Cookies & Agreements

By continuing to use this website, you have read and agree to the Terms of Use and agree to the collection and use of your information by cookies and similar technologies, as set forth in our Privacy Policy.

Getmyboat Logo
    All listings in Massachusetts

    Incredible sailboat rentals in Massachusetts, United States.

    5.0
    (245 Reviews)

    Page 2 of 2 • 28 listings

    • Recommended
    • Price: Low to High
    • Price: High to low
    • Highest Rated
    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston
    Sailing in Boston · 8 guests

    Luxury Charter on Peningo - 50' World Class Sailing Racer/Cruiser in Boston

    New
    $550/hour
    Instant Book
    Able Custom 42' Chartered Sailing Experience in Stonington, CT
    Sailing in Stonington · 3 guests

    Able Custom 42' Chartered Sailing Experience in Stonington, CT

    New
    $200+/hour
    Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!
    Sailing in Gloucester · 60 guests

    Authentic 122ft Tall Ship Schooner Adventure - A National Historic Landmark!

    New
    $1,200+/hour
    Private Sailing Charter on Martha's Vineyard
    Sailing in Tisbury · 6 guests

    Private Sailing Charter on Martha's Vineyard

    5.0
    Snoozed - Active 02 Jul 2026

    Top Destinations Nearby

    Sailing Reviews in Massachusetts

    1. MR

      MV Landmarks

      Private Sailing Charter on Martha's Vineyard

      We really enjoyed sailing on the Miss Marilyn in Vineyard Sound. The sail was amazing and the captain was so knowledgeable and engaging. We most highly recommend the experience!

    About

    1. About Getmyboat
    2. Careers
    3. Media Inquiries
    4. Terms of Use
    5. Privacy Policy
    6. Cookies Policy
    7. Accessibility Statement
    8. Member Interface Agreement
    9. Sitemap
    10. Contact Us

    Learn More

    1. How It Works
    2. For Owners
    3. Mobile Apps
    4. Safety

    Experiences

    1. Boat Rentals
    2. Jet Ski Rental
    3. Fishing Charters
    4. Houseboat Rental
    5. Pontoon Rental
    6. Yacht Rental
    7. Sailboat Rental
    8. Bachelorette Party Boat Rental
    9. Party Boat Rentals

    Journal

    1. Company News
    2. Lifestyle
    3. Experiences Guide
    4. Destinations
    5. Tips for Renters and Owners

    Popular Destinations

    1. Miami
    2. Lake Lanier
    3. Lake Tahoe
    4. San Diego
    5. Lake Travis
    6. Newport Beach
    7. Chicago
    8. Lake Norman
    9. Key Largo
    10. Destin
    11. Marathon

    24/7 Live Support

    1. Help & FAQs
    2. +1 818 927 2148
    3. support@getmyboat.com

    Real reviews from happy Getmyboaters.

    4.9 out of 5! 500,000+ reviews

    • Download on the App Store
    • Get it on Google Play
    © Getmyboat 2026
    TermsPrivacy