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Browse Massachusetts Boat Rentals.

Page 1 of 112 listings

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat
Sailing in Tisbury · 6 guests

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

5.0
Superowner
$250/hour
Instant Book
Ocean Oasis: Newport's 51ft Party Yacht for Unforgettable Coastal Soirées!
Events in Newport · 20 guests

Ocean Oasis: Newport's 51ft Party Yacht for Unforgettable Coastal Soirées!

5.0
$500/hour
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27' Blackfin Center Console in Osterville & Barnstable, Cape Cod
Powerboats in Barnstable · 6 guests

27' Blackfin Center Console in Osterville & Barnstable, Cape Cod

5.0
$350/hour
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Custom Sailing Charter - Newport/ Block Island
Sailing in Newport · 6 guests

Custom Sailing Charter - Newport/ Block Island

5.0
$290/hour
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Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht
Powerboats in Fall River · 10 guests

Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht

5.0
$300/hour
Instant Book
90min BYOB Cycleboat Boston Private Charter in Boston Harbor up to 16pp Mon-Thu
Events in Boston · 16 guests

90min BYOB Cycleboat Boston Private Charter in Boston Harbor up to 16pp Mon-Thu

5.0
$395/hour
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38' Power downeast cruiser yacht in Hull or  Boston
Events in Boston · 6 guests

38' Power downeast cruiser yacht in Hull or Boston

5.0
$225/hour
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Come onboard the 45ft Tiara Sovran Motor Yacht
Powerboats in Fairhaven · 10 guests

Come onboard the 45ft Tiara Sovran Motor Yacht

5.0
$399/hour
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20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar
Powerboats in Connecticut · 7 guests

20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar

5.0
$140/hour
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Overspray in Old Saybrook | 37ft Silverton Yacht
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook | 37ft Silverton Yacht

5.0
$300/hour
Instant Book
Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts
Sailing in Salem · 6 guests

Private Charters on Classic 80' Sailing Schooner in Salem, Massachusetts

5.0
$550/hour
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The Best Boston Fun Cruise Aboard 49ft Motor Yacht
Events in Boston · 35 guests

The Best Boston Fun Cruise Aboard 49ft Motor Yacht

New
$700+/hour
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Massachusetts Reviews

  1. Rodney

    Rodney

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    Highly recommend if you’re looking for something different to do than what all the other tourists are doing when visiting Martha’s Vineyard, you might want to consider contacting Mason for a peaceful & relaxing sailboat ride to see the beautiful coastline of MV that most don’t get to experience while on land. We’ll definitely be back next year to do another trip

  2. NA

    Nicholas

    38' Power downeast cruiser yacht in Hull or Boston

    Captain Paul was all around amazing! From the moment we booked our trip, the Captain communicated with us every step of the way. He even called us to let us know the weather forecast for our trip as there was a possibility for potential rough seas. He alleviated any concerns that we had,as we are not active boaters. If you are looking to book a trip, you absolutely can not go wrong with Captain Paul. He actually cares about your experience. You would be hard pressed to find a friendlier, more knowledgeable and experienced Captain. 5 stars

  3. JK

    Jacqui

    Spend a day of sun and fun aboard our 42’ Silverton Motor Yacht

    We booked this boat for my bachelorette trip, and it could not have been more perfect! From the moment we stepped onboard, everything was clean, spacious, and exactly as advertised. The captain was friendly, professional, and made sure we had the best experience—he even knew all the best spots for swimming, cruising, etc. The boat had plenty of room for our group to relax, dance, and enjoy the sunshine. The sound system was amazing (a must for a bachelorette party!), and there was a cooler/fridge ready for our drinks and snacks. We loved that we could customize our day—whether we wanted to anchor and swim, explore the area, or just cruise around with music and laughter. It was the highlight of our trip, and every single person in our group said they’d do it again in a heartbeat. If you’re looking for the perfect mix of fun, relaxation, and gorgeous views, this is 100% the way to go. Highly recommend for any bachelorette or special celebration!

  4. Georgia

    Georgia

    Ocean Oasis: Newport's 51ft Party Yacht for Unforgettable Coastal Soirées!

    We had absolutely incredible time!!! We brought pizza and drinks (which were easy to keep cool because of the icebox on board), got to see some of the famous mansions, went swimming in the cove, and got amazing sunset pictures.

  5. GE

    Gerald

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    By far the best part of our trip to Martha’s Vineyard and the highlight of my girlfriend’s birthday was our time on Captain Mason and Captain Lynne’s boat. They thought of every detail, including birthday decorations and helping me with multiple surprises, took us to the most beautiful spots along the coast and harbor, and even let us partake in a super unique light show boat parade experience. This is by far the best value for money and most unique and relaxing / beautiful experience you could have in the Vineyard. Please trust me and book! Mason and Lynne are also wonderful people who really try to make your experience as amazing as possible. Thank you so much for everything!!!

  6. JK

    John

    Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

    I don’t usually write detailed reviews, but this experience definitely deserves a shoutout. Capt. Mason and Capt. Lynne were incredibly responsive from the moment I submitted the reservation request. I was planning to propose to my girlfriend of 10 years during the sail, and they went above and beyond to help make it perfect. We now have an extremely loved memory that we will cherish for our whole life. Even when I had to make some last minute changes, they were super flexible and understanding. To anyone reading this—if you’re looking for an unforgettable experience with your loved one, this is it. Book it!