbay, Boothbay 04544
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    East Boothbay
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Waterfront
    • Ocean Views
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacous ocean front cottage in a stunning New England setting on Linekin Bay. Sloped lawn offers stairs that go directly into the ocean. Tidal pools within a few steps, and public dock 300' away. Great area for sailing, fishing, kayaking, and snorkling. Gorgeous views and RIGHT on the water! Only 5...
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    Location Information
    East Boothbay, Boothbay 04544
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    East Boothbay
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful Ocean Point Cottage! This charming cottage, rarely rented, is privately located at the end of a long driveway, yet is walking distance to the activity center and tennis courts. It has a beautiful ocean view from its wrap-around deck as well as from the living room and master bedroom....
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    East Boothbay, Boothbay 04544
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Boothbay Harbor
    4 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Parking
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic updated saltwater farmhouse on Southport Island, with 1.4 acres of private lovely grounds, gardens, stone walls, and a child's playhouse, all surrounded by trees. Waterfront on Decker Cove. Private dock with a double kayak provided. Large back deck with gas grill, dining table and chairs,...
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    Boothbay Harbor, Mid Coast Maine 04576
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 5
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    Back Bay Cottage - Portside: Luxury Condo on Water1 / 12
    (16)Excellent
    Boothbay Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Waterfront
    • Washer
    • Sauna
    • Central Heating
    • DVD Player
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 June 2017
    Beautiful condo. Abigail has thought of everything you could have possibly needed away from home on your vacation. The location is perfect and we could not have been more...
    Reviewed 2 March 2017
    We enjoyed a week at Portside so much last summer that we decided this would be the perfect place to celebrate our 38th wedding anniversary in February. We took champagne and...
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    About this property
    Portside is a year-round luxury condo with the charm of a cottage in the heart of historic Boothbay Harbor, Maine. The cottage is in the town center and yet you will find tranquility and privacy inside. We share a dock and float with the other two Back Bay Cottage units and have our own deck on the...
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    Boothbay Harbor, Mid Coast Maine 04538
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront Condo in Boothbay Harbor1 / 27
    (3)Average
    Boothbay Harbor
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Waterfront
    • DVD Player
    • Washer
    • Central Heating
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 September 2013
    We spent a week in August at this property, We enjoyed the ability to walk to the shops and for meals to the local restaurants just a short distance away. Absolutely loved the...
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    About this property
    Beautiful oceanfront property at the head of the harbor. Bright open concept kitchen/living/dining room with abundant natural light. Two cheery bedrooms, with nautical themes and one convertible sofa sleep up to six. One and a half baths include a new stackable washer and dryer. A balcony off the...
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    Boothbay Harbor, Mid Coast Maine 04538
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Boothbay Harbor Pet-Friendly High-Tech House Lake Access Near Ocean1 / 27
    (45)Excellent
    Boothbay Harbor
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Housekeeping Included
    • Wi-Fi
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2017
    Sunny Woods was spacious and well maintained, with many amenities you wouldn't expect in a rental. The owners were very helpful and accommodating as well. My golden retriever...
    Reviewed 2 September 2017
    My wife and I rented the house for an extended time during a house remodel. I can't say enough about the owners hospitality. The house was perfect for our needs and the grounds...
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    About this property
    At Sunny Woods House everything on one level, The living and dining space, kitchen, dedicated office, media room, bedrooms and 2 full bathrooms all flow from one to the next—no stairs! You will find everything you'd expect to find in a modern year-round house: fully-equipped kitchen (including a...
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    Boothbay Harbor, Mid Coast Maine 04538
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bayville
    6 Bedrooms, 3 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At the head of Linekin Bay, 'The Mooring' is an eighteen-nineties shingle-style masterpiece overlooking a private dock and swimming area. The southern exposure of its wrap-around covered porch offers 270 degree views of the bay below. The Mooring's generous accommodations make it an ideal vacation...
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    Bayville, Mid Coast Maine 04538
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 16
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    Boothbay Harbor
    4 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Parking
    • Balcony
    • Ocean Views
    • Wi-Fi
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly Listed! This charming one floor cottage sits on McKown Point in Boothbay Harbor. Located only 2 1/2 miles from the center of town, the Caboose Cottage is a perfect vacation spot. The living/dining room has a cathedral ceiling, fireplace and french doors. Enjoy the large gated deck on three...
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    Boothbay Harbor, Mid Coast Maine 04538
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 7
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    South Bristol
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Ocean Views
    • Central Heating
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Peace and privacy await you at this Mid-Coast Maine retreat --a 9-acre private peninsula into the tidal Damariscotta River surrounded by over 75 acres of conservation land. Out the door, you have trails through acres of secluded woods, a waterfront with dock, canoe, kayaks, deep-water mooring,...
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    South Bristol, Mid Coast Maine 04568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Boothbay Harbor
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This house is a 2 floor, open floor plan with a full walk out basement. It has a living room, dining room and full kitchen. The very large porch and open deck are a bonus. Both are great for reading cocktails breakfast and relaxation. we have a small association beach with a swim float and dock....
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    Boothbay Harbor, Mid Coast Maine 04537
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Boothbay Harbor
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Private Garden
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly listed! Hawk's Nest is a beautiful in town loft and is basically brand new! All rebuilt and updated with a gourmet kitchen and a view of Mill Cove. A separate entrance allows for privacy. The loft is located on the second floor. Outside you will find a lovely sitting area overlooking the...
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    Location Information
    Boothbay Harbor, Mid Coast Maine 04538
    Condo/Apartment - 1 Bathroom, Sleeps 2
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