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Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!

Holiday home in Boothbay Harbor with kitchen and balcony

Photo gallery for Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!

Welcome Aboard!
You are right on the Harbor
Cockpit entrance
Relax in the saloon
Interior

Reviews

10 out of 10
Exceptional
3 bedrooms1+ bathroomSleeps 50.1 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Outdoor space
  • Parking available

Explore the area

View map
Boothbay Harbor, ME
  • Place, Fisherman's Memorial Park
    ‪5 min walk‬
  • Place, Barrett Park
    ‪8 min walk‬
  • Place, Boothbay Harbor Marina
    ‪11 min walk‬
  • Airport, Wiscasset, ME (ISS)
    ‪32 min drive‬

Rooms & beds

3 bedrooms (sleeps 5)

2 Bunks At Front of Boat

2 Single Bunk Beds

Master Bedroom Aft

1 Queen Bed

Side Rm Adjoins AFt

1 Single Bunk Bed

1 bathroom, 1 half bathroom

Bathroom 1

Bathroom 2

Spaces

Deck or patio
Kitchen
Balcony

About this property

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.

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Amenities

Kitchen
Washing machine
Dryer
Air conditioning
Outdoor space
Parking available

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House Rules

Check in after 4:00 PM
Minimum age to rent: 30
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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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 and a first aid kit

About the area

Boothbay Harbor

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.
Map
Boothbay Harbor, ME

What's nearby

  • Fisherman's Memorial Park - 5 min walk - 0.5 km
  • Barrett Park - 8 min walk - 0.7 km
  • Boothbay Harbor Marina - 11 min walk - 1.0 km
  • Burnt Island Living Lighthouse - 13 min walk - 1.1 km
  • Opera House at Boothbay Harbor - 16 min walk - 1.4 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
  • ‪Harborside 1901 Bar & Grill - ‬15 min walk
  • ‪Tugboat Inn - ‬20 min walk
  • ‪Brisetto’s Second Cup - ‬4 min drive

Frequently asked questions

Is Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

On-site parking is available at the property.

What time is check-in at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

Check-in begins at 4:00 PM.

What time is check-out at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

Checkout is at 10:00 AM.

Where is Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! located?

Situated in Boothbay Harbor, this holiday home 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).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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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

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

About the host

Hosted by Audrey Miller

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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