Entire house boat

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

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

Interior
Coffee/tea maker, fridge, microwave, stovetop
3 bedrooms, desk, WiFi (free), bed sheets
Interior
Bathtub

Reviews

9.0 out of 10
Wonderful

Entire house boat

3 bedrooms1 bathroomSleeps 5

Popular amenities

  • Ocean view
  • Kitchen
  • Free WiFi
  • Air conditioning
  • Laundry
  • Parking available

Explore the area

View in a map
Boothbay Harbor, ME
  • Place, Fisherman's Memorial Park
    ‪6 min walk‬
  • Place, Boothbay Harbor Marina
    ‪18 min walk‬
  • Place, Opera House at Boothbay Harbor
    ‪1 min drive‬
  • Airport, Wiscasset, ME (ISS)
    ‪28 min drive‬

Room options

About the neighborhood

Boothbay Harbor

This houseboat places you within a 10-minute stroll of Fisherman's Memorial Park and Linekin Bay. Guestrooms at this houseboat include kitchens, refrigerators, and microwaves.

What's nearby

  • Fisherman's Memorial Park - 6 min walk - 0.4 miles
  • Barrett Park - 10 min walk - 0.6 miles
  • Boothbay Harbor Marina - 18 min walk - 1.0 mile
  • Opera House at Boothbay Harbor - 1 min drive - 0.9 miles
  • Boothbay Harbor Memorial Library - 2 min drive - 1.2 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
  • ‪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.
Guests can expect to find free WiFi. Other standard amenities include a kitchen, a refrigerator, and a microwave. Limited housekeeping is available.

Similar properties

Property amenities

Internet

  • Available in the accommodation: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub

Entertainment

  • Books

Outdoor areas

  • Barbecue grill

Laundry

  • Laundry facilities

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

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 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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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, a first aid kit, and a deadbolt lock
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 30

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, a smoke detector, a first aid kit, and a deadbolt lock.

Property is also known as

1081391

Frequently asked questions

What is there to do around this houseboat?

This houseboat in Boothbay Harbor is within a 10-minute walk of Linekin Bay and Fisherman's Memorial Park. You'll also find Opera House at Boothbay Harbor and Barrett Park less than a mile away.

Is parking available on site at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

No, there isn't parking at this houseboat.

Is this houseboat associated with a casino?

No, this houseboat is not connected to a casino.

Is there an indoor pool at this houseboat?

No, there is no indoor pool at this houseboat.

What do couples enjoy most about WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

With a stay at this waterfront houseboat, couples will appreciate amenities like a kitchen in each accommodation plus an ocean view and a kitchen in some.

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

No, there isn't a spa tub at this houseboat.

Does this houseboat provide breakfast?

No, this houseboat doesn't offer breakfast.

Does this houseboat allow pets to stay for free?

No, pets aren't allowed at this houseboat.

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

No, there aren't connecting guestrooms at this houseboat.

How close is the airport from this houseboat?

The closest major airport to this houseboat is Wiscasset, ME (ISS), which is 17.9 mi away (30 minutes by car).

Are there rooms with balconies that I can book at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views.?

No, there aren't any accommodations with balconies at WindSong: A charming 3-bedroom retreat in Boothbay Harbor, ME, near waterfront views..

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

Reviews

9.0

Wonderful

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

8.0/10

Cleanliness

Reviews

Verified review

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
Verified review

8/10 Good

David B.

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