The Overlook

  6 guests
  3 bedrooms
  2 bathrooms
  1574 sq. ft.

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Sleeping Arrangement

Bedroom 1
1 Queen
Bedroom 2
1 Queen
Bedroom 3
1 Queen


Perched on the water's edge, The Overlook offers commanding views of Merriconeag Sound to Casco Bay and its islands. You'll find yourself waiting to watch the sunset every evening, as the sky is painted with stunning hues and the soft light fills every room. The Overlook offers multiple decks with plenty of seating for dining outdoors or simply relaxing by the sea. Beautiful gardens and trees surround the property, offering great privacy, while being within walking distance to all Bailey Island has to offer.

Inside you'll find a well appointed kitchen with everything you'll need to prepare a delicious Maine meal, a beautiful dining room area with two sliding glass doors opening to the deck, and a spacious living room with comfortable furnishings, panoramic ocean views, and a woodstove for chilly nights. The first floor also offers a bedroom with a queen bed and ocean views, as well as a full bathroom with a laundry area just outside. On the second floor you'll find two additional ocean view bedrooms with queen beds and a shared full bathroom with a tile shower. Hardwood and tile floors throughout, modern coastal decor, and an abundance of natural light completes this seaside retreat.

Conveniently located in the West Shore neighborhood of Bailey Island, you'll love being just 0.5mi (8-10min walk) from all of the island's great local restaurants including Cook's Lobster & Ale House (serving lunch and dinner), Morse's Cribstone Grille (serving lunch and dinner), Giant Stairs Seafood Grille (serving breakfast, lunch, and dinner), and Bailey Island General Store (convenience store).

Spend your days relaxing by the sea, exploring the shore, catching the Casco Bay Lines Ferry from Cook's Lobster & Ale House for a cruise to Portland, sailing on Schooner Alert (also leaving from Cook's), or soaking up the sun at Cedar Beach (1mi away) and come home to experience the gorgeous sunset over the bay.

The Overlook is the perfect vacation destination and will surely have you coming back for years to come.

First Floor-
Bedroom with Queen Bed, Closet, and Ocean Views
Second Floor-
Master Bedroom with Queen Bed, Closet, and Ocean Views
Bedroom with Queen Bed, Closet, and Ocean Views

First Floor- Full Bath with Shower/Tub Combo
Second Floor- Full Bath with Tile Shower


  • Located on Bailey Island
  • Ocean Frontage
  • Open Ocean View
  • Ocean Access from Property via Private Stairs
  • Panoramic Ocean Views
  • Sunset Views
  • Non Smoking
  • Spacious Yard
  • Privacy Plantings
  • Multiple Decks Overlooking the Ocean
  • Wireless Internet
  • TV (Located in Living Room)
  • Dishwasher
  • Washer & Dryer



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* Rates are subject to change without notice. Pricing excludes taxes, additional options and fees.
Vacation Rental Standard Pricing       Min Nights


North Andover, US
Reviewed: Aug 22, 2018
Property Manager
The Overlook on Baileys island , Harpswell Maine. Beautiful sunset rise and sunset , view, kitchen, just awesome! Everything was just perfect . Definitely recommend to any family to rent this beautiful home with all the amenities . We will be booking this house next year , its just like home.
Norfolk, US
Reviewed: Aug 14, 2018
Property Manager
The name says it all - the Overlook is perched above a quintessential bit of Maine coast. It has all the comforts of home and a view to die for.
Hampton, US
Reviewed: Jun 24, 2018
Property Manager
Overlook is a very special place beautifully decorated and well maintained. The multiple sun light decks and windows offer great water views with cool breezes. This place and this island makes you forget there is another world out there. My wife and I look forward to be able to return next year. Doug and Joan
Kohler, US
Reviewed: Oct 16, 2017
Property Manager
If you are looking for a true Maine experience in a heaven on earth location, this is it. The Overlook was well appointed, comfortable and well stocked. The sunsets were magnificent. Even though there are other homes nearby the landscape made it a very private oasis!
Reviewed: Oct 12, 2017
This is simply a lovely home in a beautiful setting. Very private with two decks overlooking the water, a great outdoor eating area and views of amazing sunsets. The kitchen is fully equipped. There wasnt a thing we needed that wasnt provided. Bedrooms offer spectacular views of the ocean, the moon, and early morning fishing boats. Beds are so comfortable- we all slept well. We wouldnt consider staying anywhere else next time we come to Maine!
Reviewed: Oct 10, 2017
The place was perfectly clean, the furniture, colors, and linens all added to the sense of quiet and peace. We sat on the deck or ate at the dining room table and always had views of the water. Great restaurants nearby for eating out.


