Title: Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&selected=91643014&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire home # Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! ## Photo gallery for Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! ![Marina - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/77de2091.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Marina - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/272f3374.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, stovetop, coffee/tea maker - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/492bde72.jpg?impolicy=resizecrop&rw=297&ra=fit) ![3 bedrooms, desk, WiFi, bed sheets - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/16302ed6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Interior - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/8e130501.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies In the heart of Boothbay Harbor, WindSong awaits as a unique sailboat retreat. Docked at Carousel Marina, this 42-foot ketch offers air-conditioned comfort and beautiful wooden decks. Unwind on the aft deck with teak chairs and propane grill or stroll into town for shops, restaurants, and boat trips. ## Reviews 10 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 5 ## Popular amenities - Kitchen - Washing machine - Dryer - Air-conditioning - Outdoor space - Parking available ## 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. ### Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! Windsong: A Unique Harborside Experience on a 42-Foot Ketch Cottage Connection is proud to offer what may be the most unique vacation rental experience in our 33-year history. We invite you to experience the beauty and wonder of life on the water in Boothbay Harbor by staying aboard Windsong, a 42-foot ketch sailboat. Best of all, no boating experience is required—this vessel is securely docked at a vibrant marina, staying "right heah" so you can enjoy the nautical lifestyle with all the comforts of a seaside cottage. Charming Features Stationary Harborside Living: Enjoy a front-row seat to the harbor’s activity from the comfort of your boat. Windsong is securely moored at Carousel Marina, offering a close-up view of the water and the surrounding fleet. Marina Amenities: Your stay includes access to the marina's facilities, including a restaurant and bar, laundry, and showers. For a fun local experience, you can even hop on the water taxi! Comfort on the Water: Relax in air-conditioned comfort surrounded by beautiful wooden decks, bulkheads, and ceilings with plenty of headroom. Outdoor Deck Space: The aft deck features teak chairs and an on-the-rail propane grill, making it the perfect spot for sunset cocktails and dinner with a view. Modern Salon: The interior "salon" serves as your living and dining area, complete with cushioned seating, a table for dining or puzzles, a Smart TV, and Wi-Fi. Walk-to-Town: Located at the head of Boothbay Harbor, you are just an easy walk away from the town’s diverse shops, restaurants, and boat excursions. NOTE: To ensure safety and the best possible experience, Windsong is not suitable for children under 12\. Please note that while the boat has toilets (heads), the marina's shower house provides the most spacious and comfortable experience. The Details: Minimum Stay: 3-Night Minimum (June - September). BEDROOMS: (1) Queen Bed (Aft Cabin), (3) Twin Berths (Forward areas). Sleeps up to 5. BATHROOMS: (1) Half Bath/Water Closet on board. Showers are located at the Marina. DOGS PERMITTED? No, pets are not allowed. LINENS & TOWELS INCLUDED? Yes, linens and towels are included in your reservation. Explore the Region Harbor Adventures: With the harbor at your fingertips, you can easily rent a kayak or board a local schooner for a sunset cruise or whale-watching trip. Carousel Marina: Take advantage of the on-site restaurant and bar for a convenient and delicious meal without leaving the docks. Downtown Boothbay Harbor: Walk into town to explore the historic footbridge, local art galleries, and the bustling waterfront shops. Parking: Parking is provided for one vehicle at the marina; additional parking is available at the Cottage Connection office. Book your unique harborside escape on Windsong today! COTTAGE CONNECTION Vacation Rentals. Privately Owned. Professionally Managed. Trusted since 1993\. Cottage Connection was one of the first vacation rental companies in the Midcoast region of Maine. Since being founded by Jeff and Audrey Miller in 1993, Cottage Connection has been trusted by homeowners and vacationers alike to connect each family with the perfect vacation cottage. ## Property amenities ### Internet - Available in the house: WiFi ### Parking and transport - Parking on site ### Kitchen - Coffee/tea maker - Cookware, dishware, and utensils - Hob - Microwave - Refrigerator ### Bedrooms - 3 bedrooms - Bedsheets provided ### Bathroom - 1.5 bathrooms - Bathtub - Towels provided ### Entertainment - TV with cable/satellite channels ### Outdoor areas - Balcony - Barbecue grill ### Laundry - Laundry facilities - Washing machine ### Work spaces - Desk ### Comfort - Air conditioning - Heating ### Pets - No pets allowed ### Suitability/Accessibility - Smoke-free property ### 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) - First aid kit - Fire extinguisher ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/12000000/11900000/11898600/11898505/aea19254.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Tugboat Inn Boothbay Harbor - Hot tub - Parking included - Free Wi-Fi - Restaurant 9.0 Wonderful 1,000 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=11898505&PinnedHotelID=11898505&HadPinnedHotel=true®ionId=-1&adults=2) ![Windward Premium Harbor View King | Premium bedding, Tempur-Pedic beds, minibar, iron/ironing board](https://images.trvl-media.com/lodging/116000000/115890000/115887700/115887651/w2999h1999x1y1-a8064398.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Topside Inn Boothbay Harbor - Breakfast included - Parking included - Free Wi-Fi - Air-conditioning 10 Exceptional 88 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=115887651&PinnedHotelID=115887651&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property – evening/night](https://images.trvl-media.com/lodging/6000000/5380000/5378100/5378086/b42adef4.