1 - Williamson Cottage
'One of the prettiest cottages in town', Belfast Republican Journal, May 16, 1895. Magnificent Shingle and Colonial Revival style Dark Harbor village home designed by Bar Harbor architect Fred L. Savage. Dramatic setting of open lawn to a rocky shoreline with sweeping East Penobscot Bay and ocean views. The elegant residence offers comfortable living, dining and library rooms with fireplaces, a pantry and kitchen and grand porches on the first floor. The second floor includes six bedrooms, three bathrooms and an office. A guest mooring in Ames Cove of Gilkey Harbor on the western side of the island is available for use by tenant. The cottage underwent a substantial exterior renovation and was completely refurnished in 2009, including new mattresses and new linens throughout.
$7,000 a week in July & August. Monthly rentals preferred.
3 - Elegant Water's Edge
In heart of Dark Harbor on Gilkey's Harbor close by the Yacht Club. 4 bedrooms, 4 fireplaces, 3 - 1/2 baths. Master bedroom fireplace, jacuzzi. 3-bedroom, 2 bath guest wing. Rich hardwood flooring.
$6,800 a week.
3A - 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.
$5,500 a week.
5 - 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.
Breezeway entry/sunroom with wood burning stove and seating group. Great room with wood burning Rumford fireplace and library alcove, seating group includes whicker sofa and four chairs plus benches.dDining room with table seats twelve includes seating for six. Kitchen with large island and seating with state of the art Viking range, SubZero refigerators (2), Miele oven and microwave and dishwasher, fully outfitted pantry with recycling, glassware and service for twelve plus.
Studio with desks, stereo hookups, fax machine. Hall bath with shower, laundry room. Covered porch adjacent to kitchen and studio and entry. Two full baths, one with shower, one with whirlpool tub. Outdoor equipment includes porch seating for eight (plus and outdoor dining table), lounge seating for six, and a hammock, plus charcoal grill. Hardwood or tile floor throughout, internet access with wireless capability, hard wired and wireless phone and alarm system.
$5,000 a week in June & September.
$6,000 a week in July.
$7,000 a week in August.
6 - Billy Shore Drive, Ryder's Cove
Spectacular views from this renovated rambling shingled cottage. Five and a half bedrooms, three bathrooms, enclosed porch and large deck, dock and mooring.
$3,500 a week.
Separate guest cabin sleeps four, double down, loft twins, kitchen, 3/4 bath, living/dining room.
$1,250 a week.
7 - 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 panelling.
$3000 a week.
8 - Exceptional West Bay Home
Picture post card views from most every room of West Penobscot Bay and Islands over 4 acres of lovely fields, pond, and beach. 4 bedrooms, 2 full baths, large living room, dining room, sunny kitchen, plus sunroom and deck. Mid island location.
$2,750 a week. Two week minimum.
9 - Cedarpoint
Dramatic oceanpoint, exquisite cottage, golden sunsets over Camden Hills, 3 bedrooms, 2 full baths, large living room with fireplace, spiral stairway, private beaches, dock. No pets.
$3,000 a week.
10 - Grand Farmhouse
Wonderful east bay views over meadows and woods, delightful paths, beach. 4 bedrooms, 3 baths, kitchen, breakfast nook with fireplace woodstove, dining room, living room, study, deck, finished attic, bath.
$2,500 a week.
11 - 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.
Fish Hawk is located just north of the "narrows" that separate Dark harbor from Pripet on Seal Harbor on the west Penobscot Bay with a 2 ton permanent granite mooring capable of taking boats up to a 48' in length. The mooring may be available under separate arrangements made in advance.
The house itself is situated on 5+ private acres and was designed and built to take maximum advantage of its site and the 270 degree waterfront exposure. The bathrooms are the only rooms that do not have direct water views. There are 3 bedrooms capable of accommodating up to 8 people if the futon in the walk-out TV room is used downstairs. Window seats are wonderful napping locations in front of the windows on the second floor. There are two fireplaces, one in the "den" at the living level, another in the master bedroom. The master bedroom has its own private bath. A powder room is located on the second floor and full bath (with shower) at the living level. The kitchen is fully equipped with late model appliances and a washer/dryer just opposite the kitchen. Decks surround the house, the favorite of course, the "den deck" overlooking the Bay and the Camden Hills.
$2,750 a week. Attractive discounts for multiple week bookings.
13 - Stately West Bay Summer Cottage
Grand ocean view overlooking past lovely formal gardens and lush meadow to the beach. Sunporch, kitchen with pro gas range, dishwasher, formal cathedral ceiling living room with fireplace, entertainment room with woodstove, brick paved sunroom, two baths, laundry. Lots of pine and tile flooring. Master bedroom queen, blue bedroom twins, yellow bedroom queen.
