Vacation

Rentals

Vacation to the stunning
island of Islesboro.

3 Baths

5 Beds

Henry Hatch House

Henry Hatch House

Near Dark Harbor Village. Wonderfully appointed five bedroom historic home, queen downstairs, three bedrooms upstairs with double beds each and one bedroom two singles. Two full baths with shower and separate tub each, and two half baths.
$10,000 /month

1.5 Baths

2 Beds

Meadow Pond 1850's Greek Revival

Meadow Pond 1850's Greek Revival

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.
$1,500 /week

House

1 Bath

2 Beds

Rebel Hill Log Home

Rebel Hill Log Home

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.
$1,000 /week

House

~ Baths

2 Beds

Woody Point, Ryder Cove Lane

Woody Point, Ryder Cove Lane

Comfortable summer period harking back to the Ryder Cove heyday of the 1800’s cottage, great porch and view.
$1,000 /week

Home

2 Baths

3 Beds

West Bay Three Bedroom.

West Bay Three Bedroom.

Private beach, 16 acres, fully equipped home, master bedroom, spiral stairs to 2 bedrooms, nicely appointed, sunspace, pine floors, 2 full baths, washer-dryer. No pets.
$1,000 /week

House

~ Baths

~ Beds

East Bay Two Bedroom.

East Bay Two Bedroom.

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.
$1,000 /week

House

4.5 Bath

3 Beds

Ryder Cove Cottage.

Ryder Cove Cottage.

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.
$1,500 week/cottage or $600/cabin or $1,800 both.

Cottage / Cabin

1 Bath

2 Beds

Hewes Point Couple’s Cottage

Hewes Point Couple’s Cottage

Wonderful view and beach access. Queen-sized bedroom, shower, kitchen, living room with queen sleep sofa, screened porch. Enjoy strolling and the quiet pace of an historic island summer enclave with no through traffic.
$1,000 /week

House

2 Baths

2 Beds

Green Cot, Ryder Cove Guest House

Green Cot, Ryder Cove Guest House

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.
$1,500 /week

House

2 Baths

3 Beds

Seaside Cottage

Seaside Cottage

Lovely home in treasured 19th century Islesboro summer enclave. Three bedrooms; queen, double, twins, two baths, large kitchen, dining, and living room. Spectacular views of East Penobscot Bay with dock and float. $3,000 weekly
$3,000 /week

House

2 Beds

3 Beds

East Narrows Oceanfront

East Narrows Oceanfront

East Narrows Oceanfront sunrise cedar-shingle cape at the Narrows! Exceptional East Penobscot Bay Views. Three bedrooms, two full baths, first floor master suite, very functional galley kitchen overlooking water, first floor laundry, cozy living room, dining room opening to shoreside deck and fire pit. Spread out in two large bedrooms upstairs with full bath.
$2,000 /week

House

2 Baths

4 Beds

Parker Cove Lookout

Parker Cove Lookout

Parker Cove Lookout is on the crest of a hill with panoramic views of East Penobscot Bay. It has four bedrooms, two full baths all on about 20 acres with a path to shore and Parker Cove beach where you can hike along to Hutchins Island preserve. Adjacent to Blueberry Hill Preserve, just south of Point Comfort and Pripet Riding Program.
$2,500 /week.

House

2.5 Baths

3 Beds

Marshall Cove Post & Beam

Marshall Cove Post & Beam

$3,000 a week

House

2 Baths

3 Beds

Fish Hawk

Fish Hawk

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.
$3,000 /week

House

4 Baths

7 Beds

Bonnet Farm

Bonnet Farm

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.
$10,000 /week

House

5 Beds

Classic Ryder Cove Cottage

Classic Ryder Cove Cottage

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.
$3500 /week

House

3 Baths

4 Beds

Miramare Shingle

Miramare Shingle

Miramare Shingle style state of the art home of 4500 sf with four bedrooms, two with queen beds, one with king bed (or two twins), one with two twins (or king bed), three full baths, great room, dining and gourmet kitchen, first floor sunroom, studio and second floor lounge. Over 250 feet of bold ocean waterfront with beach areas. Gorgeous sunset views over Camden Hills.
$5,000+ /week

House

4.5 Baths

7 Beds

Dark Harbor Cottage

Dark Harbor Cottage

Overlooking fabled Dark Harbor Pool to East Penobscot Bay and Camden Hills on West Penobscot Bay, this seven-bedroom home is situated just a stroll from the village shops. Enjoy sunrise and sunset water views from relaxing porches. Four and a half baths, meadow to shore. Internet, all linens and kitchenware provided. A wonderful family home for a memorable stay on a quiet island with some of the best sailing waters.
$5,800 /week

House

3.5 Baths

6 Beds

Long Ledge

Long Ledge

Delightful six bedroom Dark Harbor cottage with living room and master bedroom fireplaces, three and a half baths, DirectTV. Access to family compound dock, tennis court.
$3,500 /week

House

3.5 Baths

4 Beds

The Red House

The Red House

Delightful, well sited and cared for Dark Harbor vacation cottage. Four bedrooms, 3.5 baths. Two working fireplaces; sitting room and grand room. The house comes with the use of the dock. Large deck with water view.
$6,000 /week

House

4 Baths

5 Bed

Dark Harbor 5-BR

Dark Harbor 5-BR

Commanding view of West Penobscot Bay. Fully equipped, four full baths. Heated in-ground pool, covered porch. Open meadow and sunsets over the Camden Hills.
$7000 /week

House