Entire home
Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!
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Reviews
1010 out of 10
Exceptional
Entire home
3 bedrooms2 bathroomsSleeps 50 sq m
Popular amenities
- Dryer
- Parking available
- Washer
- Air conditioning
- Barbecue grill
- Kitchen
Explore the area

Boothbay Harbor, ME
- Boothbay Harbor MarinaPlace, Boothbay Harbor Marina11 min walk
- Opera House at Boothbay HarborPlace, Opera House at Boothbay Harbor16 min walk
- Carousel Music TheaterPlace, Carousel Music Theater3 min drive
- Wiscasset, ME (ISS)Airport, Wiscasset, ME (ISS)32 min drive
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About the area
Boothbay Harbor
With a stay at this vacation home in Boothbay Harbor, you'll be within a 10-minute walk of Fisherman's Memorial Park and Linekin Bay. .This vacation home is 0.5 mi (0.9 km) from Barrett Park and 1.2 mi (1.9 km) from Boothbay Region Land Trust.
What's nearby
- 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
- Carousel Music Theater - 3 min drive - 2.5 km
- Coastal Maine Botanical Gardens - 8 min drive - 6.8 km
Getting around
- Brunswick Station - 49 min drive
- Wiscasset, ME (ISS) - 30 min drive
Restaurants
- Circle K - 3 min drive
- Tugboat Inn - 20 min walk
- Boothbay Lobster Wharf - 4 min walk
- Harborside 1901 Bar & Grill - 15 min walk
- McSeagull’s Restaurant - 16 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!
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.
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.
Make yourself comfortable in this air-conditioned vacation home, featuring a kitchen with a refrigerator and a stovetop. There's a private balcony. Conveniences include a desk and a microwave.
Guests will find features like onsite parking.
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 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
Pets
Pets not allowed
Children and extra beds
Children are welcome
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
Property is also known as
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