$2,400 a week. July through mid August.
14 - Sabbathday Harbor Look Out
Sweeping views of Ryder Cove, Islesboro's eastern shoreline. Private wooded location, well-maintained, 3-BR home sleeps 8. King & twin, queen & twin, 2 doubles, bath and half. AC, satellite dish, 2 large screen tv's, WD, dishwasher. Great porch. Path to shore. No smoking.
$3,400 a week / $2,200 June & September.
15 - Broad Cove Saltwater Farm
Simply one of the best views on Islesboro over the cove and Gilkey Harbor. Renovated island farmhouse. Three bedrooms, three full baths, jacuzzi. Living room fireplace and bay to deck. Vegetable garden, large field, not far from ferry and town dock.
$2,300 a week in June & July.
16 - Cove Side
Picturesque winding drive to west shore bedroom and loft cabin right on the water. Completely renovated to highest expectation. No pets. Read More
$3,000 for 1 week, $4,000 for 2 weeks, or $6,000 for 3 weeks.
17A - Heavenly Daze at Turtle Head
Well-crafted, fully furnished and handicap accessible home perched on rugged ledges in an enchanting and private woodland setting. Completely renovated. Glorious sunsets, simple and inviting gardens, footpaths. Just steps to a picturesque typical Maine beach. Main house has spacious master suite including walk in shower with heated tile floors. This house has one floor with fully stocked kitchen, family room with floor to ceiling windows looking out on Penobscot Bay, vaulted ceilings, exposed natural wood beams, a centrally located wood stove fireplace perfect for a cold fall evening. Having friends join you for a few days... the fully furnished one bedroom apartment above the detached garage has a kitchenette, full bathroom, living area and queen size bed is perfect for guests. Charcoal grill for slow and relaxing dinners and an ocean side landscaped fire pit perfect for s'mores while you watch the stars. No pets or smoking please.
$1,800 a week.
18 - Bayview Farm
Rambling Maine farmhouse with five bedrooms, three baths, upscale kitchen and woodstove, dining room, living room, parlor, great family room. Sleeps nine with two double beds, queen, twins, and single. Sweeping views of bay from an elevated island vantage point amidst fields. Large barn for family activities and vegetable garden.
$1,800 a week.
19 - Marshall Cove Post & Beam
Exceptional waterfront three-bedroom home in a private open meadow. Spacious and crisp interior, hardwood maple flooring, . Large kitchen with gas stove, dishwasher, living room hearth and woodstove. Master bedroom (queen), bath/shower, half bath, 2 second floor guest bedrooms (twins, queen) and full bath, washer-dryer. Covered and screened porches to enjoy this idyllic setting. Lovely landscaping. Easy beach access.
$2,000 a week in July.
20 - Scull Cottage
Turn of the century Dark Harbor cottage, completely refurbished to highest expectation; formal living room with fireplace, dining room with fireplace, kitchen, pantry, laundry. Seven bedrooms; master bedroom with fireplace and view to west bay, twin bedroom with fireplace, double bedroom, twin bedroom, nursery, double bedroom, 3/4 bedroom, 4 full baths, plus staff rooms, glassed porch, and elegant grounds.
$2,000 a week in September.
21 - East Narrows
Waterfront three bedroom cedar-shingled cape, great views, beach, kitchen, DR, LR, fireplace, two full baths.
$1,500 a week.
21A - Cair Paravel "Castle"
On Islesboro's western shores. Three bedrooms, three stories, two full baths, almost magically tucked on a private site amidst wonderfully landscaped gardens and enchanting ocean views. Come get away.
$1,600 a week.
22 - Hewe's Point Cottage
"Come enjoy 'life in the slow lane' at our little piece of paradise." This truly charming cottage has a spectacular water view, 100 feet to the shore, glass/screened porch, two bedrooms, one bath, fully equipped kitchen (no dishwasher), linens, phone, a/c, heat, satellite tv, dvd player and washer/dryer. Great owners who will welcome you with warm island hospitality. If you want to get away and just let the world go by, then this is the place for you!"
$1,500 a week.
22A - Barnegat, Elegant Post & Beam
Just south of Dark Harbor with all the comforts, convenience, and privacy you'd expect of a well-appointed summer cottage and just a stroll to the town beach. Three luxurious bedrooms, two full baths, vaulted ceilings. Top of the line kitchen, cozy sitting room & wood stove, living room and fireplace, formal dining room, office, laundry, outside shower. Patio with wicker and dining with 12 foot table with umbrellas, meticulous grounds and abundant flower beds. Dog friendly with owner permission.
$1,600 a week from June 15th to July 8th, September, & last 2 weeks in August.