Check-In: Check-in is at our office located at 1624 Harpswell Islands Road, Orr's Island, ME 04066 between 4pm and 5pm on the date of your arrival. If you think you may be arriving later, please contact MaineStay Vacations and we would be happy to make other arrangements for you.

Check-Out: Check-out is at 10am on the date of your departure. We kindly ask that all guests are prompt, as our cleaners have many homes to take care of, especially in the summer months.

Linens: All properties are supplied with pillows and blankets or comforters, they do not come with sheets and towels. You have the option to either bring your own or rent our linen service. This service provides you with bed sheets, towel sets for the maximum number of guests allowed, bath mats, and kitchen towels. Towel sets consist of a bath towel, hand towel, and face cloth, and you have the option rent more towel sets if needed. The linens are professionally cleaned and sanitized between use. Linens will be provided to you when you check in at our office.

Payment: We collect 50% when you reserve and the other 50% is due 30 days prior to your arrival. You will receive a notification via email 3 days prior to the due date as a reminder. We accept Visa, MasterCard, Discover, cash, money orders, traveler's checks, and personal checks. If you pay the deposit with a credit card, we will automatically charge the card on file for the final balance. If you wish to change your form of payment, please don't hesitate to contact us when you receive the balance due notification 3 days prior.

What You Will Find at Our Vacation Rental Properties:

  • Pots & Pans, Including a Lobster Pot
  • Glasses, Wine Glasses, and Coffee Mugs
  • Dinner Plates, Salad Plates, and Bowls
  • Flatware
  • Serving Dishes & Utensils
  • Measuring Cups and Spoons
  • Cooking Dishes & Utensils
  • Mixing Bowls & Cutting Boards
  • Lobster Crackers & Picks
  • Coffee Maker
  • Toaster
  • Tea Kettle
  • Blender
  • Blankets
  • Pillows
  • Mattress Cover
  • Alarm Clock
  • Fan
  • Hand Soap
  • Hair Dryer (at least 1 per house)
  • Table & Chairs
  • Grill & Tools
  • Trash bins
  • Iron & Board
  • Vacuum
  • Basic Cleaning Supplies
If you have specific questions about these items, please contact MaineStay Vacations.

What You Need to Bring to Our Vacation Rental Properties:

Groceries- The nearest grocery stores are in Brunswick and are as follows:
Shaws 147 Bath Road, Brunswick, ME 04011
Hannaford 35 Elm Street, Brunswick, ME 04011
Wal-Mart 15 Tibbetts Drive, Brunswick, ME 04011

Bottled Water- All of our properties have private wells, so you may prefer bottled water.

Soaps & Detergents- We do not provide dish soap, sponges, inside trash bags, paper goods, and toiletries. Some items are left by owners and previous renters and can be used. We recommend that you check the property for these items before purchasing them at your local store.

Paper Towel & Toilet Paper- You will receive a complimentary roll of paper towel and toilet paper when you arrive, as well as a trash bag to get you started, but all guests are responsible for these items during their stay.

Linens- If you did not rent our service, please do not forget to bring sheets, towels, bath mats, and kitchen towels.

Beach Towels- Our linen service does not provide beach towels, so please remember to bring them with you.

Beach Chairs- We do not require our owners to provide chairs for the beach.

Propane Tanks- For our homes with gas grills, all propane tanks are filled at the beginning of the season by owners and we ask our guests to please refill tanks that they empty and we will reimburse you for that expense. PLEASE DO NOT LEAVE EMPTY PROPANE TANKS FOR THE NEXT GUEST.