1 - Dark Harbor Five Bedroom Home
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. Available June 24th to July 24th.
2 - The Red House
Delightful, well sited and cared for Dark Harbor vacation cottage. Four bedrooms, 3.5 baths. Master with king has bath downstairs and 3 bedrooms, two with two twins upstairs sharing a bath and another with one twin and private bath. Master and shared bath have shower/tubs. Two working fireplaces; sitting room and grand room. Plenty of wood. The house comes with the use of the dock. Wifi, two TVs in kitchen and grand room. Large deck with water view. Prefer no dogs.
$5,500 per week, two-week minimum.
3 - 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.
$3,000 a week.
4 - 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.
$5,500 a week, two week minimum.
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.
$1,000 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.
$2,750 a week. Attractive discounts for multiple week bookings.
12 - Spectacular Sunset Views of the Bay and Hills. Delightful Ferry Road tuck away four-bedroom shingle cottage just steps to the beach.
Beautifully appointed, open concept living dining and full kitchen. Full length deck facing water side. Master bedroom with king size bed and private bathroom with shower. Flatscreen and recliner. 2nd floor has two large bedrooms (queen, twins) sharing a full bathroom with tub and shower. One large bedroom with King size bed in ground level-daylight basement with wall to wall carpet, 60" flatscreen, lounge area, bathroom and bathroom-laundry room with a shower. Full length deck facing water side. This is one of our nicest homes and just became available again this season.
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 - Pripet Woods Lane
Situated on eight acres on the northeast side of Islesboro, this lovingly restored cottage is a perfect island getaway for a small family or couple. The two-bedroom, two-bath home has a private beach with one of the island’s best views of Penobscot Bay, looking due east across two miles of open water to Castine. The family’s restoration of the 1950’s “Maine camp” has retained the rustic charm of the original structure while updating and appointing it with modern appliances and fixtures to make it a place you’ll never want to leave.
The cottage has a central living space that includes living room, dining area, kitchen, and wood stove. There is a separate entry foyer, which connects to another living room with a television. There is an outdoor porch on the bay side of the house. The main bathroom has a shower and tub, and a second bath, adjacent to the master bedroom, has a shower. The kitchen is well-supplied, as the owners love to cook. An enclosed herb garden is adjacent to the house. Both bedrooms are cozy, include dressers and nightstands, and look out on the bay. The master has a queen bed and the other room has two twin beds. A washer/dryer is off the foyer. The house is equipped with high-speed wi-fi.
Pripet Woods Lane is a private road with very little traffic. The beach is perfect for strolling, beach-combing, picnicking, wading, and kayaking (there are two Perception kayaks and paddles for tenants’ use). A stone patio and fire pit on the bluff overlook the bay.
Please note that the owners are renting only the waterfront side of the house, which includes everything described above. The other half of the house will be closed off and vacant during rental periods. The cottage is a smoke-free home, and no pets. Two-week and one-month rentals are preferred, however, the owners will consider one-week rentals in the month of June.
$1,800 a week in July.
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.
$2,000 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.
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.
27 - Billy Shore Drive Todd Cottage
Secluded down a dead-end dirt road, this beach-side cottage sits in the lap of a beautiful sand and pebble beach, so close you can flip a coin into the water from the screen porch at high tide. The building was a Sears and Roebuck kit house of 1923 which was recently remodeled with a new bath and a half, kitchen and master bedroom. The owners have retained the original charm, removed the funk, and added more comfort and convenience: outside shower, inside bathtub, a wood stove for chilly nights. Three bedrooms include a king-size bed, a double and a pair of twin beds. Above the screen porch is a sleeping loft with another single bed. A stand alone bunkhouse has large bunk beds for a total of beds for ten! Bring your extended family and let the kids find green crabs among the rocks while you watch the osprey’s hunt as you have cocktails on the deck.
$2,100/week or $8,000/month, July or September.
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.
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.
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 for cottage
Also, a knotty pine couples cabin with bath and kitchenette
$400 a week for cabin or $1,100 for both.
38 - Robbins 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
You'll be Lord of the Isles on your own Maine bluff. This sunny A-Frame overlooks Penobscot Bay, has 2 private beaches, 6 acres of woods and shore, and utter privacy; a total escape from the 21st century on a beautiful and non-commercial island.
Sunbathe on a wide deck overhanging a blue slate cliff, with one of the best ocean view in Maine! Oakhead is a regular nesting ground for osprey and bald eagles.
It's in the middle of wonderful sailing waters with deep water anchorage off of the rocky beach and mussels. There is also good swimming nearby at Big Tree Beach.
A perfect place for kayaking, beach combing, picnicking, biking and hiking. Franklin Stove for cool nights, hammock for hot days. Cabin sleeps 5 comfortably, master bedroom double-bed, a small single bedroom, and a sleeping loft for 2-3. Includes a modern, fully equipped kitchen, new bathroom with tub/shower and laundry with washer-dryer. The dining area has a beautiful view overlooking the water and deck.There is WiFi and a TV with limited local reception (DVD player for movies).
$1,680 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, bath and a half. 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.
$850 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. Phone, directTV, and washing machine.
$1200 a month, two to three months $1100 a month, four to six months $1000 a month.
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.
$900 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.
$850 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, large deck, washer-dryer. Minutes to wonderful coves and beaches. No smokers, no pets.
JUNE 17 - JULY 1: $ 900.00 PER WEEK
JULY 1 – SEPTEMBER 2: $1,000.00 PER WEEK
SEPTEMBER 2 - SEPTEMBER 16: $ 900.00 PER WEEK
Price includes cleaning and trash removal costs.
DISCOUNTS AVAILABLE FOR MULTI-WEEK RENTALS!
$ 50.00 off for 2 week rental
$ 100.00 off for 3 week rental
10% off for 4 week rental
$200.00 security deposit plus 9% sales tax. Fee includes cleaning and trash removal costs.
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.
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