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Fishermans Wharf Inn Boothbay Harbor - Parking included - Free Wi-Fi - Air-conditioning - Gym 8.6 Excellent 891 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=5378086&PinnedHotelID=5378086&HadPinnedHotel=true®ionId=-1&adults=2) ![Panoramic Room, 1 King Bed, Balcony, Ocean View (Pier Building) | Terrace/patio](https://images.trvl-media.com/lodging/3000000/2130000/2130000/2129923/b7d35423.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Smuggler's Cove Inn East Boothbay - On private beach - Pool - Breakfast included - Pet-friendly 9.0 Wonderful 451 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=2129923&PinnedHotelID=2129923&HadPinnedHotel=true®ionId=-1&adults=2) ![Theatre show](https://images.trvl-media.com/lodging/1000000/900000/894100/894021/8017bb8a.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Flagship Inn and Suites Boothbay Harbor - Pool - Pet-friendly - Parking included - Free Wi-Fi 8.0 Very good 1,001 reviews £94 includes taxes & fees 8 Mar - 9 Mar [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&selected=894021&PinnedHotelID=894021&HadPinnedHotel=true®ionId=-1&adults=2) ![Superior Room, 1 King Bed | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/96000000/95160000/95153300/95153213/53cadc43.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### The Thistle Inn Boothbay Harbor - Parking included - Free Wi-Fi - Restaurant - Air-conditioning 7.6 Good 86 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=95153213&PinnedHotelID=95153213&HadPinnedHotel=true®ionId=-1&adults=2) ![Front of property](https://images.trvl-media.com/lodging/2000000/1210000/1209100/1209081/c8b83a50.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Harbour Towne Inn on the Waterfront Boothbay Harbor - Breakfast included - Parking included - Free Wi-Fi - Air-conditioning 9.6 Exceptional 78 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-21&endDate=2026-03-22&selected=1209081&PinnedHotelID=1209081&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/25000000/24330000/24327300/24327233/c3c5b378.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Pet Friendly-Steps from All-Harbor View Apt Heart of Boothbay Harbor's Downtown. 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The provision of housing is linked to their trade, business or profession. 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 and a first aid kit 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 If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### Property is also known as c52b86e8-3c4b-41c8-8367-3bcd0318543c ## About the area Boothbay Harbor is home to this holiday home. Boothbay Region Historical Society Museum and Opera House at Boothbay Harbor are cultural highlights, and some of the area's attractions include Maine State Aquarium and Coastal Maine Botanical Gardens. Boothbay Railway Village and Dolphin Mini Golf are also worth visiting. [Visit our Boothbay Harbor travel guide](https://www.expedia.co.uk/Boothbay-Harbor.dx6057298) [View more Holiday homes in Boothbay Harbor](https://www.expedia.co.uk/Boothbay-Harbor-Private-Holiday-Homes.d6057298-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![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%7C43.84402%2C-69.62641&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=9z38ShRKAdN--IxMhweFGJa8w9M=) Boothbay Harbor, ME ### What's nearby - ![Barrett's park in Boothbay Harbor, Maine ](https://images.trvl-media.com/place/6186113/39f3bda3-dc2f-4eb9-a9d4-db795ce9a957.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Barrett Park 8 min walk \- 0.5 miles - ![Boothbay Harbor Maine](https://images.trvl-media.com/place/6186217/beecd738-62a0-40fa-96f1-5f28f019cb34.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Boothbay Harbor Marina 11 min walk \- 0.6 miles - Fisherman's Memorial Park 5 min walk \- 0.3 miles - Burnt Island Living Lighthouse 13 min walk \- 0.7 miles - Opera House at Boothbay Harbor 16 min walk \- 0.9 miles ### Getting around - Brunswick Station 49 min drive - Wiscasset, ME (ISS) 30 min drive ### Restaurants - Circle K 3 min drive - Pinkham’s Gourmet Market 4 min drive - Harborside 1901 Bar & Grill 15 min walk - Tugboat Inn 20 min walk - Footbridge Brewery 15 min walk ## Frequently asked questions ### Is Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! pet-friendly? ### How much is parking at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### What time is check-in at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### What time is check-out at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### Where is Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! Reviews ## Reviews ### 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.co.uk/lp/b/content-guidelines) 10 - Excellent 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Andy W. 17 Aug 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy This was an interesting adventure. First, I can't say enough about the rental company, they are very responsive and reached out numerous times to make sure all was well. Also the people at the marina were very nice and helpful. We have a lot of powerboat experience but not much with sail boats. The Windsong is a beautiful boat and well appointed. It however did take some getting used to as you need to take time to learn where everything is on the boat, how the systems work and where to store your stuff. Once we settled in, we were able to really relax and enjoy the beautiful harbor and setting. The weather was fantastic and just sitting in the cockpit relaxing, enjoying a beverage and watching all the boats was like therapy. Location is perfect too, not right in the hustle and bustle of the main commercial section of the harbor so you're not disturbed, but a very short walk to all the restaurants and shops. I have travelled extensively in my work and private life and am tired of hotels, condos, etc.... this was truly a unique experience, and the boat made the trip unforgettable. ##### Andy W. 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