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.