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Vacation
Rentals
Vacation to the stunning
island of Islesboro.
Delightful Up Island Cottage
3 Beds
2.5 Baths
House
0
$2,000 /week
0
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Delightful Up Island Cottage. Pristine appointment and living space on a corner lot. Escape to your tranquil island getaway. Located just off the midcoast, iconic Islesboro, Maine offers stunning natural beauty yet all the essentials are available at local markets - including fresh catch off the local lobster boats! Your gorgeous 3 bedroom 2.5 bath home away from home is comfortable and cozy, with a natural driftwood deck overlooking your private pond.
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The Anchorage
4 Beds
2 Baths
Home
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$4,000 /week
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The Anchorage - a historic private family enclave perched on a peninsula at the end of quiet Hewes Point Road while conveniently near to town amenities. Breath-taking panoramic ocean views, private sandy beaches and bold rocky shoreline. Exquisite sunrises and moonrises.
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West Bay Contemporary First Row
3 Beds
2 Baths
House
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$1,200 /week
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West Bay Contemporary First Row. Three bedrooms, two full baths, open concept kitchen/dining/living room, solarium, spiral stair, large sunny deck all on 16 acres of field and woods AND with its own beach access across the road.
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Parker Cove
6 Beds
3 Baths
2
$2,500 /week
2
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Parker Cove overlooking expansive meadows, woods, and East Penobscot Bay neighboring Blueberry Fields Preserve. Traditional living, dining, kitchen, wide porch, screened porch, laundry. Path to shore or drive to Point Comfort beach and park.
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Foxglove Cottage
11 Beds
3 Baths
House
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$4,000 /week
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Foxglove Cottage. Spectacular location for this welcoming and elegant post and beam home with gravel beach and wonderful water views. Entry, kitchen, dining, living room with fireplace, decks for morning coffee or afternoon tea and cocktails. Ideal for four couples.
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Sterling View
4 Beds
1 Bath
4
$5,000 /month
4
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Sterling View on Islesboro's West Side. Cunning getaway private but handy to town on a country lane. Three bedrooms, living room pull-out, one bath, laundry. Charming kitchen, sun porch with two acres of meadow.
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Historic Hewes Point Home
3 Beds
2 Baths
2
$12,000 /month
2
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Historic Hewes Point Three-bedroom, Two-bath Waterview Home. Situated in a cherished summer island enclave. Perfect for strolling with no through traffic. Public beach access across the road. Completely renovated to highest standard. Large porch dining.
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Meadow Pond 1850's Greek Revival
2 Beds
1.5 Baths
House
2
$1,500 /week
2
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1850's Greek Revival Completely Renovated 1992, historic detail preserved on Islesboro's largest pond. 4.5 acres on pond with sweeping views and lovingly landscaped meadow.
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Dark Harbor Village Home
2 Beds
2.5 Baths
Home
2
$1,800 /week
2
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Two-Bedrooms, 2.5 bath, living room, second living room offers a futon, open concept kitchen-dining room, lovely covered porch. Amenities include mooring, kayaks, and raised garden beds for your green thumb and fresh veggies. Walk to shops for ice cream and sundries.
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Foxglove 19th Century Farm
4 Beds
3 Baths
House
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$4,000 /week
0
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Welcome to Foxglove Farm, a beautiful and historic family escape on over 22 acres of pristine land boasting meadows, mixed growth forest, creeks, a pond and a picturesque path to 1500 ft of shore frontage with the island's best clamming grounds.
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Quaint Boathouse
1 Bed
1 Bath
0
$7,000 /month
0
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Quaint boathouse with kayak or canoe access from its side yard and stunning front porch views of sunset over the Camden hills. Appointed in comfortable French Country style and features every amenity for a memorable and relaxing stay. One bedroom, two beds, one bath.
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Fish Hawk
3 Beds
2 Baths
House
0
$4,000 /week
0
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The ultimate in peace and quiet on Penobscot Bay. A labor of love from its inception to the present, Fish Hawk was designed by its Harvard Design School Graduate/Professor owner and provides an escape to the finest of Maine's legendary coastal beauty and tranquility - the ultimate for kicking back and just letting the beauty that surrounds you carry you through the day.
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Waterfront Bungalow
2 Beds
1 Bath
0
$12,000 /month
0
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A beautiful bungalow cabin on the water with French Country decor to welcome your stay. Ideal for a peaceful and serene getaway. Two bedrooms, three beds, one bath.
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Classic Ryder Cove Cottage
5 Beds
House
0
$4,000 /week
0
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Classic Ryder Cove Cottage. At waters edge with exceptional views over the cove, recently refurbished, five bedrooms, kitchen, pantry, dining room, living room, covered porch, finely crafted period wood paneling. Steps to the shore.
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Green Cot, Ryder Cove Guest House
2 Beds
2 Baths
House
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$1,500 /week
0
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Just across the lane from Seaside Cottage with two bedrooms, two full baths, loft bedroom, kitchen, vaulted living/dining room, covered porch. Well appointed, great space. Located in quiet summer enclave. Dock access.
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Charming Little Broad Cove
3 Beds
1 Bath
Home
0
$2,100 /week
0
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Charming Little Broad Cove Waterfront Home at water's edge and grand easterly bay views from the living room and deck. Three bedrooms, one bath, kitchen island.
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Rebel Hill Log Home
2 Beds
1 Bath
House
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$1,200 /week
0
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Private yet central and convenient island location. Two bedrooms; queen and double, full bath and washer-dryer, cathedral ceiling living room and kitchen, franklin-style wood stove for the fireplace feel. High-end finishes and amenities; flatscreen tv, internet, hardwood floors and carpeted bedrooms, pull-out sofa.
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Ryder Cove Cottage.
3 Beds
4.5 Bath
Cottage / Cabin
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$1,500 week/cottage or $600/cabin or $1,800 both.
0
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Perched on a dramatic rocky bluff, just steps to the shore. Three bedrooms, queen, twin, queen, 3/4 bath and half, laundry, kitchen and breakfast nook, living room with woodstove, large enclosed porch. Mooring available. Also, a knotty pine couples cabin with bath and kitchenette.
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East Bay Two Bedroom.
~ Beds
~ Baths
House
0
$1,200 /week
0
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Quiet wooded perch overlooking the water, this log home offers wide covered screened porch, living room, kitchen, bath, and sunny deck overlooking East Penobscot Bay on the horizon.
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Bonnet Farm
7 Beds
4 Baths
House
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$13,000 /week
0
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Prominent Boston attorney, Charles Sumner Pierce built his Shingle Style cottage with Colonial and Greek Revival influences in 1902 as a year-round farm sited on a rise amid open fields meeting the ocean. Bonnet Farm, centrally located in midcoast Maine on the island of Islesboro, has been a summer vacation destination still owned by his grand and great-grand children.
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