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.

Miscellaneous
3 bedrooms, desk, free WiFi, bed sheets
Bathtub
Fridge, microwave, stovetop, coffee/tea maker
3 bedrooms, desk, free WiFi, bed sheets

Reviews

10 out of 10
Exceptional

Entire house boat

3 bedrooms1 bathroomSleeps 5

Popular amenities

  • Ocean view
  • Kitchen
  • Free Wi-Fi
  • Air-conditioning
  • Laundry room
  • Outdoor space

Explore the area

View map
Boothbay Harbor, ME
  • Place, Fisherman's Memorial Park
    ‪6 min walk‬
  • Place, Barrett Park
    ‪10 min walk‬
  • Place, Boothbay Harbor Marina
    ‪18 min walk‬
  • Airport, Wiscasset, ME (ISS)
    ‪28 min drive‬

Room options

About the area

Boothbay Harbor

At this houseboat you'll be within just a 10-minute stroll of Fisherman's Memorial Park and Linekin Bay. Highlights at this houseboat include a kitchen, free WiFi and a patio. .Near this Boothbay Harbor houseboat, you'll find Coastal Maine Botanical Gardens.

What's nearby

  • Fisherman's Memorial Park - 6 min walk - 0.6 km
  • Linekin Bay - 10 min walk - 0.9 km
  • Barrett Park - 10 min walk - 0.9 km
  • Boothbay Harbor Marina - 18 min walk - 1.5 km
  • Opera House at Boothbay Harbor - 1 min drive - 1.5 km

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
  • ‪Tugboat Inn - ‬20 min walk
  • ‪Footbridge Brewery - ‬15 min walk
  • ‪The Thistle Inn - ‬19 min walk

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

Property amenities

Internet

  • Available in the accommodation: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Hob
  • Microwave
  • Refrigerator
  • Spices

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub

Living spaces

  • Living room

Entertainment

  • Books

Outdoor areas

  • Barbecue grill
  • Patio

Laundry

  • Laundry facilities

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Limited housekeeping

Location highlights

  • Near a hospital
  • Near the bay
  • Near the ocean
  • On the waterfront

Things to do

  • Birdwatching nearby
  • Fishing nearby
  • Hiking nearby
  • Kayaking nearby
  • Swimming nearby
  • Whale watching 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)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 30

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

  • No pets 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
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, a first aid kit and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit and a deadbolt lock in all accommodation.

Property is also known as

1081391

Frequently asked questions

Are there any beaches close to WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

The closest beach to WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. is Grimes Cove Beach (4 km).

Does WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. have a pool?

No, this houseboat doesn't have a pool.

Is there a free airport shuttle available at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

No, WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views. does not offer an airport shuttle service.

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

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

No, pets are not allowed.

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

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

Verified

10/10 Excellent

Andy W.

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