Title: Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! Reviews, Deals & Photos 2026 - Expedia.co.uk [See all properties](http://www.expedia.co.uk/Hotel-Search?regionId=&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) 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 - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/77de2091.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/8e130501.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Marina - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/272f3374.jpg?impolicy=resizecrop&rw=297&ra=fit) ![3 bedrooms, desk, WiFi, bed sheets - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/16302ed6.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Fridge, microwave, stovetop, coffee/tea maker - Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! (Boothbay Harbor)](https://images.trvl-media.com/lodging/92000000/91650000/91643100/91643014/492bde72.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies In the heart of Boothbay Harbor, WindSong awaits as a unique sailboat retreat. Docked at Carousel Marina, this 42-foot ketch offers air-conditioned comfort and beautiful wooden decks. Unwind on the aft deck with teak chairs and propane grill or stroll into town for shops, restaurants, and boat trips. ## Reviews 10 Exceptional ### Entire home 3 bedrooms2 bathroomsSleeps 51 sq ft ## Popular amenities - Kitchen - Washing machine - Dryer - Air-conditioning - Outdoor space - Parking available ## Add dates for prices Check-in Check-out Travellers ## 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. ## 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 ## Similar properties ![Terrace/patio](https://images.trvl-media.com/lodging/81000000/80060000/80054700/80054612/w1024h677x0y46-b504250b.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Woodland ADA Lodge | Spa Access | No Hidden Fees Boothbay Harbor - Pool - Hot tub - Free Wi-Fi - Air-conditioning [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=80054612&PinnedHotelID=80054612&HadPinnedHotel=true®ionId=-1&adults=2) ![Dining](https://images.trvl-media.com/lodging/110000000/109790000/109784500/109784412/2e6480ab.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Available : Book your summer holiday! Boothbay Harbor - Kitchen - Washing machine - Dryer - Air-conditioning 9.8 Exceptional 6 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=109784412&PinnedHotelID=109784412&HadPinnedHotel=true®ionId=-1&adults=2) ![Smart TV, stereo](https://images.trvl-media.com/lodging/104000000/103980000/103974000/103973980/w1380h775x0y1-e8756ecb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Boothbay Harbor Woodland Retreat Boothbay Harbor - Kitchen - Washing machine - Dryer - Pet-friendly 10 Exceptional 6 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=103973980&PinnedHotelID=103973980&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/102000000/101340000/101332500/101332481/c4b3a81d.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Beautifully updated cabin near town & Barrett's Park with deck, BBQ, & W/D Boothbay Harbor - Kitchen - Washing machine - Dryer - Air-conditioning 9.0 Wonderful 2 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=101332481&PinnedHotelID=101332481&HadPinnedHotel=true®ionId=-1&adults=2) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112880000/112875800/112875762/f8132714.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Ambleside in Boothbay Harbor Maine! Perfect for a warm and cozy Gardens Aglow! Boothbay Harbor - Kitchen - Washing machine - Dryer - Free Wi-Fi 10 Exceptional 9 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=112875762&PinnedHotelID=112875762&HadPinnedHotel=true®ionId=-1&adults=2) ![Property grounds](https://images.trvl-media.com/lodging/41000000/40060000/40055300/40055201/cbf16b60.