23 - Seaside; Ryder Cove Lane Cottage & Dock.
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.
$2,400 a week.
23A - Ryder Cove Guest House
Just across the lane from #23 with two bedrooms, two baths, loft bedroom, kitchen, vaulted living/dining room, covered porch. Well appointed, great space. Located in quiet summer enclave.
$1,200 a week.
24 - South Shore Two Bedroom Cottage
Kitchen-dining-living room, shower, washer-dryer. Covered porch. East Bay waterviews over meadow, path to pristine beach.
$900 a week.
25 - Crow Cove
Private, 4-BR house, 2.6 baths, private beach, deep water mooring. Large living room, elegant cathedral ceiling dining room. Large deck, stairs to beach.
$2,000 a week.
26 - Doc's Harbor
Prime Oceanfront 3-Bedroom Cottage. Panoramic sunrise views of Penobscot Bay, easy beach access and deep water.
29 - Rambling Farmhouse in North Islesboro
Bring the whole family! This elegant and delightful island home has five bedrooms and sleeps ten people. Room configurations are as follows. Upstairs: Master bedroom king, guest room twins, guest room single. Rustic bunk room with four singles and full bath room. Downstairs: single bedroom and full bath. Kitchen, living room, dining room, library, great rustic tv room. Ten is max but eight is a better fit. Early July, late August. Exceptions considered for monthly stays.
30 - Hewe's Point Broad Cove
Waterfront three bedroom, fully equipped cottage, wonderful deck, view! 2005 second storey addition includes 2 full baths, laundry. Lawn slopes gently to private beach. Walk to public playground, tennis courts. Near village, shops, boating, library, Historical Society. Sleeps four or family of five with small children.
$1,900 a week.
32 - East Bay South Shore Three Bedroom
Well-kept Maine farmhouse with sweeping east bay views and path to beach. King, queen, twins, sleep sofa in study, bath and half, laundry. Walk to Big Tree Boating and beach, general store. Bike to town tennis, library, historical society. No smoking or pets.
$800 a week.
33 - Hewe's Point Road Waterfront Home
Tucked away off a cherished dead-end road, this well built and maintained three bedroom home offers views and access to Islesboro Harbor, a tidal east bay cove. Full bath, washer-dryer, large open deck, outside shower. Stroll to the library or historical society. Digital TV and wireless Internet, half bath upstairs.
$1,200 a week.
34 - Hewes Point Couple Cottage
Wonderful view and beach access. Queen-sized bedroom, shower, kitchen, living room with queen sleep sofa, screened porch.
$800 a week in June & July.
35 - Charming Three-Bedroom Island Home
Located north of the Narrows in a pleasant rural area of Islesboro. Picture yourself rocking on the covered porch beneath large shade trees. Kitchen, bath, laundry, dining room and living room. Comfortable high ceilings. Three bedrooms upstairs; queen, double, and twins. Large sunny lawn area for croquet. Beaches are a short drive and the general store is just a stroll.
36 - 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.
$900 a week.
Also, a knotty pine couples cabin with bath and kitchenette
$300 a week or $1,000 for both.
37 - Driftwood at Ryder Cove
Next door to Robbin's Nest. Rustic three bedroom cottage on the beach. Washer.
$1,400 a week
38 - Robin's Nest
Two bedroom cottage right on Islesboro's nicest beach. Full kitchen, woodstove hearth, knotty pine interior, screened porch, and the best ocean views.
$1,400 a week in August.
39 - Oakhead at the Narrows
Oak Head is an enlarged A-frame situated on a shore bluff with a spectacular view of the Penobscot Bay and surrounding islands. This completely private, wooded 6 acre peninsula is a total escape from the 21st century on a beautiful and non-commercial island. It is in the middle of wonderful sailing waters and has deep water anchorage off of the rocky beach with mussels and beach combing. There is good swimming nearby at Big Tree Beach.
This fully furnished A-frame has a master bedroom with a double bed and wonderful water view through the trees, a sleeping loft upstairs with 2 twin beds and an extra bed, if needed, a small study on the first level with a single bed/couch. There is a generous deck across the whole front of the house. Inside, there is a Franklin stove/fireplace, bathroom with washer/dryer and bathtub/shower, and kitchen with all new appliances. The dining area has a beautiful view overlooking the water and deck. $1300 weekly, two week rentals preferred.
$1,300 a week. Two week rentals preferred.
40 - Circa 1848 Four Bedroom Home
On the quiet end of town, set back from the main road on 20 acres, near Church Turn. Recently thoroughly renovated. Kitchen with woodstove hearth, dining room, living room, two full baths. Washer-dryer, dishwasher. Large, sunny yard, not far from beaches and boating.
$1,000 a week.
