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 ![Property grounds - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/1ffb0aea.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Exterior detail - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/0e3016ad.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Terrace/patio - The Overlook- Enjoy stunning sunsets from this well-appointed Bailey Isl home (Bailey Island)](https://images.trvl-media.com/lodging/92000000/91440000/91433800/91433736/4cf18f30.jpg?impolicy=resizecrop&rw=297&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) ![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/ae1dfd41.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 ![Exterior](https://images.trvl-media.com/lodging/76000000/75720000/75712200/75712176/b8ca61b8.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=2025-12-27&endDate=2025-12-28&selected=75712176&PinnedHotelID=75712176&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34180000/34171600/34171548/c88881cb.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=2025-12-27&endDate=2025-12-28&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. Ask a question ## 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 travellers 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.[More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 16 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10/10 Cleanliness ## Reviews ### 10/10 Excellent #### Michelle R. Sep 14, 2024 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 ##### Michelle R. Stayed 4 nights in Sep 2024 ### 10/10 Excellent #### Danita K. Jul 29, 2025 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. ![](https://a.travel-assets.com/ugc/hotel-reviews/cdd38e41-0ab0-4311-9b86-6687575a6915-1753806264205.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/1a4a77e4-2e3f-406c-93eb-c46f9dd41378-1753806262007.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/8bf12016-9195-4708-8fdf-cb8ed432ad56-1753806264640.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ![](https://a.travel-assets.com/ugc/hotel-reviews/cb1288d8-c978-447c-86dd-bd6803dfa66e-1753806265959.jpg?impolicy=resizecrop&rw=204&ra=fit&q=high) ##### Danita K. Stayed 3 nights in Jul 2025 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Ervin B. Jun 30, 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. ### 10/10 Excellent #### John F. Aug 3, 2024 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. ##### John F. Stayed 7 nights in Jul 2024 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Greg M. Aug 5, 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. ##### Greg M. ### 10/10 Excellent #### Matthew D. Aug 21, 2024 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. ##### Matthew D. Stayed 7 nights in Aug 2024 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Austina F. Aug 7, 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. ### 10/10 Excellent #### Jennifer T. Jul 23, 2024 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. ##### Jennifer T. Stayed 7 nights in Jul 2024 This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Polly O. Sep 24, 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Bev B. Jul 29, 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Ervin B. Jul 7, 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Cathy C. Jun 10, 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Ervin B. Aug 27, 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. This review comes from a trusted partner site and has not been verified. ### 10/10 Excellent #### Tanya B. Jul 25, 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 ##### Tanya B. ### 10/10 Excellent #### Paul G. Sep 24, 2019 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. ##### Paul G. 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