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The Best Sailboat Rentals Near Ossining

Browse, book, and get out onto the water with local captains and boat owners.

Our Favorite Sailboat Rentals Near Ossining

4.9 (4,839 reviews)

•

Sailing in Ossining · 6 guests
Sailboat on the Hudson
New
$150/hour
Sailing in New York · 12 guests
Enjoy Spacious Sailing with our Large Catamaran on the Beautiful Hudson River!
5.0
$624+/hour
Sailing in Mamaroneck · 10 guests
Charter 38' Pearson Cruising Monohull in Mamaroneck, New York
5.0
$50/hour
Tours in Bronx · 6 guests
ASA practice sailing exercizes
New
$150/hour
Sailing in Bronx · 6 guests
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
New
$150/hour
Sailing in Bronx · 6 guests
Fun in the Sun with Manhattan skyline in the background
New
$150/hour
Sailing in Stamford · 6 guests
Sailing JOURNEY on the Sound
New
$262/hour
Tours in Stamford · 6 guests
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
4.9
Superowner
$180+/hour
Sailing in Norwalk · 12 guests
Sail from Norwalk/Westport, CT - $200/Hour - $33.33/Person
4.7
Superowner
Best of 2023
$200/hour
Sailing in Port Washington · 6 guests
Sailing Long Island Sound with Captain Steve
5.0
$199/hour
Sailing in Port Washington · 6 guests
Sail From Port Washington, NY - $219/Hour - $37/Person
4.8
Superowner
Best of 2023
$219/hour
Sailing in Oyster Bay · 6 guests
Sail Long Island's Gold Coast on this beautiful 36' Jeanneau!
5.0
$185+/hour

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Suggested Searches

This weekend $100-$300 trips 2-4 people Captained

Types of Boats Popular in Ossining

Top Sailboat Rental Locations Near Ossining

Most Popular Yacht Rentals in Ossining

Events in Queens · 12 guests
"The Betty" Pacemaker Motor Yacht
New
$594/hour
Events in Manhattan · 8 guests
SEA RAY 450 SUNDANCER 47 ft
5.0
$650/hour
Events in Manhattan · 35 guests
60ft Hatteras Luxury Motor Yacht in NY Harbor - USCG Inspected
5.0
$1,100/hour
Events in Manhattan · 300 guests
130ft Luxury Yacht Private Charter in NYC | 6-Course Dinner and Live Music
New
$8,000/hour

Most Popular Boat Tours in Ossining

Powerboats in Brooklyn · 6 guests
Jeanneau Leader 9.0 CC for rent in Brooklyn
5.0
$251+/hour
Events in Brooklyn · 12 guests
New Luxury Yacht w/Fly-Bridge, Sunpads, Fits 12 People Pickup Brooklyn/ Nyc / NJ
5.0
$895/hour
Events in Manhattan · 12 guests
Grady White Freedom 40' Yatch! 12 people
5.0
$500/hour
Sailing in Manhattan · 6 guests
North River Sailing - See NYC from a Classic Racing Yacht
5.0
$275/hour

Most Popular Pontoon Rentals in Ossining

Powerboats in Queens · 15 guests
15 Passenger 28ft Comfortable Starcraft Pontoon Boat
New
$305+/hour
Powerboats in Queens · 10 guests
10 Passenger Comfortable Pontoon Boat - for fun with families / friends
5.0
$160+/hour
Powerboats in Manhattan · 26 guests
35ft Cycleboat Party Boat Rental in Manhattan
5.0
$499/hour
Powerboats in Queens · 6 guests
6 Passenger Pontoon Suntracker 18 DLX
5.0
$274+/hour

Recent Reviews in Ossining

Top Sailboat Rental Locations in the United States

How To Book on Getmyboat

4.9 out of 5! • 500,000+ reviews

Browse
Find the right listing for you and your crew, with options for boat types, group size, captained or self-charter, and lots more.
Inquire & Book
Found one you like? Send a rental inquiry with your preferred trip details, and you’ll receive an offer from your captain to book.
Enjoy
Coordinate a pick-up place and time, meet your boat captain, and get out onto the water!

Real reviews from happy Getmyboaters.

4.9 out of 5! 500,000+ reviews

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