Title: The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home Waterfront vacation home with kitchen and patio ## Photo gallery for The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home ![Dining - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/37eaba2a.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Dining - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/707a6800.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Beach - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/ef20204f.jpg?impolicy=resizecrop&rw=297&ra=fit) ![3 bedrooms, desk, iron/ironing board, free WiFi - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/e78068ce.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, oven, stovetop - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/58456bf2.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Perched on the water's edge, The Overlook offers commanding views of Merriconeag Sound to Casco Bay and its islands. Beautiful gardens surround the property with plenty of seating for dining outdoors or simply relaxing by the sea, a well appointed kitchen, a spacious living room with comfortable furnishings and panoramic ocean view. ## Reviews 10 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 61574 sq ft ## Popular amenities - Dryer - Washer - Kitchen - Barbecue grill - Outdoor space - Free WiFi ## Add dates for prices Check-in Check-out Travellers ## 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 ## Property amenities ### Internet - Available in the house: Free WiFi ### Parking and transportation - Onsite parking options include a garage ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Microwave - Oven - Refrigerator - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Bathtub or shower - Hair dryer - Shower - Towels provided ### Living spaces - Dining table - Living room - Separate dining area ### Entertainment - Smart TV with cable/satellite channels ### Outdoor areas - Barbecue grill - Garden - Patio ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk - Desk chair ### Comfort - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Tile flooring in public areas - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Location highlights - Near a hospital - Near an outlet shopping mall - Near the ocean - On the waterfront ### Things to do - Golf - Fishing nearby - Golfing nearby - Hiking/biking trails nearby - Sailing nearby - Swimming nearby ### Safety features - 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 ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/76000000/75720000/75712200/75712176/0951468d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Classic Maine cottage set on its own peninsula with stunning views Harpswell - Ocean view - Pool - Kitchen - Washer 10 Exceptional 25 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29&selected=75712176&PinnedHotelID=75712176&HadPinnedHotel=true®ionId=-1&adults=2) ![Interior](https://images.trvl-media.com/lodging/35000000/34180000/34171600/34171548/26172b46.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Charming 3BR, 1.5BA beachfront cottage with multi-level decks Harpswell - 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Parking included - Free WiFi - Restaurant 9.6 Exceptional 557 reviews [](https://www.expedia.ca/Hotel-Search?startDate=2025-12-28&endDate=2025-12-29&selected=75630171&PinnedHotelID=75630171&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Pets not allowed ### Children and extra beds Children are welcome ### 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 ### Property is also known as 2769-214537 ## About the area ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C43.74160%2C-69.99498&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=l99UW9upIEWgz64y_y2utzUgd0c=) Bailey Island, ME #### What's nearby - Cobwork Bridge \- 10 min walk \- 0.9 km - Bailey Island Bridge \- 11 min walk \- 1.0 km - Mackerel Cove \- 19 min walk \- 1.7 km - Bowdoin College \- 32 min drive \- 27.5 km - LL Bean Flagship Store \- 44 min drive \- 50.6 km #### Getting around - Brunswick Station - 32 min drive - Portland Intl. Jetport Airport (PWM) - 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 - ‪B.I.G.S. Bailey Island General Store - ‬9 min walk - ‪Holbrooks Lobster Wharf - ‬24 min drive ## Frequently asked questions ### Is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home pet-friendly? ### What time is check-in at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home? ### What time is check-out at The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home? ### Where is The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. 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