Boat vacation rentals in Massachusetts

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Top-rated boat rentals in Massachusetts

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Guest favorite

Boat in Boston

4.97 out of 5 average rating, 31 reviews

Patriot: Three Story Vessel

Docked in the heart of downtown Boston, this rare, 45 ft. steel trawler is outfitted with all the comforts of home. With two floors of living space, she's certainly spacious enough for the entire family, offering plenty of room for you to spread out and enjoy time on the water with fantastic views of Boston Harbor. Located just steps away from the New England Aquarium, Quincy Market/Faneuil Hall, the North End, Boston Garden, a public ice skating rink, and countless other things to see and do.

Boat in Boston

4.86 out of 5 average rating, 72 reviews

Floating suite in Boston Harbor

Our small yacht is the perfect way to see Boston. Perfect space for a couple or couple and one child. Please note the yacht stays docked during your stay. Walk to many area attractions. Free Wifi. Come home to the boat after a busy day in the city. Enjoy the peacefulness of being on the water, sip a cocktail on the back deck while watching the sailboats skim the harbor and be rocked to sleep every night. Parking is available for an additional $25 per night and will be invoiced separately.

Superhost

Private room in Tisbury

4.17 out of 5 average rating, 6 reviews

Vineyard Haven Harbor 60’ sailboat 2 Cabins 4 beds

Gently rock yourself to sleep on a big beautiful classic sailing yacht. This listing is two Cabins on Tandemeer, a 1980 sailing ketch, 60' long and 15 feet wide. These are the two forward staterooms. Each stateroom has two large comfortable single beds, with storage space underneath for luggage, fans, an opening ceiling hatch, and a private toilet, sink and shower. The spacious main salon, cockpit and deck areas are also available for lounging and enjoying the view from your yacht on the water

Guest favorite

Boat in Boston

4.95 out of 5 average rating, 138 reviews

2BR Spacious Yacht - Heat & AC - On Freedom Trail

Escape the hustle and bustle of the city and unwind aboard Carpe Diem II, a yacht with 2 comfy queen staterooms for up to 4 adults. Each stateroom has a private bathroom and shower. Unwind on the aft deck with meals and cocktails as the boats sail by on the harbor, or warm up or cool off inside with central A/C and heat. Located in Charlestown Navy Yard, steps to Freedom Trail, North End, and Downtown. Book now and enjoy the unique charm of living on the water in this historic neighborhood.

Superhost

Private room in Nantucket

4.86 out of 5 average rating, 170 reviews

Best Harbor Views-50' sailboat

Swimming off the back of the boat in this warm weather is a great way to cool off and start or end your day. The water is just cool enough to make it interesting and refreshing for the first few minutes! Then breakfast in the cockpit with a good pitcher of just pressed hot coffee, toasted bagels and croissants with jam and maybe some fruit on the side. Then off to shore to explore all Nantucket has to offer...a short launch ride lands you on Straight Wharf, the downtown marina and Main St.

Boat in Boston

4.65 out of 5 average rating, 55 reviews

Boston Harbor Yacht Walk to North End

Really fun way to visit Boston. Please note the yacht can not leave the dock. 2003 Carver Yacht with 2 staterooms each with their own bath. Walking distance to USS Constitution, Bunker Hill and the North End. Wifi available. Enjoy the hustle and bustle of the city by day and return to the Sea Pearl for a relaxing evening on the water. Sip a cocktail while overlooking the Boston skyline. Snuggle in to our very comfy berths and be rocked to sleep at night. Parking may be available.

Superhost

Private room in Vineyard Haven, Martha's Vineyard

4.55 out of 5 average rating, 96 reviews

Vineyard Haven Sailboat, 2 Bed Cabin Port

Port side forward Private cabin, two comfortable single berths, nice linens, private head w/ toilet sink & shower, large classic older 1980 sailboat, 60' feet long with four double cabins (may have other guests in them), gorgeous quiet location in Vineyard Haven Harbor. Large living/dining salon, fully equipped galley (kitchen), nice open cockpit dining area, out at anchor in the harbor, so you take the Vineyard Haven Launch from the dock at the Black Dog Wharf to and from the boat.

Superhost

Condo in Falmouth

InnSeason Resorts HarborWalk

Walk out the door, cross the street and catch the Island Queen ferry to Martha's Vineyard. This resort is directly across from Falmouth Harbor, at the center of it all. Just minutes from the beach, you also have easy access to fishing and boating, and it's only a short walk to shopping, dining and more on bustling Main Street. When it's time to take a break, take your beach bag to the on-site tanning deck and enjoy the lovely harbor views.

Top guest favorite

Boat in Boston

5 out of 5 average rating, 79 reviews

Travelers Choice Best of Bos Green Turtle II Yacht

Come stay aboard the Green Turtle II 45 foot yacht in the historic Navy Yard in Boston Harbor. What a fun way to visit the great city of Boston! It is like taking two vacations in one. Visit the city sights and then come back to the boat and relax and enjoy the peace on the water. Restaurants within walking distance. Parking on pier at $28 per day and garage at end of street. Coffee, tea, sugars, cream, juice, waters provided.

Superhost

Private room in Vineyard Haven, Martha's Vineyard

4.6 out of 5 average rating, 131 reviews

Vineyard Haven Sailboat, 2 Bed Private Cabin Stbd

A cozy two berth private cabin on a classic 1980 ocean going sailboat anchored in beautiful Vineyard Haven Harbor. Tandmeer is a 60' Nautical Development ocean cruising ketch, that has been sailed to and from New England and Haiti in the Caribbean every year since 2014. Your cabin is private with two comfortable bunks, opening hatch, and a private head with toilet sink and shower, in a beautiful location.

Guest favorite

Private room in Boston

4.85 out of 5 average rating, 53 reviews

Rozinante - Queen, Harbor View

At Constitution Marina's Bed & Breakfast Afloat you can enjoy the ambiance, the comfort, the romance of staying ON THE WATER with all the amenities of a modern hotel, at rates as low as you'll find anywhere in Boston! For boats with 2 staterooms, there is an additional fee of $100.00 plus tax/night if the 2nd room is rented. The 2nd room is booked directly through the host.

Superhost