Airport, Portland, ME (PWM-Portland Intl. Jetport)
68 min drive
Room options
About the neighborhood
Bailey Island
This vacation home places you next to Casco Bay and within a 15-minute walk of Bailey Island Bridge. The vacation home includes a kitchen, a patio, and a dining area.
LL Bean Flagship Store - 44 min drive - 31.4 miles
Getting around
Brunswick Station - 32 min drive
Portland Intl. Jetport Airport (PWM) - 67 min drive
Restaurants
Dolphin Marina & Restaurant - 33 min drive
Erica's Seafood & Lobster Shop - 32 min drive
Cook's Lobster House - 12 min walk
Holbrooks Lobster Wharf - 24 min drive
B.I.G.S. Bailey Island General Store - 9 min walk
About this property
Entire place
You'll have the entire home to yourself and will only share it with other guests in your party.
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
The vacation home is heated and features a kitchen, 2 bathrooms, and a patio. There's space to spread out with 3 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.
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Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
Smoke detector (host has indicated there is a smoke detector on the property)
Fire extinguisher
General
Garden
Unit size: 1,574 square feet
Policies
Check-in
Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25
Check-out
Check-out before 10:00 AM
Special check-in instructions
You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools
Pets
This property doesn't allow pets
Children and extra beds
Children allowed: ages 0-17
Events
No events allowed
Smoking
Smoking is not permitted
Important information
You need to know
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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Check-in: 4:00 PM
Check-out: 10:00 AM
Minimum check-in age: 25
We should mention
Details about charges, deposits, or other important information:
This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
Onsite parties or group events are strictly prohibited.
Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.
Property is also known as
2769-214537
Frequently asked questions
What can I see close to this vacation home?
This vacation home is located in Bailey Island, just steps from Casco Bay. You'll also find Bailey Island Bridge and Cobwork Bridge less than a mile away.
Will I be able to park at this vacation home?
Yes, there is a garage.
Is this vacation home next to a casino?
No, this vacation home is not connected to a casino.
Will I find an indoor pool at this vacation home?
No, there is no indoor pool at this vacation home.
Is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home good for couples?
Amenities that appeal to couples at this waterfront vacation home include a kitchen and a smart TV in each accommodation with some featuring ocean views.
Does The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home have a hot tub?
No, this vacation home doesn't have a spa tub.
Does this vacation home offer breakfast?
No, this vacation home doesn't offer breakfast.
Will this vacation home allow pets to stay free of charge?
No, pets aren't allowed at this vacation home.
Does this vacation home have connecting rooms?
No, this vacation home doesn't feature connecting guestrooms.
How far is the airport from this vacation home?
The closest major airport to this vacation home is Wiscasset, ME (ISS), which is 26.5 mi away (44 minutes by car). Another top airport is Portland Intl. Jetport Airport (PWM), which is around 17.1 mi away.
Are there rooms with balconies that I can book at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home?
Yes, every accommodation at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home comes with a deck with some featuring ocean views.
The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home Reviews
Reviews
10
Exceptional
All reviews shown are from real guest experiences. Only travelers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
Rating 10 - Excellent. 16 out of 16 reviews
10 - Excellent
16
Rating 8 - Good. 0 out of 16 reviews
8 - Good
0
Rating 6 - Okay. 0 out of 16 reviews
6 - Okay
0
Rating 4 - Poor. 0 out of 16 reviews
4 - Poor
0
Rating 2 - Terrible. 0 out of 16 reviews
2 - Terrible
0
10/10
Cleanliness
Reviews
10/10 Excellent
K M.
Sep 17, 2025
Liked: Cleanliness
K M.
Stayed 3 nights in Aug 2025
10/10 Excellent
Danita K.
Jul 29, 2025
Liked: Cleanliness
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.
Danita K.
Stayed 3 nights in Jul 2025
10/10 Excellent
Michelle R.
Sep 14, 2024
Liked: Cleanliness
Wonderful vacation
Gorgeous property and we lucked out with the best weather possible!!! Highly recommend The Overlook and we plan on returning
Michelle R.
Stayed 4 nights in Sep 2024
10/10 Excellent
Matthew D.
Aug 21, 2024
Liked: Cleanliness
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.
Matthew D.
Stayed 7 nights in Aug 2024
10/10 Excellent
John F.
Aug 3, 2024
Liked: Cleanliness
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.
John F.
Stayed 7 nights in Jul 2024
10/10 Excellent
Jennifer T.
Jul 23, 2024
Liked: Cleanliness
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.
Jennifer T.
Stayed 7 nights in Jul 2024
10/10 Excellent
Paul G.
Sep 24, 2019
Liked: Cleanliness
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.