Entire house boat

WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.

Photo gallery for WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.

A cabin interior with a bed, wooden walls, and a window with curtains. - WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. (Boothbay Harbor)
A compact kitchen with wooden cabinets, a microwave, a stove, and a sink. - WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. (Boothbay Harbor)
A cabin interior with a round wooden table, floral-patterned bench, a vintage television, and a 'J MAINE' sign. - WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. (Boothbay Harbor)
A marina with various boats docked. - WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. (Boothbay Harbor)
A cabin interior with a wooden bench, a round table with a vase of flowers, a wall-mounted TV, and a sign reading 'MAINE'. - WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. (Boothbay Harbor)
WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. provides laundry facilities and more. Stay connected with free in-room WiFi.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Ocean view
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Laundry room
  • Parking available

Add dates for prices

About this property

WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.

  • 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.

Similar properties

A waterfront property with a dock, a boat, and a multi-story building with balconies.
Tugboat Inn
Boothbay Harbor
  • Hot tub
  • Parking included
  • Free Wi-Fi
  • Restaurant
9.0 out of 10, Wonderful, 1,001 reviews
The price is €166
includes taxes & fees
22 Nov - 23 Nov
Tugboat Inn
Compare similar properties

About the area

Located in Boothbay Harbor, this houseboat is on the waterfront. Boothbay Region Historical Society Museum and Opera House at Boothbay Harbor are cultural highlights, and some of the area's attractions include Coastal Maine Botanical Gardens and Maine State Aquarium. Boothbay Railway Village and Dolphin Mini Golf are also worth visiting. Discover the area's water adventures with kayaking, fishing and swimming nearby, or enjoy the great outdoors with hiking. Visit our Boothbay Harbor travel guide
View more Houseboats in Boothbay Harbor
Map
Boothbay Harbor, ME

What's nearby

  • A picnic table by a river with a stone wall and trees.
    Barrett Park
    10 min walk - 0.9 km
  • A harbor with boats, a dock, and a rocky shoreline with a lobster trap.
    Boothbay Harbor Marina
    18 min walk - 1.5 km
  • Fisherman's Memorial Park
    6 min walk - 0.6 km
  • Opera House at Boothbay Harbor
    1 min drive - 1.5 km
  • Burnt Island Living Lighthouse
    2 min drive - 1.8 km

Getting around

  • Brunswick Station
    49 min drive
  • Wiscasset, ME (ISS)
    30 min drive

Restaurants

  • Coastal Maine Botanical Gardens
    9 min drive
  • Circle K
    3 min drive
  • Kitchen Garden Cafe
    9 min drive
  • Boothbay Lobster Wharf
    4 min walk
  • Tugboat Inn
    20 min walk

Frequently asked questions

Is WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. pet-friendly?

No, pets are not allowed at this property.

How much is parking at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

On-site parking is available at the property.

What time is check-in at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

Check-in begins at 4:00 PM.

What time is check-out at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

Checkout is at 10:00 AM.

Where is WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. located?

Situated on the waterfront, this houseboat is within a 10-minute walk of Fisherman's Memorial Park and Linekin Bay. Barrett Park and Opera House at Boothbay Harbor are also within 1 mile (2 km).

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. Reviews

9.0

Wonderful

8.0

Cleanliness

9.0

Location
Rating 10 - Excellent. 1 out of 2 reviews
Rating 8 - Good. 1 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

Reviews

Verified review

10/10 Excellent

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.
Stayed 3 nights in Aug 2025
Verified review

8/10 Good

Liked: Check-in, communication, location
We enjoyed our stay and appreciate the effort to correct the problem of the non-op refrigerator by placing a temporary mini-fridge, but frankly, the thing was in the way. Not much else that could be done, so appreciated. It would've been nice if the owners had left some space for us to store our few items by removing their personal items - who leaves their toothbrushes, hair products and clothes in a VRBO, much less a boat with little space? Also, please fill the potable water tank before guests get there instead of relying on them to do it - fortunately I found the needed tool that had been left somewhere on the deck and was able to do it. The instructions for the A/C pump/filter and other such items need clarification, especially regarding locations. The marina facilities were excellent and overcame the inconvenience of not being able to use the bathrooms on the boat. The staff there were as friendly as they could be. Alexis with Cottage Connection was always available and helpful and did her best to solve problems - including providing towels when so few were initially available. She was top-notch! We won't return, but did enjoy our stay - just wished for these improvements. I would recommend limiting the listing to no more than 4 people with the space available. Thank you for a charming stay during our vacation.
Stayed 5 nights in Jun 2026