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Browse & Book Boat Rentals in Martha's Vineyard, MA.

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

Martha’s Vineyard Private Sailing onboard 42ft Pearson Sailboat

New
$125/hour
Sea Ray 280 Motor Yacht Rental in Oak Bluffs, Massachusetts
Events in Oak Bluffs · 6 guests

Sea Ray 280 Motor Yacht Rental in Oak Bluffs, Massachusetts

New
$550/hour
28ft Whitewater Center Console Rental in Mashpee, Massachusetts
Powerboats in Mashpee · 6 guests

28ft Whitewater Center Console Rental in Mashpee, Massachusetts

5.0
$300/hour
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

5.0
$150/hour
Spend the Day on Buzzards Bay - Sail on "Hamlet" a 35 '  J/105 racer/cruiser
Sailing in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Sail on "Hamlet" a 35 ' J/105 racer/cruiser

5.0
Snoozed - Active 17 May 2025
Spend the Day on Buzzards Bay - Aboard the classic Dyer 29 Classic Boat
Tours in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Aboard the classic Dyer 29 Classic Boat

5.0
Snoozed - Active 17 May 2025
Sail Away on Our Passion: Your 42-Foot Pearson for a Day or Weekend Adventure
Sailing in Dartmouth · 6 guests

Sail Away on Our Passion: Your 42-Foot Pearson for a Day or Weekend Adventure

New
$150/hour
Instant Book
8 Person Center Console Rental in Osterville Massachusetts
Powerboats in Barnstable · 8 guests

8 Person Center Console Rental in Osterville Massachusetts

5.0
$275/hour
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
39' Yellowfin with Quad Engines, Fast & Fun, Cape Cod & the Islands
Powerboats in Barnstable · 10 guests

39' Yellowfin with Quad Engines, Fast & Fun, Cape Cod & the Islands

New
$1,000/hour
Come onboard the 45ft Tiara Sovran Motor Yacht Charter Keep'N It Reel
Powerboats in Fairhaven · 10 guests

Come onboard the 45ft Tiara Sovran Motor Yacht Charter Keep'N It Reel

5.0
$399/hour
Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht
Sailing in New Bedford · 6 guests

Come Sail & Party on Maybellene our well cared for 34' Beneteau Yacht

5.0
$150/hour
Yamaha 195S Wakeboat in Sandwich
Powerboats in Sandwich · 8 guests

Yamaha 195S Wakeboat in Sandwich

5.0
Snoozed - Active 29 Aug 2025
Cape Cod Canal Charters and beyond on your private boat!
Powerboats in Bourne · 6 guests

Cape Cod Canal Charters and beyond on your private boat!

New
$325+/hour
31ft Contender Center Console - Fishing Charter
Fishing in Westport · 6 guests

31ft Contender Center Console - Fishing Charter

5.0
$110/hour
Cruise Martha's Vineyard, Cuttyhunk and Cape Cod Canal
Powerboats in Wareham · 6 guests

Cruise Martha's Vineyard, Cuttyhunk and Cape Cod Canal

New
$298/hour
Half Day 26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod
Powerboats in Barnstable · 12 guests

Half Day 26’ Regulator Center Console Powerboat Rental in Hyannis Harbor Cape Cod

New
$250/hour
Full Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

Full Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690/day
Half Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 8 guests

Half Day Rental | 18′ Outrage Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$119/hour
Half Day Rental | 17′ Montauk Center Console Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Half Day Rental | 17′ Montauk Center Console Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$99/hour
Half Day Rental | 16ft Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 6 guests

Half Day Rental | 16ft Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$99/hour
Full Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Full Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$690/day
Half Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 7 guests

Half Day Rental | 18′ Ventura Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

5.0
$119/hour
Full Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod
Powerboats in Barnstable · 9 guests

Full Day Rental | 20' Dauntless Boston Whaler in Hyannis Harbor, Massachusetts - Cape Cod

New
$775/day

Martha's Vineyard Reviews

  1. TI

    Tony

    Sunset Sail Buzzards Bay in a Classic Sloop!

    I recently had the pleasure of sailing with Captain Freddie on his boat for a surprise two-hour cruise with my girlfriend, and it was an unforgettable experience. From the moment we stepped aboard, we were treated to breathtaking views of Buzzard's Bay and a sense of tranquility that only the open water can offer. The scenic beauty of the surroundings was truly stunning, and we found ourselves captivated by the serene atmosphere that only a sailboat can provide. Freddie was an absolute delight and contributed significantly to the enjoyment of our trip. His friendly and attentive personality put us at ease, and his passion for sailing was evident throughout the journey. He told us all about his restoration of his boat and made sure we were comfortable and well taken care of. We knew nothing about sailing, and he explained all about how the sails work, answered my endless questions, and his expertise and seamanship were evident. We felt completely safe under his guidance. The overall experience was nothing short of magical. From the sunshine and fresh air to laughing and relaxing on the deck while Freddie told us all about the area and his tales of trips to Martha's Vineyard and beyond. I scored some serious romance points with my lady by booking this trip. I would 100% sail with Captain Freddie again without hesitation.

  2. Barbara

    Barbara

    28ft Whitewater Center Console Rental in Mashpee, Massachusetts

    We were very impressed with Capt Mike! His communication was impeccable! Incredibly responsive! His boat was very clean! He was very kind and understanding. He took us on a lovely tour out of Mashpee! We couldn't have asked for a better experience. Would HIGHLY recommend hiring Capt Mike for your charter. Seriously an amazing afternoon.

  3. PO

    Patricia

    8 Person Center Console Rental in Osterville Massachusetts

    Bill was the best captain. He was attentive and wanted to make sure everyone was happy and doing what they wanted. We had a mixed age group but they all enjoyed it. Seeing MV from the water and relaxing on the beach in Chappy was a highlight! We definitely recommend Bill!

  4. KN

    Kelley

    8 Person Center Console Rental in Osterville Massachusetts

    We had such a fun time with Captain Bill! This was the perfect outing for our group of 7. Captain Bill had great music and a very clean boat. Awesome time overall. We would recommend Captain Bill to anyone looking to have a fantastic day on the water.

  5. Web

    Web

    8 Person Center Console Rental in Osterville Massachusetts

    Bill was very gracious and accommodating. He shared his knowledge and enthusiasm for the water with our young children and us equally well. We had an amazing afternoon that included catching fish and seeing some beautiful and secluded spots - in both Cape Cod and Martha’s Vineyard.

  6. Ryan

    Ryan

    8 Person Center Console Rental in Osterville Massachusetts

    2d time with Captain William and once again, he did not disappoint. Took 6 kids with us and we had a blast tubing and fishing. We all left with huge smiles on our faces and lifelong memories. William was a true pro, accommodating, and a fabulous tour guide.