Entire home

The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

Photo gallery for The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home

A wooden deck with two Adirondack chairs facing a calm lake, surrounded by greenery and a clear sky.
A house with a front door, a window with shutters, a mailbox, and a number '63' on the wall.
A bedroom with a bed, dresser, and two lamps.
A spacious living room with a large gray sectional sofa, wooden flooring, a fireplace, and large windows overlooking a body of water.
A kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a window providing natural light.

Reviews

10 out of 10
Exceptional

Highlights

  • Scenic water view
    Relax and unwind with top-rated water views, offering a scenic experience.
  • Garage parking available
    Enjoy the convenience of garage parking - a rare offering in the area.
  • Unmatched views, unforgettable moments
    Guests like the location for the scenic views.
  • Discover nearby landmarks
    Walk to Casco Bay

Popular amenities

  • Patio
  • Barbecue grill
  • Refrigerator
  • Garage parking available
  • Internet
  • Washing machine

Explore the area

View in a map
Bailey Island, ME
  • Place, Casco Bay
    ‪1 min walk‬
  • Place, Cobwork Bridge
    ‪10 min walk‬
  • Place, Bailey Island Bridge
    ‪15 min walk‬
  • Airport, Auburn, ME (LEW-Auburn - Lewiston Municipal)
    ‪58 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Toilet

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Separate dining area
Garden

Add dates for prices

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About the area

Bailey Island

Located in Bailey Island, this holiday home is on the waterfront. Brunswick Naval Aviation Museum and Pickard Theater are cultural highlights, and some of the area's landmarks include Bailey Island Bridge and Cobwork Bridge. Land's End Gift Shop and Ash Cove Pottery are also worth visiting. Discover the area's water adventures with sailing, fishing and swimming nearby, or enjoy the great outdoors with hiking.
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Map
Bailey Island, ME

What's nearby

  • Casco Bay - 1 min walk - 0.0 km
  • Cobwork Bridge - 10 min walk - 0.9 km
  • beach near Channel View Lane - 11 min walk - 1.0 km
  • Bailey Island Bridge - 15 min walk - 1.3 km
  • beach near Merritt House Road - 20 min walk - 1.7 km

Getting around

  • Brunswick Station - 32 min drive
  • Portland, ME (PWM-Portland Intl. Jetport) - 67 min drive

Restaurants

  • ‪Dolphin Marina & Restaurant - ‬33 min drive
  • ‪Cook's Lobster & Ale House - ‬12 min walk
  • ‪Erica's Seafood & Lobster Shop - ‬32 min drive
  • ‪Holbrooks Lobster Wharf - ‬24 min drive
  • ‪Sundrenched - ‬10 min walk

Frequently asked questions

Is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home pet-friendly?

No, pets are not allowed at this property.

What time is check-in at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

Check-in begins at 4:00 PM.

What time is check-out at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?

Checkout is at 10:00 AM.

Where is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home located?

Situated on the waterfront, this holiday home is within a 15-minute walk of Casco Bay, Bailey Island Bridge and Cobwork Bridge. Mackerel Cove and Land's End Gift Shop are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful vacation

Gorgeous property and we lucked out with the best weather possible!!! Highly recommend The Overlook and we plan on returning
Stayed 4 nights in Sep 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house and location

House was very nice for our family of 5. On the water with a great view. Kitchen was well equipped and everything was in good working order. Would definitely stay again.
Stayed 7 nights in Jul 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relax and Enjoy the View

Sunsets, birds, boats, and the sea, magnificent views. Private, hidden, and comfortable place right on the water was perfect for the four of us. We enjoyed every minute of our stay. It's not too far away from many towns like Bath and Boothbay Harbor too.
Stayed 7 nights in Aug 2024
From a partner site

10/10 Excellent

Our 5th year at The Overlook

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: As in prior years, everything was perfect, including the weather.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Clean and exceptionally appointed kitchen

Very clean and comfortable home, with beautiful sunset views. Kitchen is exceptionally appointed. Gorgeous landscaping with cedar wax wings, gold finches and song sparrows flitting about. Lots of Adirondack seating for coastal views with your coffee and book.
Stayed 3 nights in Jul 2025
From a partner site

10/10 Excellent

Perfect Home, Perfect Spot

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I was traveling with older relatives who needed an accessible home right on the water. The home was spectacularly well-furnished and the view before us including a veritable lobster farm was stunning, sunrise to sunset.
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful view, clean and quiet

Such a charming property! The house was super clean, quiet, and felt very private....and the view was amazing! It was mid-July and no AC was needed because of the lovely breeze. There are fans available at the property if needed, but we didn't need them. We were able to launch our paddle boards right from the property at high tide. The house was well equipped - had everything we needed.....we even used the Thyme in the herb garden.
Stayed 7 nights in Jul 2024
From a partner site

10/10 Excellent

Beautiful Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The house is in a great location on Baileys Island and is decorated so you feel comfortable and right at home. There was a lot of outdoor seating for us to watch the water/sunset. The kitchen has everything you will need. It is also really simple to contact management since they text you and are available for any questions. The only downside is if you stay in the hotter months, there is no AC, but they do have fans throughout. I would definitely stay here again!
From a partner site

10/10 Excellent

Our sixth yaer at The Overlook

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Once again, we had a fantastic stay. the cottage has everything we are looking for as far as furnishings, view, privacy, etc.
From a partner site

10/10 Excellent

Wonderful!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a spectacular time at The Overlook. The house was impeccable, and the views are exquisite. Cannot say enough good things.
From a partner site

10/10 Excellent

best of bailey

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: lovely house with fantastic water views from lots of windows. house very clean-lovely bed linens-nice kitchen
From a partner site

10/10 Excellent

2024 Stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: For the fourth year in a row, it was excellent!
From a partner site

10/10 Excellent

Girls weekend

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was perfect, just as described!
From a partner site

10/10 Excellent

Our third stay at The Overlook

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Everything was excellent, except the weather. Even with the rain and clouds, it is still such a beautiful location we enjoy it no matter what.
From a partner site

10/10 Excellent

Wonderful vacation!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We loved everything about the property. Much appreciated the lawn games, indoor games, and having basic spices on hand. Beautiful views, clean and inviting
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Property and Location

The house is very well equipped for travelers, the kitchen has everything you could imagine including a milk steamer for coffee! The setting is wonderful right on the water which create a great canvas for nightly sunsets. Cooks, Morse's and the Giant Stairs restaurants are within walking distance, including the Bailey Island Grocery (BIG's) which serves food from their grill. It is a must to experience BIG's for breakfast and their blueberry pancakes, make sure to order just one because they cover an entire plate...... Great overall experience and the owners have certainly put much thought and care into the property.
Stayed 7 nights in Sep 2019
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Aug 2025
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