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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 2
Space 600 sq ft
Property type villa
Minimum Stay 7 nights


About the property

2 bed, 1 bath, sleeps 5

The aim and mission of the Windaway Estate is to celebrate the natural, native landscape of Mount Desert Island, and provide a YEAR ROUND peaceful, beautiful, and FUN spot for family vacations, romantic getaways, and special retreats. The Windaway Loft, part of the Windaway estate, is a perfect choice for a small family or up to 2 couples who want an oceanfront vacation in Bar Harbor, but prefer to stay just far enough away from the craziness of town. Available by itself or in conjuction with Windaway Summer House (vrbo #507910), Windaway Loft is a 2 story, apartment type dwelling. Once the attached garage of the Windaway summer house, it has very recently been lovingly renovated into a truly delightful, light filled, modern addition to the retreat like quality of the Windaway Estate. Hi Speed Wifi internet is included in the rental rate. There are 2 bedrooms, each with a brand new beds (one with a king, one with 2 twins), along with a bathroom with washer/dryer on the first floor. Linens and towels are new, high thread count and high quality. On the second floor, the open concept living/kitchen/dining area and large deck (with a grill and picnic table) offer exceptional views of the cranberry field and the ocean beyond. All appliances and furnishings are new, and tastefully coordinated. The seating is very comfortable and takes advantage of the views. 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.

During the 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 oceanside fire pit area and absorb the Maine night sky complimented by the sounds of the ocean. We love and welcome pets but charge a $75 fee for extra 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 21, 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 villa 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 villa 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 Villa Accommodation and Amenities

Property Type:
  • villa
  • Guests provide their own meals
  • Housekeeper Included
Floor Area:
  • 600 sq ft
House Rules:
  • Max. occupancy: 5
  • pets considered
  • Events Allowed
  • children welcome
  • non smoking only
Location Type:
  • Beachfront
  • Ocean View
  • Oceanfront
  • Adventure
  • 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
  • Coffee Maker ...
  • Dishes & Utensils ...
  • Dishwasher
  • Kitchen ...
  • Microwave
  • Oven
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Dining ...
  • Dining Area
  • seating for 6 people
  • 1 Bathroom
  • Bathroom 1 - toilet , shower
  • modern fixtures, washer/dryer, stall shower
  • 2 Bedrooms, Sleeps 5
  • Bedroom 1 - 1 king
    Bedroom 2 - 2 twin/ single
  • Closet, bureau, high quality linens
  • Books
  • Satellite / Cable ...
  • Stereo ...
  • Television
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • wheelchair inaccessible
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • recreation center
  • restaurants
  • water parks
  • winery tours
  • zoo
Leisure Activities:
  • antiquing
  • beachcombing
  • bird watching
  • boating
  • eco tourism
  • horseback riding
  • miniature golf
  • scenic drives
  • shelling
  • 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
  • fishing
  • golf
  • hiking
  • kayaking
  • mountain biking
  • mountain climbing
  • rock climbing
  • sailing
  • 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 -
(22 traveler reviews)

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Oceanfront Mount Desert Island Retreat
average rating of 4.909091 based on 22 reviews
Arlington, MA

Peace, quiet and nearby lobster; Goldilocks distance to Acadia and Bar Harbor

  • 5 of 5

The Windaway Loft suited us prefectly. It’s well-appointed (nice sofas and a great, modern kitchen) and has an upside-down floorplan with a great deck looking out to Alley Island on the NW corner of MDI. That location was especially beneficial during our visit (June 2018) because it allowed us to get to Acadia’s Cadillac Mtn. entrance and into Bar Harbor’s village district area in ~20 minutes without having to traverse the roadwork underway on RT 3. We came with plans to eat in every night — which we did — but that didn’t mean that we actually cooked every night, because a great lobster pound (Travellin’ Lobster) is just minutes away. That said, the kitchen is excellent and very, very well-equipped. We’ll be back.

  • Submitted: Jun 17, 2018
  • Stayed: June 2018
  • Source: VRBO, from HomeAway
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Very nice place to stay on MDI

  • 5 of 5

The Windaway Loft is a lovely little place in a great location on MDI. It's very clean and comfortable. It has a nice view and is an easy walk to the ocean. The kitchen is well supplied.

It also has some features that other rentals miss. They make recycling very easy and collect redeemables for a good cause. You can't help but feel good when you realize the roof is covered in solar panels. Plus, the owner: Farmer Matt is a very friendly guy who offers any assistance you might want.

  • Submitted: Jun 10, 2018
  • Stayed: June 2018
  • Source: HomeAway
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Super clean and private. Great location to access the park and downtown BarHarbor.

  • 5 of 5

This is our 3rd trip to Bar Harbor using VRBO and we liked this place the best. Very clean and private. Awesome location, easy to get anywhere on the island. Highly recommend this rental.

  • Submitted: Apr 22, 2018
  • Stayed: April 2018
  • Source: HomeAway
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Excellent peaceful location close enough to hit all the hot spots but be out of the busy area

  • 5 of 5

Our stay at Farmer Matt's Windaway Loft could have only been better if the weather was a tad warmer. Our host and accommodations were perfect for our family of four. Farmer Matt was willing to show the kids around the farm as well as introduce us to Kevin. The location of this property is perfect because it is close enough to everything, but it's still far enough away that you aren't in the middle of the traffic. We hope to return again.

  • Submitted: Apr 19, 2018
  • Stayed: April 2018
  • Source: VRBO, from HomeAway
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Douglaston, New York


  • 5 of 5

Wow what a beautiful well maintained place to stay. We were there in the off season (April 2018) so was a little concerned if the place would be cold and maybe dusty if no one had stayed there in months. How wrong was I, this is one of the cleanest properties we have ever stayed in and nice a cozy considering we had quite cold weather. Matt has done a fantastic job, beds were very comfortable, linens awesome and a well stocked kitchen should you choose to cook. The views from the living are even more beautiful than the pictures, one can see the sun setting right from the deck. The walk to the beach is about 2 minutes and you get to interact with the oyster farmers who are harvesting oysters on a daily basis – tough cold job in the winter months! The location is great because you are about 20-30 minutes from most access points on Acadia but also for supermarkets you are also 20 minutes in the opposite location. Highly recommend this place and this will be our spot to stay when we come back to Acadia.

  • Submitted: Apr 9, 2018
  • Stayed: March 2018
  • Source: HomeAway
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  • 5 of 5

Perfect accommodations for the two of us. The balcony/deck gives a great place to watch

sunsets and the ocean inlet. The surrounding woods give peace, serenity and privacy. Easy drive to Bar Harbor sites and Acadia National Forest. Wonderful vacation!!

  • Submitted: Oct 15, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
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Nearest Airport
5 Miles
Bar Harbor Airport
Nearest Motorway
40 Miles
Car: necessary

Windaway apartment is located on the Windaway estate. The apartment itself is a brand new renovation, complete with high end appliances and furnishings. The apartment can be rented by itself, or in conjunction with the Windaway Summer House, which is connected. 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.