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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Oceanfront Mount Desert Island Retreat

Bedrooms 3
Space 1,500 sq ft
Property type house
Minimum Stay 6 - 7 nights


About the property

3+ Bedroom, 2 Full Bath; Sleeps Up To 8 Adults With Additional Room For Kids

The aim and mission of the Windaway Estate is to celebrate the natural, native landscape of Mount Desert Island, and provide a peaceful, beautiful, and FUN spot for family vacations, romantic getaways, and special retreats. The Windaway House, part of the Windaway estate, is a perfect choice for a large family or up to 4 couples who want an oceanfront vacation in Bar Harbor, but prefer to stay just far enough away from the craziness of town. Windaway is the perfect location from which to explore the many beautiful areas of Mount Desert Island. Located at the head of Mount Desert Island in the village of Town Hill (part of Bar Harbor), each town and village of the island is a short drive or ride on the free Island Explorer Shuttle bus (which can pick you up at the end of the driveway!) Acadia National Park takes up the greater portion of the middle of the island, so multiple access points are minutes away. Though the setting is very quiet and peaceful, you'll find all the ammenities you need within a convenient 5 mile radius.

Available by itself or in conjuction with Windaway Loft (vrbo #507900), Windaway House is a new rental offering on MDI, and is a 2 story, 3 bedroom, 2 full bathroom house, with a large great room and beautiful deck. High Speed WiFi internet is included in the rental rate. All beds, bedding, linens and towels are new. One large bedroom has 2 queens, and the other 2 each have 1 king bed. Each floor has a full bath, and there is also a laundry room connected to the first floor bathroom. The large great room has brand new, super comfy seating for lounging or watching TV. There are two deluxe cots in the large closet of the great room, to make the great room an additional sleeping area for kids or more guests. Most appliances and furnishings are brand new, and tastefully coordinated. Kitchenware is high quality (knives are sharp!) and is BPA and Teflon free. Enjoy having morning coffee and breakfast with the sun, and incredible sunsets and star gazing in the evening.

Though there is SO MUCH TO DO on MDI, Windaway is a lovely place to spend a relaxing day. Take a stroll on the shore to look for seashells or sea glass. Even better, bring your kayak (or rent one from National Park Canoe and Kayak Rental- they will deliver and pick up on Saturdays!) and explore the peacefulness of Western Bay from just outside your door. Of particular interest is a small, working Oyster Farm just off the shore, which is owned and operated by the owner of Windaway. At night, take advantage of the ocean side fire pit area and absorb the Maine night sky complimented by the sounds of the ocean. We love and welcome pets but do charge a $75 fee for additional cleaning

More Details

Property Manager
Chelcey Dunham
Member since: 2011
Premier Partner

This VRBO partner has demonstrated and is committed to fast response times, the best rates, and a great guest experience.

Speaks: english
Response time:
Within 12 hours
Response rate:
Calendar last updated:
September 19, 2018

About Chelcey Dunham

Pictured above with his goat friend Marceline at his farm down the road, is Farmer Matt Gerald -the owner of Windaway Estate. Matt lives onsite at Windaway, and is a fixture on the island. Sweet Pea Farm is his day job, and is a working farm, winery, and farm-to-table restaurant just a few miles away. Make it a point to meet him and visit Sweet Pea Farm for popovers, coffee roasted onsite, free wine tastings, brick oven pizzas and Mexican offerings featuring the vegetables grown on the farm.

Chelcey Dunham purchased this house in 1984

Why Chelcey Dunham chose Bar Harbor

After Matt attended College of the Atlantic in Bar Harbor, he decided that he had to remain on MDI. The island holds a very special energy that is both awe inspiring and nurturing. Desiring to be near her son, Matt's mom moved here too, and purchased the Windaway Estate. The property (and Matt!) retain her youthful, vibrant essence.

What makes this house unique

Matt's mom chose Windaway because she fell in love with the spot. Who could resist pristine views, gentle access to the ocean, and the surrounding wooded areas and fields? The buildings have a nostalgic charm and are unpretentious yet tasteful, well designed, and comforting. The experience of BEING on MDI and staying at Windaway is truly a gift to the soul.


Bar Harbor House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 1500 sq ft
House Rules:
  • Max. occupancy: 10
  • pets considered ...
  • children welcome
  • non smoking only
Location Type:
  • Ocean View
  • Oceanfront
  • Away From It All
  • Family
  • Romantic
  • Sports & Activities
  • Tourist Attractions
  • Clothes Dryer
  • Hair Dryer
  • Heating
  • Internet ...
  • Iron & Board
  • Linens Provided
  • Living Room
  • Parking
  • Telephone
  • Towels Provided
  • Washing Machine
  • Wood Stove
  • Coffee Maker ...
  • Dishes & Utensils
  • Dishwasher
  • Kitchen
  • Microwave
  • Oven
  • Refrigerator
  • Stove
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 2 Bathrooms
  • Bathroom 1 - toilet , combination tub/shower , Laundry room and Master bedroom connect to this bathroom
    Bathroom 2 - toilet , combination tub/shower , 2nd floor, in between 2 bedrooms
  • 3 Bedrooms, Sleeps 10
  • Bedroom 2 - 2 queen , Accommodates 2 -4 adults
    Bedroom 3 - 1 king
    Master bedroom - 1 king , First floor; connects to the bathroom. No images yet...
  • Books
  • Satellite / Cable
  • Television ...
  • Deck / Patio
  • Kayak / Canoe ...
  • Lawn / Garden
  • Outdoor Grill
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • marina
  • museums
  • playground
  • restaurants
  • water parks
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • miniature golf
  • scenic drives
  • shopping
  • sight seeing
  • walking
  • whale watching
  • wildlife viewing
Local Services & Businesses:
  • ATM/bank
  • Babysitter
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cycling
  • golf
  • hiking
  • kayaking
  • mountain biking
  • mountain climbing
  • rock climbing
  • swimming
Housekeeping is included in the rental rate, and happens at the end of your stay (not on a daily basis.)


