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Chilmark, Massachusetts Boat Rentals

60' Cruising Monohull Ketch in Vineyard Haven, MA
Sailing in Tisbury · 12 guests

60' Cruising Monohull Ketch in Vineyard Haven, MA

5.0
$200-$275hour
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
Snoozed - Active 03 Nov 2024
Sunset Sail Buzzards Bay in a Classic Sloop!
Sailing in Fairhaven · 4 guests

Sunset Sail Buzzards Bay in a Classic Sloop!

New
$150hour
31ft Contender Center Console - Fishing Charter
Fishing in Westport · 6 guests

31ft Contender Center Console - Fishing Charter

5.0
$110hour
Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat
Sailing in Mattapoisett · 6 guests

Spend the Day on Buzzards Bay - Sail on a J/105 or Cruise on a Dyer 29 Powerboat

New
$70person
28ft Whitewater Center Console Rental in Mashpee, Massachusetts
Powerboats in Mashpee · 6 guests

28ft Whitewater Center Console Rental in Mashpee, Massachusetts

5.0
$300hour
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
$399hour
8 Person Center Console Rental in Osterville Massachusetts
Powerboats in Barnstable · 8 guests

8 Person Center Console Rental in Osterville Massachusetts

5.0
$275hour
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
$350hour
Yamaha 195S Wakeboat in Sandwich
Powerboats in Sandwich · 8 guests

Yamaha 195S Wakeboat in Sandwich

5.0
$750day
Cruise Martha's Vineyard and Cape Cod on a Captained 30ft Back Cove
Powerboats in Wareham · 6 guests

Cruise Martha's Vineyard and Cape Cod on a Captained 30ft Back Cove

New
Snoozed - Active 17 May 2024
Cobia 35' Charter tours in Newport on a 2021 Power Yacht
Powerboats in Newport · 6 guests

Cobia 35' Charter tours in Newport on a 2021 Power Yacht

New
$700hour
PRIVATE and SAFE Newport Harbor Tour, Picnic and Swim
Powerboats in Newport · 6 guests

PRIVATE and SAFE Newport Harbor Tour, Picnic and Swim

5.0
$200hour
Pro 24' RIB rental in Barrington
Powerboats in Newport · 6 guests

Pro 24' RIB rental in Barrington

5.0
$600day
41' Catana Cruising Catamaran for Charter in Newport, RI
Sailing in Newport · 6 guests

41' Catana Cruising Catamaran for Charter in Newport, RI

5.0
$290hour
Private Sailing Charter Newport, Bristol RI | Captain and Crew
Sailing in Newport · 6 guests

Private Sailing Charter Newport, Bristol RI | Captain and Crew

New
$120-$175hour
Instant Book
36' Classic Powerboat Rental In Newport, Rhode Island
Powerboats in Newport · 28 guests

36' Classic Powerboat Rental In Newport, Rhode Island

5.0
$470hour
Oldport 26 Yacht Club Launch for charter in Newport RI
Powerboats in Newport · 14 guests

Oldport 26 Yacht Club Launch for charter in Newport RI

5.0
$285hour
26' Brownell Powerboat for 14 people in Newport
Powerboats in Newport · 14 guests

26' Brownell Powerboat for 14 people in Newport

4.9
$285hour
Griffin Yachts RIB GY 390 in Newport
Powerboats in Newport · 6 guests

Griffin Yachts RIB GY 390 in Newport

5.0
$125hour
MOOSE- 35ft Downeaster. Bachelorettes, Sunset Tours & more!
Powerboats in Newport · 6 guests

MOOSE- 35ft Downeaster. Bachelorettes, Sunset Tours & more!

5.0
$355hour
Charters Newport Rhode Island
Powerboats in Newport · 6 guests

Charters Newport Rhode Island

New
$250hour
Fun, Sun & Fast Best Luxury Day Yacht Newport
Events in Newport · 10 guests

Fun, Sun & Fast Best Luxury Day Yacht Newport

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

Custom Sailing Charter - Newport/ Block Island

5.0
$290hour

Top Destinations Nearby

Chilmark Reviews

  1. SD

    Stewart

    60' Cruising Monohull Ketch in Vineyard Haven, MA

    Sequoia and his crew were very accommodating. My wife had been in an accident and was wearing a cast. They made sure they used the utmost care in getting her on and off the boat. The weather was beautiful and we toured the harbor and they gave us a history of some of the tall ships and wooden boat yard. The recommendation for lunch at the Black Dog was great. Fun time _/)

  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. jg

    janet

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

    christian was easy to communicate with and super responsive to a list of questions and weather concerns. he was patient and professional. couldn't have asked for a better day on the water. on time. gorgeous boat. superb crew. so thrilled to be their first GMB clients. went to vineyard for lunch, anchored, swam and cruised. HIGHLY recommend! we will be back for sure.

  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.