Entire home

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

Vacation home in Boothbay Harbor with kitchen and balcony

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Marina
Fridge, microwave, stovetop, coffee/tea maker
Interior
Marina
Interior

Reviews

10 out of 10
Exceptional

Entire home

3 bedrooms2 bathroomsSleeps 51 sq ft

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Air conditioning
  • Barbecue grill
  • Kitchen

Explore the area

View in a 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 neighborhood

Boothbay Harbor

This vacation home places you within a 10-minute stroll of Fisherman's Memorial Park and Linekin Bay. The vacation home includes a kitchen, a balcony, and a refrigerator.

What's nearby

  • Fisherman's Memorial Park - 5 min walk - 0.3 miles
  • Barrett Park - 8 min walk - 0.5 miles
  • Boothbay Harbor Marina - 11 min walk - 0.6 miles
  • Burnt Island Living Lighthouse - 13 min walk - 0.7 miles
  • Opera House at Boothbay Harbor - 16 min walk - 0.9 miles

Getting around

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

Restaurants

  • ‪Tugboat Inn - ‬20 min walk
  • ‪Boothbay Lobster Wharf - ‬4 min walk
  • ‪Harborside 1901 Bar & Grill - ‬15 min walk
  • ‪McSeagull’s Restaurant - ‬16 min walk
  • ‪Brisetto’s Second Cup - ‬4 min drive

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!

THIS HOME RENTS WITH A 3-NIGHT MINIMUM, JUNE - SEPTEMBER

Cottage Connection is proud to offer one of the most unique vacation rental experiences we have offered in our 30 years! We invite you to experience the beauty and wonder of life on the water in Boothbay Harbor by staying on a sailboat!  Best of all, no boating experience is required to enjoy this vessel.  As the old Mainers would say, this boat "don't go nowhere, stays right heah!" (Bert and I)  What's more, you're securely docked at a marina Carousel Marina with a restaurant, laundry, showers, water taxi, and more! Please get in touch with our office for a full list of amenities at the marina which is under new vibrant ownership. You're also an easy walk into the head of Boothbay Harbor with all its shops, restaurants, and boat trips. Enjoy all the amenities of a seaside cottage but with a close-up view of the Harbor. Not suitable for children under 12. Sorry, no parties or events and no overnight guests without approval.

WindSong, a 42-foot ketch sailboat, is ready for you to relax and enjoy harborside living surrounded by beautiful wooden decks, bulkheads, and ceilings with plenty of headroom, all in air-conditioned comfort.  There is space for up to five guests but just as nice for just 2 people (romantic getaway?). The private aft bedroom features a queen-sized bed with its own head (toilet) and entry to the galley (kitchen) and salon (living room/dining area). The forward bedroom has two single berths and its own toilet. The salon features cushioned seating, a table for dining and doing puzzles, etc., with a smart TV mounted on the wall, and WIFI. The forward cabin offers two stacked berths and a half bathroom.  You will be showering at the Marina, not on the boat.

The galley (kitchen) has a sink, induction hot plate, microwave, and refrigerator/freezer. The marina also has a nice restaurant and bar. The boat has heat and air conditioning.  The on-the-rail propane grill on deck makes cooking dinner a fun experience. A couple of teak deck chairs for the aft deck are perfect for enjoying the sunsets and the harbor views while relaxing with your favorite beverage at the day’s end.
Solar lights on the railings make for good lighting coming and going from the boat along with lights on the stairs from the boat to the dock.
We suggest renting kayaks or bringing your own to explore the harbor. Or, take a schooner ride, fishing trip, sunset cruise, or whale watch all of which are available right at your fingertips!  Bring your bikes or rent electric bikes in town!
Parking is provided for one vehicle only.  Additional parking is available at the Cottage Connection office.
Beds: (1) Queen, (2) Twin, (1) Twin
Baths: (1) 1/2 (Shower only), (1) Water Closet
Linens included? Yes, linens and towels are included in your reservation
Dogs allowed? Sorry, no pets are allowed here!
This boat is not suitable for children under 12. Safety is a top priority.
The vacation home is air-conditioned and features a kitchen, 1.5 bathrooms, and a balcony, and there's space to spread out with 3 bedrooms. Other standard amenities include a washing machine, a coffee maker, and a desk.

Similar properties

Property amenities

Internet

  • Available in the house: WiFi

Parking and transportation

  • Parking on site

Kitchen

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

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

  • Smoking not allowed

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 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 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
  • 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, and a first aid kit.

Property is also known as

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

Frequently asked questions

What is there to do around this vacation home?

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

Will I be able to park at this vacation home?

No, this vacation home doesn't offer parking.

Is this vacation home associated with a casino?

No, this vacation home is not connected to a casino.

Is there an indoor pool at this vacation home?

No, there is no indoor pool at this vacation home.

What amenities will couples enjoy at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

Amenities at this vacation home that appeal to couples include a kitchen in each accommodation with kitchens in some.

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

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

Does this vacation home provide breakfast?

No, this vacation home doesn't offer breakfast.

Does this vacation home allow pets to stay for free?

No, pets aren't allowed at this vacation home.

Are there connecting rooms at this vacation home?

No, there aren't connecting rooms at this vacation home.

How close is the airport from this vacation home?

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

Are there rooms with balconies at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!?

Yes, every accommodation at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! comes with a balcony.

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