41 - Gooseberry Sunsets
Light airy 2 Bedroom home sleeps 4, right on the shore, very nice, all conveniences.
$1,250 a week.
42 - Ryder Cove Boathouse
Delightful couples cottage with exceptional view of East Bay and access to Ryder Cove for water and beach activities.
$1,000 a week in July.
43 - East Bay Two Bedroom
Quiet wooded perch overlooking the water, this log home offers wide covered porch, living room, kitchen, bath, freshlypainted, new furnishings.
$800 a week.
44 - West Bay Three Bedroom
Private beach, 16 acres, fully equipped home, master bedroom, spiral stairs to 2 bedrooms, nicely appointed, sunspace, pine floors, 2 baths, washer-dryer. No pets.
$850 a week.
45 - Broad Cove Getaway
Perched above the cove with sweeping water views! Sleeps four, three single beds and futon.
$1,000 a week.
46 - Valdermar Two-Bedroom Cottage
Sited on a hillside just above the owner's sister's house with views and beach front access to West Penobscot Bay. Two bedrooms; double and twins, living room with water view, kitchen, full bath.
$800 a week.
47 - Woody Point Ryder Cove Two Bedroom
Comfortable summer cottage, great porch and view.
$800 a week in June & July.
48 - Gilkey Harbor Couple's Cottage
A charming stone's throw from the water's edge, convenient to ferry.
$800 a week.
49 - The Gables, Hewes Point
This three bedroom cottage near end of Hewes Point Road is back on the rental market after extensive perking up. Fresh kitchen and bath, living room and dining room. Upstairs bedrooms sleep five; double, twins, single. Darling covered front porches, shoreside rear porch water view. Beach access across the lane and large yard for lawn sports.
50 - Rebel Hill Two-Bedroom Log Home Hideaway
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. Eat-in kitchen, gas range, cherry cabinets, microwave. Great covered porch, picnic table area with fire pit and swing with just a distant smidgeon peek of the East Bay.
$800 a week.
51 - Attractive Waterview Studio Apartment
Fully furnished one bedroom apartment sleeps six. Full bath, sleeping loft, sleep sofa, day bed. Located approximately 3 miles from village (Church, post office, grocery store, garage, health center etc.) Excellent public swimming beach is just a short walk down the hill.
$500 a week.
54 - Crow's Nest Cottage
Delightful two bedroom home located "up-island" on the quiet end of Islesboro. Looking across to 10 acre fresh water Meadow Pond, a neat wildlife refuge. The cottage is a 100 year old, small, shingle sided, cape which has been completely renovated in charge deck, washer-dryer. Minutes to wonderful coves and beaches.
$800 a week. June 21st to June 27th.
$1000 a week. June 27th to September 5th.
$800 a week. September 5th to October 4th.
$200 security deposit. Pet rates; $100 plus $200 security per pet. Discounts: 10% month, $ 100 off 3 weeks, $50 off 2 weeks.
55 - Dark Harbor Colony Road Four-Bedroom
Living room, kitchen, dining room, family room & laundry. 2 and half baths, covered porch. Pleasant family neighborhood, walk to shops and Dark Harbor pool.
$850 a week.
56 - Tehan Lane New Four-Bedroom Cedar Shingled Home
Located on quiet side lane. Spacious dining-living room. First floor bedroom and bath. Large sunny yard and woods. Quick drive to ferry and town dock for boating.
$1,000 a week.
57 - Marshall Cove Road Cabin
Nestled in the Woods. Just refurbished three bedrooms (twins, queen, full), two baths, kitchen, dining room, living room. Access to private shared sandy beach. No smoking.
$1,000 a week.
58 - Chestnut Hill Three-Bedroom, Two Bath
Glimpses of the water and just a walk to water access, tennis courts, the library, historical society. Short drive to markets and boating school. Pleasant homey summer space under the shade of the chestnut trees.
$700 a week.
Historic In-Village Commercial Gallery
Approximately 1,000 square feet of retail space on the corner of Dark Harbor village amid shops, restaurants and real estate offices. 10 foot stamped tin ceilings. High visibility, excellent summer traffic.
Dark Harbor Village Restaurant
Elegant dining opportunity in the heart of island summer activity with well-established clientele. Approximately 3,000 square feet and three dining rooms in two storeys, ample parking. Major renovations in 2000, this well-equipped restaurant offers flexible dining, service, prep and storage facilities to meet your innovation. Owner willing to work with a partner to reopen. Will need work. Inquire for more details.
Please inquire about other rental situations not appearing on this list.
John Oldham, Broker
P.O. Box 300
Islesboro, Maine 04848
Office: (207) 734-8809
Summer: (207) 734-6901
Fax: (207) 734-6863