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Browse Massachusetts Boat Rentals.

Page 6 of 6142 listings

Relax Aboard The Classic Motor Yacht Gypsy in Southern New England and Florida
Events in Barnstable · 6 guests

Relax Aboard The Classic Motor Yacht Gypsy in Southern New England and Florida

New
$120/hour
Newport Boat Days are the Best Days!
Powerboats in Newport · 6 guests

Newport Boat Days are the Best Days!

New
$250/hour
Beautiful  Like New Rinker Fiesta Vee 31' Cruiser
Powerboats in Gloucester · 6 guests

Beautiful Like New Rinker Fiesta Vee 31' Cruiser

New
$175+/hour
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
Instant Book
23ft Seafox Center Console for Fishing Adventure
Fishing in Wellfleet · 6 guests

23ft Seafox Center Console for Fishing Adventure

New
$200/hour
Charter a 45ft Boat in Gloucester – Perfect for Parties, Tours & Swims
Events in Gloucester · 31 guests

Charter a 45ft Boat in Gloucester – Perfect for Parties, Tours & Swims

New
$400+/hour
18ft Godfrey Sweetwater Pontoon Rental in Wilmington
Powerboats in Wilmington · 10 guests

18ft Godfrey Sweetwater Pontoon Rental in Wilmington

New
$450/day
36ft Sportfisherman Boat Charter in Point Judith, Rhode Island
Powerboats in Narragansett · 6 guests

36ft Sportfisherman Boat Charter in Point Judith, Rhode Island

New
$960/day
Captained or Bareboat 22' Boston Whaler Boat! Get on the water today!
Powerboats in Newport · 6 guests

Captained or Bareboat 22' Boston Whaler Boat! Get on the water today!

New
$200/hour
Cruise or Fish Boston Harbor & it's surrounding area with Boston's Best Captain
Powerboats in Boston · 6 guests

Cruise or Fish Boston Harbor & it's surrounding area with Boston's Best Captain

New
$85+/hour
Zippy 17.5ft Bayliner with Trailer
Powerboats in Massachusetts · 7 guests

Zippy 17.5ft Bayliner with Trailer

New
$75/hour
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
40ft Pursuit Express Motor Yacht in Boston
Events in Boston · 6 guests

40ft Pursuit Express Motor Yacht in Boston

New
$300/hour
Hobie outback 2022 ocean fishing kayak
Adventures in Massachusetts · 1 guest

Hobie outback 2022 ocean fishing kayak

New
$300/day
Providence Boat Tour
Powerboats in Cranston · 5 guests

Providence Boat Tour

New
$150/hour
Wakesurfing, Tubing, Wakeboaring,Waterskiing, Lake Cruises on Lake Lillinonah
Events in New Milford · 6 guests

Wakesurfing, Tubing, Wakeboaring,Waterskiing, Lake Cruises on Lake Lillinonah

New
$260/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
Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin
Sailing in Newport · 6 guests

Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

5.0
Best of 2025
Snoozed - Active 03 Apr 2026
43' Sailboat, Bristol RI & Beyond
Sailing in Bristol · 6 guests

43' Sailboat, Bristol RI & Beyond

5.0
Snoozed - Active 03 May 2026
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
Snoozed - Active 02 Jun 2026
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
Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch
Sailing in Tisbury · 6 guests

Martha's Vineyard Best Sailing Charters on 60' Luxury Ketch

New
Snoozed - Active 03 May 2026

Massachusetts Reviews

  1. cC

    chris

    43' Sailboat, Bristol RI & Beyond

    This was an incredible sail. We had to cancel our initial trip due to very bad storms with 65 knot winds and flooding rains early in the season. We rebooked and had a fabulous, relaxing time. The Capt' is both entertaining and a wealth of information and just makes the entire experience what you would want.....sublime.

  2. BA

    Bridget

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    Our sail with Captain Perrin was an absolute dream. We were lucky enough to have gorgeous weather for our sunset sail and Perrin could not have been more accommodating. Our bachelorette party of five loved his historic tidbits and great vibes. Would definitely book again when back in the area!

  3. AH

    Anne

    43' Sailboat, Bristol RI & Beyond

    Four of us had a great sail with Captain Francis. He struck the right balance between chatting with us and letting us talk amongst ourselves. We wanted to sail by a specific area and he graciously complied. I thought the value for the sailing experience was great. Highly recommend.

  4. MH

    Melissa

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    We had a great trip with Kenny - highly recommend. Very prompt, communicative, and clear in departure directions. We had a great sail with beautiful conditions and Kenny is personable and knowledgeable. Highly recommend for a great time on the water, we’ll definitely go sailing with him again next time!

  5. SC

    Steven

    Sailing in Newport- Catalina 320 Sailboat with Captain Kenneth & Captain Perrin

    This wasn’t just a sail—it was an adventure filled with stories, laughter, and the kind of peaceful moments you only find out on the water. I can’t recommend Kenneth highly enough if you’re looking for a memorable and truly enjoyable sailing experience. Highly recommend! 🚤⛵️

  6. BB

    Bryan

    43' Sailboat, Bristol RI & Beyond

    Table for Two and Captain Francis make for a great sail. We have sailed with him multiple times and will continue to do so yearly for our family sailing vacation. Safety, value, and his knowledge of sailing globally make it a great time and experience we return back to every year. I highly recommend his services.