Islesboro Vacation Rentals - Summer 2011
(Prices subject to change. Availability for any rental to be verified.)
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.
2 - Ames Cove
Turn-of-the-century Dark Harbor shingle-style cottage on 16 acres of fields and ponds with 1,275 feet of waterfront. Seven bedrooms, six fireplaces, five baths.
$6,800 a week in August. Two week minimum.
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.
$5,500 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.
4 - Seal Harbor Big Tree Beach Post & Beam
Wonderful sunset views over the bay and hills from this substantial 2,500 square foot, four-bedroom home tucked amid the evergreens on five acres with 258 feet of beach front and dock. Delightuful landscaping, private and protected with room for a guest house. Barn guest apartment and heated garage/shop. Just about all the amenities you'd need to enjoy a coastal Maine island community.
$7,500 a week in July.
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.
$4,500 a week. Two week minimum.
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.
$3,000 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 - Fishhawk Over Big Tree Beach
Waterviews from every room on this peninsular location. Space and elegance. Master bedroom with fireplace, two guest bedrooms, two baths. No pets.
$2,400 a week. Two week minimum.
11A - Newly Listed for 2012! Edward Adams Cottage
Grand nine-bedroom Dark Harbor Tudor/Colonial Revival summer home. Six fireplaces, five baths, sleeps twelve. Music room, dining room, eat-in kitchen with new appliances, sunporches, covered back porch, second floor balcony. Meticulously landscaped, winding pathway of granite steps, stone terrace. Walking path to water and picnic area with fire-pit across East Shore Drive. Satelitte TV, wi-fi internet.
$4,500 a week.
12 - Classic Saltwater Farm & Dock
Charming 6-BR rambling farmhouse, meadow & orchard, dock, west view, beach.
$4,000 a week.
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.
14A - Sprague's Cove Log Home
3-BR, sleeps 8, large stone hearth, deck. Private, quiet, deepwater, 10 acre woods.
$1,700 a week.
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 - Dark Harbor Compound
Picturesque winding drive to west shore bedroom and loft cabin right on the water. Completely renovated to highest expectation. No pets. Read More
$5,000 a month, $2,000 a week
1 Bedroom boathouse
$4,000 a month, $1,250 a week.
17 - Avalon
Idyllic and private setting on almost 10 acres on Turtle Head. Professionally landscaped, easy beach access, cutting flower garden, natural fern beds and boardwalk accented with rock walls. Full kitchen w/ granite counter tops, gas stove, full bath with jacuzzi, laundry. Living room woodstove, pull-out couch. Master bedroom with vaulted ceiling and loft with double and single beds. Screened porch dining. Shoreside sitting deck for exquisite sunrises and sunsets. Turtle Head nature trail nearby. No pets.
$2,000 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.
$2,200 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.
23 - Hewe's Point Cape
3 bedrooms, 2 full baths, living room with fireplace, dining room, attached 2-car garage on 2 acres of lawn and birch trees right on Broad Cove.
$1,800 a week in July.
24 - South Shore Two Bedroom Cottage & Beach House
Kitchen-dining-living room, shower, washer-dryer. Covered porch. East Bay waterviews over meadow, beach house right on the water with two bedrooms (no utilities).
$1,200 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
Oceanfront three-bedroom cottage with panoramic sunrise views of Penobscot Bay, easy beach access and deep water.
$1,600 a week.
27 - Pripet Woods Lane Two Bedroom
Private getaway at the water's edge, charmingly renovated, new kitchen and living room. Easy access to beach and boating, exceptional easterly waterviews towards Castine.
$1850 a week.
28 - Ryder Cove Shingled Cottage
Wonderful ocean view, right on the beach, three double bedrooms, knotty pine interior, full and half baths, library, game room, cozy fireplace with stove in the living room. Kitchen and deck. Pets case by case. No smoking.
$1600 a week.
29 - Ferry Road Cedar Shingle Three Bedroom
Right on the shore. Knotty pine interior, neat as a pin. Full bath, washer-dryer, full kitchen, living room, family room. Wonderful water views and beach.
$1,400 a week.
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.
31 - Ryder Cove Quaint Three Bedroom Cottage
Right on the shore, steps to beach.
$1200 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.
$1,200 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.
$1,100 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 - Dockside
Boater's dream, 2-BR, sleeping loft, right on rocky western shore, great deck, views. No pets.
$1,100 a week.
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.
$1,300 a week in August.
39 - Oakhead A-Frame at the Narrows
Perched on a 5-acre shore bluff and beach with a spectacular views of East Penobscot Bay. Master bedroom with double, sleeping loft with twins, kitchen, dining area, bathroom with washer-dryer, Franklin stove/fireplace, and spacious deck.
$1,300 a week in August & September.
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 - Broad Cove A-Frame
Water's edge, exceptional views, 2 BR, bath, kitchen, woodstove, washer-dryer, deck. Even a piano! No pets.
$850 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 - Ryder Cove Rustic Three Bedroom Cottage
Quiet enclave, porch looks over beach/ocean, Sleeps 6.
$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.
$750 a week.
52 - Rambling Four-Bedroom Farm House
A country flair with just a short drive to beach and ocean access. Large kitchen and dining areas, double bed, king size bed, and single beds in the remaining two bedrooms. 2.5 baths with jacuzzi. Laundry facilities. Gas grill. Large covered porch and patio. Great space.
$800 a week.
53 - Abbey at Farrow Farm
Wonderfully unique living and family space. New two bedroom home, cathedral ceiling, third storey turret sitting room, full kitchen, bath, living room, first and second storey decks. Charming landscaping, rock wall, gardens.
$900 a week.
Additional first floor living room with kitchen, sleep sofa.
Both for $1,500 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.
$750 a week. June 9th to June 30th.
$900 a week. June 30th to September 8th.
$750 a week. September 8th to October 20th.
$200 security deposit. Pet rates; $100 plus $200 security per pet. Discounts; 10% month, $200 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.
Commercial Rentals - 2011
(Prices subject to change. Availability for any rental to be verified.)
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
Email: oldhamip@midcoast.com














































































































































































































































