Dingley Winter Retreat Tranquility Redefined. The Maine House on Dingley
Photo Gallery
Billiards / Exercise Room
Dining Room
Exterior
First Floor Half bath
Hot Tub
Kitchen
Living Room
Maine House Common Areas
Primary Suite
1 King Bed
Primary Suite Bath
Private Office
Second Floor Half Bath
Second Floor King #1
1 King Bed
Second Floor King #2
1 King Bed
Second Floor Twin
2 Twin Beds
Sunroom #1
Sunroom #2
Views around the Property
Rate –
$750-850/nightSize –
4 Bedrooms • 4 Bathrooms (2 full, 2 half) 4 Baths (2 full, 2 half) • Sleeps 7-10The Maine House – Your Winter Sanctuary
Drive across the bridge onto Dingley Island and step into the Maine House, the heart of our 38-acre oceanfront retreat. In the winter months, the home wraps you in warmth and comfort, offering water views from nearly every room that make each moment feel serene and extraordinary.
Curl up with a book by the wood-burning stone fireplace in one sunroom, which features vaulted ceilings and a large sectional couch, or enjoy the other sunroom, offering stunning views of the sunrise, a serene spot to start the day. Gather for games and fitness in the Billiards room, which includes a pool table, treadmill, and Peloton bike. The living room, with ample seating, a gas fireplace, and a Steinway piano, is perfect for relaxing, playing music, or enjoying panoramic water views. The private office provides a quiet space to work, read, or plan your day. The kitchen, with high-end appliances, ample storage, and stunning water views, is perfect for preparing hearty meals, while the dining room invites long, cozy dinners. Quiet nooks throughout the house offer spots to sip hot cocoa or simply soak in the beauty of the season.
Every corner of the Maine House reflects the essence of Maine: natural materials, soft coastal colors, and thoughtful touches for comfort. The Billiards room doubles as an overflow sleeping area with two twin beds, making the home ideal for families or multi-generational groups.
Guests are welcome to explore the Bunkhouse and Treehouse, which are part of the island experience. Please note these structures are seasonal and not heated, and water is turned off in the Bunkhouse during winter months.
Key Features & Amenities
Sleeps 10 guests: 4 bedrooms + overflow in the Billiards room with 2 twin beds
Primary suite: water views, private bath with whirlpool tub and walk-in shower
Three additional bedrooms: two with king beds, one with two twin beds, water views from nearly every room
Two sunrooms:
Sunroom with wood-burning stone fireplace, vaulted ceilings, and a large sectional couch
Sunroom with stunning sunrise views, perfect for morning coffee or quiet reflection
Living room: ample seating, gas fireplace, Steinway piano, panoramic water views
Billiards room: pool table, treadmill, Peloton bike, play space, overflow sleeping
Private office: quiet workspace
Kitchen: high-end appliances, ample storage, and stunning water views
Dining room: spacious, inviting, perfect for long meals
Bathrooms: soft towels, high-quality toiletries, thoughtful finishes
Outdoor spaces: decks and patios with stunning water views
Hot tub: usable in colder months for a cozy, steamy retreat
High-speed fiber internet
Seasonal access to Bunkhouse and Treehouse
The Maine House is more than a vacation rental. It’s a winter sanctuary, a place to relax, enjoy the water views, and recharge by firelight. Cozy up, watch the changing skies, play, work, or simply unwind, and make memories that last a lifetime.
Availability
About the Owner
Hello, I'm Mark. I’ve been maintaining and managing this estate for the owners for over 20 years, and we truly enjoy hosting guests and sharing the experience of island life here. We know the property and the area inside and out and are always happy to share local recommendations or answer questions, while still respecting guests’ privacy. Our goal is to make your stay easy, comfortable, and memorable. We’re happy to welcome guests and share a special place on Dingley Island. The owner and I have worked together putting great care into creating a space that’s welcoming, clean, and thoughtfully set up so you can settle in and enjoy your stay right away.
Location
Harpswell, Maine
Amenities
| Property Type | House |
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| Accommodation | Entire Home |
| Check-In | Lockbox |
| House Rules |
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| Setting & View |
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| General |
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| Kitchen |
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| Bathrooms |
4 Bathrooms (2 full, 2 half)
4 Baths (2 full, 2 half)
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| Sleeping Arrangements |
4 Bedrooms,
sleeps 7-10
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| Entertainment |
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| Family |
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| Outdoor |
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| Pool/Spa |
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| Vehicles |
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| Theme |
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| Attractions |
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| Leisure |
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| Sports & Adventure |
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| Safety |
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| Expectations |
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| Check Out Tasks |
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| Accessibility |
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Rates
| Season | Night | Weekend Night | Weekly | Rate |
|---|---|---|---|---|
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Unavailable Apr 29–Oct 31. See summer listing or contact us 4/29 - 10/31 |
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Sleeps 10 - Off peak Nov 1- April 28 11/1 - 4/28 |
$715 | $850 | $5,275 |
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Cancellation Policy: One hundred percent (100.00%) of the total booking charges (less $500.00 taxable cancellation fee) will be refunded if the cancellation is made more than 60 days prior to the arrival date of the reservation. For cancellations made within 60 days prior to the arrival date, no refund will be issued. Grace period with free cancellation for 48 hours after booking if arrival is at least 48 hours away at time of booking.