Wonderful! 4.9/5 -
(17 traveler reviews)

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Oceanfront Mount Desert Island Retreat
average rating of 4.882353 based on 17 reviews

Enjoyed our stay

  • 5 of 5

Good experience.

  • Submitted: Aug 4, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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An amazing home away from home

  • 5 of 5

The house was very warm and inviting. It was well stocked with needed items and was the perfect landing spot for our MDI vacation. The beach was an amazing place to watch the sunset and search for shells and the firepit under the stars brought some of our best memories. We are already talking about when we might be able to be back.

  • Submitted: Jul 19, 2018
  • Stayed: July 2018
  • Source: VRBO, from HomeAway
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Great place to stay on MDI!

  • 5 of 5

This was an excellent place for our trip to MDI and Acadia. The accommodations were great. Be mindful that there is no AC but lots of fans and windows to get a good cross breeze. We really enjoyed the fire pit and watching the stars at night. The oyster farmers were kind and were very respectful. Would highly recommend this rental!

  • Submitted: Jul 10, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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This is truly a get away place.

  • 5 of 5

We enjoyed our stay at Windaway very much! Short walk to the beach was great. Secluded enough to be private but close enough to town to do whatever you want. The working oyster farm was interesting to see at low tide. The house was very clean and neat. It was as described with no surprises or disappointments. The house was nicely decorated and is roomy enough to accommodate large families. YES!!, we will return.

  • Submitted: Jun 22, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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Very Clean, Comfortable, Spaciuos Cottage

  • 5 of 5

As an owner of a house cleaning service in a a resort town, I am extremely particular about cleanliness. I have stayed in other places that have not been very clean so I had some reservations. I brought my cleaning supplies in case I needed to clean when we got there. I was pleasantly surprised at how clean the house was. Needless to say, my cleaning bucket just sat in the laundry room for the week. All the linens and towels were clean and of decent quality. I felt comfortable laying my head down every night. There were plenty of supplies on hand to get us started like trash bags, toilet paper, paper towels etc...The kitchen was well stocked with all of the necessities. The house was well decorated without being cluttered. We took the short walk to the water to watch the sunrise and set a few times. There is a nice view outback as well and you can see the water from the windows. We enjoyed being off the beaten path but also being close enough to visit Acadia and Bar Harbor regularly. It's about a 20 min drive or less. Matt, the owner is very friendly and close by in case of any issues. Thankfully, we had none. This house exceeded our expectations.

  • Submitted: Oct 24, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Bloomington IN

Peaceful retreat on Western Bay/Mt Desert Island

  • 5 of 5

Four friends spent 3 great days at Windaway in mid-October. The house had all the amenities we needed including everything for a lobster dinner. The house is large enough we could spread out and the view from the windows out to the bay were sublime. All the bedrooms had enough space for our clothes and the bedding kept us warm during the cool nights. The kitchen/dining room had a pellet stove which was extremely easy to turn on to take the chill off the mornings. Farmer Matt was most accommodating and gave us good suggestions for places to eat in th area. Don’t just go to Bar Harbor and the main area of Acadia - check out other parts of the island and the park. We really enjoyed driving to the Schoodic Peninsula. Get a lobster and take it home to steam. Go to Sweet Peas and have some of Matt’s incredible oysters, too. Spend time in the early morning at the water watching the birds and water fowl. We plan to come back either together or with our families.

  • Submitted: Oct 17, 2017
  • Stayed: October 2017
  • Source: HomeAway
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Nearest Airport
5 Miles
Bar Harbor Airport
Nearest Beach
In front of Windaway
Car: necessary

Windaway House, is located on the Windaway estate. Recent renovations have preserved the 1950s rustic charm of this house, and have added clean, modern comforts such as brand new beds, new flooring, appliances, furnishings, and decor. For larger family groups or retreats, the Windaway Loft can also be rented, which is a connected, brand new 2 bedroom apartment with a gorgeous balcony offering amazing views. Windaway Estate has direct/private access to a serene, rocky Maine beach on Western Bay. Located on a quiet road just a half mile from the bridge connecting the island to the mainland, Windaway offers a convenient gateway location from which to explore all of the beautiful towns and villages on MDI. Acadia National Park is spread all over the island -- the closest trail head is only a few miles away! While it is certainly best to bring a car to MDI, just down the road you can hop on the Island Explorer, which is free and takes you all around the Island and through Acadia National Park. The Island Explorer runs from early morning till late evening. It even has a bike rack!

Windaway Estate, comprising the Windaway Summer House and the Windaway Loft is the perfect, gorgeous setting and location for your MDI vacation!


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Property Damage Protection $59
Pet Fee $75 + Tax

Our rentals are by the week only, and are strictly on a Saturday to Saturday basis. Check in is at 4pm, and Check out is at 10am.

Manager's Cancellation Policy

Please ask the manager or check their rental agreement when booking the property.