Top-rated for comfort — guests feel right at home here.
Garage parking available
Enjoy the convenience of garage parking - a rare offering in the area.
Discover nearby landmarks
Walk to Bailey Island Bridge
3 bedrooms2 bathroomsSleeps 6
Popular amenities
Garage parking available
Kitchen
Washing machine
Barbecue
Deck or patio
Free Wi-Fi
Explore the area
Bailey Island, ME
Cobwork Bridge
Place, Cobwork Bridge
‪10 min walk‬
beach near Channel View Lane
Place, beach near Channel View Lane
‪11 min walk‬
Bailey Island Bridge
Place, Bailey Island Bridge
‪15 min walk‬
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
About this property
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home
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 and panoramic ocean view. 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), Sundrenched (serving lunch and dinner), and Bailey Island General Store (convenience store).
Spend your days relaxing by the sea, exploring the shore, sailing out of Cook's Lobster on the Schooner Alert (70-foot tall ship), 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.
Sorry, pets are not allowed at The Overlook.
Bed types/descriptions: 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
Bathroom setup/description: First Floor- Full Bath with Shower/Tub Combo Second Floor- Full Bath with Tile Shower
Air Conditioning: No Beach/Water Access: Direct, on property via private stairs, rocky/pebbly shoreline Beach Towels: Not included Departure Cleaning: Included Cable TV: Uses Xfinity Stream app on TV for cable entertainment channels, Xumo Play app for Live streaming news channels Closest Shopping Village: Brunswick, 20min away Coffee Maker: Yes, regular drip Dishwasher: Yes Grill: Gas Grill available, Propane provided Heat Source: Forced hot air Internet Access: Yes, Xfinity Cable Internet and WiFi Linens & Bath Towels: Included, beds are made prior to guest arrival and towels remain in their sanitized packaging, placed on each bed Lobster Pot: Yes Outdoor Firepit: No Parking: 2 cars Stairs to Water: Yes Trash Removal: Included, picked up weekly (for multi-week stays) or upon departure TV: Smart TV in Living Room Usable Fireplaces: No (woodstove in house is NOT for guest use) Washer & Dryer: Yes, located first floor Water Frontage: Direct ocean frontage Water Source: Well water with filtration/softener system, bottled drinking water recommended
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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 Paddleworks are also worth visiting. Discover the area's water adventures with sailing, fishing and swimming nearby, or enjoy the great outdoors with hiking.
beach near Channel View Lane - 11 min walk - 1.0 km
beach near Garrison Cove Road - 13 min walk - 1.1 km
Bailey Island Bridge - 15 min walk - 1.3 km
beach near Water Cove - 18 min walk - 1.5 km
Getting around
Brunswick Station - 32 min drive
Portland, ME (PWM-Portland Intl. Jetport) - 67 min drive
Restaurants
‪Cook's Lobster & Ale House - ‬12 min walk
‪Dolphin Marina & Restaurant - ‬33 min drive
‪Bailey Island General Store - ‬9 min walk
‪Morse’s - ‬19 min drive
‪Holbrooks Lobster Wharf - ‬24 min drive
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.
How much does it cost to stay at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?
As of 25 June 2026, prices found for a 1-night stay for 2 adults at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home on 13 Sept 2026 start from AU$1,430, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
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.
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.
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.
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.
Danita K.
Stayed 3 nights in Jul 2025
From a partner site
10/10 Excellent
Ervin B.
30 June 2025
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.
Ervin B.
From a partner site
10/10 Excellent
Greg M.
5 Aug 2025
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.
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.
Jennifer T.
Stayed 7 nights in Jul 2024
From a partner site
10/10 Excellent
Austina F.
7 Aug 2025
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!
Austina F.
From a partner site
10/10 Excellent
Polly O.
24 Sept 2024
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.
Polly O.
From a partner site
10/10 Excellent
Bev B.
29 July 2024
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
Bev B.
From a partner site
10/10 Excellent
Ervin B.
7 July 2024
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!
Ervin B.
From a partner site
10/10 Excellent
Cathy C.
10 June 2024
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!
Cathy C.
From a partner site
10/10 Excellent
Ervin B.
27 Aug 2023
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.
Ervin B.
From a partner site
10/10 Excellent
Tanya B.
25 July 2023
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
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.