Entire home

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!

Marina
3 bedrooms, desk, WiFi, bed sheets
Interior
Fridge, microwave, stovetop, coffee/tea maker
Marina

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 50 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

Room options

About the area

Boothbay Harbor

At this holiday home you'll be within just a 10-minute stroll of Fisherman's Memorial Park and Linekin Bay. Highlights at this holiday home include a kitchen, a washing machine and a balcony. .Home features 1.5 bathrooms, a TV and a coffee/tea maker. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. .Sights within a 20-minute walk of this Boothbay Harbor holiday home include Opera House at Boothbay Harbor and Barrett Park.

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
  • ‪Footbridge Brewery - ‬15 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Similar properties

Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Kitchen

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

Bedrooms

  • 3 bedrooms
  • Bedsheets provided

Bathroom

  • 1.5 bathrooms
  • Bathtub
  • Towels provided

Entertainment

  • TV with cable/satellite channels

Outdoor areas

  • Balcony
  • Barbecue grill

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

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

General

  • Unit size: 1 square foot

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 and a first aid kit
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. 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 and a first aid kit in all accommodation.

Property is also known as

c52b86e8-3c4b-41c8-8367-3bcd0318543c

Frequently asked questions

Are there any beaches close to Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

The closest beach to Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! is Grimes Cove Beach (4 km).

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

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

No, Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! does not offer an airport shuttle service.

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

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

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

No, pets are not allowed.

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

10/10 Excellent

Andy W.

Liked: Cleanliness
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