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Spacious and Comfortable Home Next to all the Action! Boothbay - Kitchen - Washing machine - Dryer - Free Wi-Fi 9.8 Exceptional 70 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=40055201&PinnedHotelID=40055201&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/77000000/76040000/76035600/76035591/77b3477c.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Smuggler's Retreat ExploreTrails, Botanic Gardens, Kayak and MORE East Boothbay - Kitchen - Washing machine - Dryer - Free Wi-Fi 9.8 Exceptional 32 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=76035591&PinnedHotelID=76035591&HadPinnedHotel=true®ionId=-1&adults=2) ![Marina](https://images.trvl-media.com/lodging/49000000/48960000/48955600/48955502/b4665751.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Twin Ponds Waterfront Guest house Boothbay - Kitchen - Washing machine - Dryer - Air-conditioning 10 Exceptional 22 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=48955502&PinnedHotelID=48955502&HadPinnedHotel=true®ionId=-1&adults=2) ![Outdoor dining](https://images.trvl-media.com/lodging/69000000/68100000/68095200/68095116/8d5f1106.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Oceanfront Home in East Boothbay w/ Linekin Bay Views, Decks, WiFi, Washer/Dryer East Boothbay - Ocean view - Kitchen - Washing machine - Dryer 7.6 Good 8 reviews [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=68095116&PinnedHotelID=68095116&HadPinnedHotel=true®ionId=-1&adults=2) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106100000/106093200/106093185/w1024h677x0y46-9033f211.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### WoodlandView Ldg | Porch + Garden | No Hidden Fees Boothbay Harbor - Pool - Hot tub - Free Wi-Fi - Air-conditioning 10 Exceptional 1 review [](https://www.expedia.co.uk/Hotel-Search?startDate=2026-01-28&endDate=2026-01-29&selected=106093185&PinnedHotelID=106093185&HadPinnedHotel=true®ionId=-1&adults=2) ## 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 Pets not allowed ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know This property is managed by a professional host. The provision of housing is linked to their trade, business or profession. 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 If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal. ### Property is also known as c52b86e8-3c4b-41c8-8367-3bcd0318543c ## About the area 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. [Visit our Boothbay Harbor travel guide](https://www.expedia.co.uk/Boothbay-Harbor.dx6057298) [View more Holiday homes in Boothbay Harbor](https://www.expedia.co.uk/Boothbay-Harbor-Private-Holiday-Homes.d6057298-aaPrivateHolidayHomes.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6&zoom=13&markers=icon:https%3A%2F%2Fa.travel-assets.com%2Ftravel-assets-manager%2Feg-maps%2Fproperty.png%7C43.84402%2C-69.62641&channel=expedia-HotelInformation&maptype=roadmap&scale=1&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=9z38ShRKAdN--IxMhweFGJa8w9M=) Boothbay Harbor, ME ### 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 - ‪Harborside 1901 Bar & Grill - ‬15 min walk - ‪Boothbay Lobster Wharf - ‬4 min walk - ‪Red Cup Coffeehouse - ‬17 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? ### How much is parking at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### What time is check-in at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### What time is check-out at Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina!? ### Where is Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Boothbay Harbor from a Unique Perspective: Stay on the Sailboat Windsong at a Full-Service Marina! Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.co.uk/lp/b/content-guidelines) 10 - Excellent 1 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ## Reviews ### 10/10 Excellent #### Andy W. 17 Aug 2025 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. ##### Andy W. Stayed 3 nights in Aug 2025 ## Expedia's Latest Trends ### Hotels > [Timber Ridge Lodge and Waterpark](https://www.expedia.co.uk/Lake-Geneva-Hotels-Timber-Ridge-Lodge-And-Waterpark.h1043867.Hotel-Information) > > [Hyatt Regency Santa Clara](https://www.expedia.co.uk/Santa-Clara-Hotels-Hyatt-Regency-Santa-Clara.h4313.Hotel-Information) > > [Wuksachi Lodge](https://www.expedia.co.uk/Sequoia-National-Park-Hotels-Wuksachi-Lodge.h893730.Hotel-Information) > > [Dutch Wonderland Inn](https://www.expedia.co.uk/Lancaster-Hotels-Cartoon-Network-Hotel.h50407269.Hotel-Information) > > [Bayshore Resort](https://www.expedia.co.uk/Traverse-City-Hotels-Bayshore-Resort.h34264.Hotel-Information) > > [Fairmont Orchid](https://www.expedia.co.uk/Kamuela-Hotels-Fairmont-Orchid.h25190.Hotel-Information) > > [Aspen Select](https://www.expedia.co.uk/Rochester-Hotels-Aspen-Select.h12245240.Hotel-Information) > > [Maui Coast Hotel](https://www.expedia.co.uk/Kihei-Hotels-Maui-Coast-Hotel.h28645.Hotel-Information) > > [Travelodge by Wyndham Winchester](https://www.expedia.co.uk/Winchester-Hotels-Travelodge-By-Wyndham-Winchester.h9600.Hotel-Information) > > [La Quinta Inn & Suites by Wyndham Myrtle Beach - N Kings Hwy](https://www.expedia.co.uk/Myrtle-Beach-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Myrtle-Beach-N-Kings-Hwy.h6849.Hotel-Information) > > [Sea Crest Beach Resort](https://www.expedia.co.uk/North-Falmouth-Hotels-Sea-Crest-Beach-Hotel.h25567.Hotel-Information) > > [The View Hotel](https://www.expedia.co.uk/Kayenta-Hotels-The-View-Hotel.h59418009.Hotel-Information) > > [Isla Bella Beach Resort & Spa](https://www.expedia.co.uk/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information) > > [Anvil Hotel](https://www.expedia.co.uk/Jackson-Hole-Hotels-Anvil-Hotel.h894210.Hotel-Information) > > [Yosemite View Lodge](https://www.expedia.co.uk/El-Portal-Hotels-Yosemite-View-Lodge.h576660.Hotel-Information) > > [La Quinta Inn & Suites by Wyndham Cocoa Beach Oceanfront](https://www.expedia.co.uk/Cocoa-Beach-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Cocoa-Beach-Oceanfront.h894002.Hotel-Information) > > [Holiday Inn Express & Suites Price by IHG](https://www.expedia.co.uk/Price-Hotels-Holiday-Inn-Express-Suites-Price.h9253345.Hotel-Information) > > [Holiday Inn Key Largo by IHG](https://www.expedia.co.uk/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) > > [Baymont by Wyndham Mishawaka South Bend Area](https://www.expedia.co.uk/South-Bend-Hotels-Baymont-By-Wyndham-Mishawaka-South-Bend-Area.h1976.Hotel-Information) > > [Solterra Resort](https://www.expedia.co.uk/Orlando-Hotels-Solterra-Resort.h18526478.Hotel-Information) > > [Comfort Inn & Suites Napoleon](https://www.expedia.co.uk/Defiance-Hotels-Comfort-Inn-Suites.h200743.Hotel-Information) > > [Bar N Ranch](https://www.expedia.co.uk/West-Yellowstone-Hotels-Bar-N-Ranch.h11548135.Hotel-Information) > > [Holiday Inn Resort Bar Harbor - Acadia Natl Park by IHG](https://www.expedia.co.uk/Bar-Harbor-Hotels-Holiday-Inn-Resort-Bar-Harbor-Acadia-Natl-Park.h26045.Hotel-Information) > > [Yosemite Southgate Hotel & Suites](https://www.expedia.co.uk/Oakhurst-Hotels-Yosemite-Southgate-Hotel-Suites.h3650.Hotel-Information) > > [Nonantum Resort](https://www.expedia.co.uk/Portland-Hotels-Nonantum-Resort.h2936780.Hotel-Information) > > [Gurney's Montauk Resort & Seawater Spa](https://www.expedia.co.uk/Montauk-Hotels-Gurneys-Montauk-Resort-Seawater-Spa.h7033726.Hotel-Information) > > [Hotel Marguerite Anaheim/Garden Grove, Trademark Collection by Wyndham](https://www.expedia.co.uk/Garden-Grove-Hotels-Holiday-Inn-Express-Suites-Garden-Grove-Anaheim-South.h917954.Hotel-Information) > > [Riviera Resort Palm Springs](https://www.expedia.co.uk/Palm-Springs-Hotels-Margaritaville-Resort-Palm-Springs.h26011.Hotel-Information) > > [Balmoral Resort Florida](https://www.expedia.co.uk/Haines-City-Hotels-Balmoral-Resort-Florida.h19447044.Hotel-Information) ---