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Ossining, New York Boat Rentals

Page 1 of 124 listings

Great 30' boat on Hudson River
Powerboats in Ossining · 8 guests

Great 30' boat on Hudson River

5.0
$150-$200hour
21 ft Bayliner Bowrider, Wake board and fishing available.
Powerboats in New York · 9 guests

21 ft Bayliner Bowrider, Wake board and fishing available.

New
$150hour
Luxury 35' Private Yacht - NYC Best Experience
Events in New York · 6 guests

Luxury 35' Private Yacht - NYC Best Experience

New
$400hour
Enjoy Spacious Sailing with our Large Catamaran on the Beautiful Hudson River!
Sailing in New York · 12 guests

Enjoy Spacious Sailing with our Large Catamaran on the Beautiful Hudson River!

5.0
$624-$750hour
Boston Whaler 230 Outrage - Enjoy some time on the Long Island Sound
Powerboats in Greenwich · 6 guests

Boston Whaler 230 Outrage - Enjoy some time on the Long Island Sound

5.0
$130-$175hour
Affordable way to get on the water for a great day!
Powerboats in New York · 6 guests

Affordable way to get on the water for a great day!

New
$200hour
Intimate Motor Yacht Cruising on the Hudson River / New York City!
Events in New York · 6 guests

Intimate Motor Yacht Cruising on the Hudson River / New York City!

New
$550-$750hour
Charter 38' Pearson Cruising Monohull In Mamaroneck, New York
Sailing in Mamaroneck · 10 guests

Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

5.0
$100person
Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!
Sailing in Bronx · 6 guests

Sunset C&C Sailboat cruise outside of NYC: the beauty of Long Island!

New
$95person
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$95person
Fun in the Sun with Manhattan skyline in the background
Sailing in Bronx · 6 guests

Fun in the Sun with Manhattan skyline in the background

New
$95person
Enjoy a day trip, NYC sightseeing, or an evening dinner cruise!
Events in Stamford · 6 guests

Enjoy a day trip, NYC sightseeing, or an evening dinner cruise!

New
$250-$450hour
Custom Boating Adventure in Stamford, Connecticut.
Powerboats in Stamford · 5 guests

Custom Boating Adventure in Stamford, Connecticut.

5.0
$125hour
27ft 2022 Pontoon w/ Slide - 11 people
Powerboats in Stamford · 11 guests

27ft 2022 Pontoon w/ Slide - 11 people

New
$175hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300hour
Sailing JOURNEY on the Sound
Sailing in Stamford · 6 guests

Sailing JOURNEY on the Sound

New
$262hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Sailing in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

5.0
Superowner
$37person
27' Cierra Bayliner Yacht for Daily Charter in New York
Powerboats in Bronx · 8 guests

27' Cierra Bayliner Yacht for Daily Charter in New York

New
$300hour
Port Washington Private Yacht Charter - 52' Okean Flybridge
Events in Port Washington · 12 guests

Port Washington Private Yacht Charter - 52' Okean Flybridge

5.0
$700hour
Port Washington Private Yacht Charter - 43' Azimut Flybridge
Events in Port Washington · 12 guests

Port Washington Private Yacht Charter - 43' Azimut Flybridge

5.0
$334-$400hour
 Welcome aboard embark on our 38ft charter relax, and enjoy Sunsets Cruises
Events in Norwalk · 6 guests

Welcome aboard embark on our 38ft charter relax, and enjoy Sunsets Cruises

5.0
$285-$350hour
Robalo 207 Center Console for Rent in Norwalk
Powerboats in Norwalk · 6 guests

Robalo 207 Center Console for Rent in Norwalk

5.0
$150hour
Sail from Norwalk, CT - $220/Hour - $37/Person
Sailing in Norwalk · 10 guests

Sail from Norwalk, CT - $220/Hour - $37/Person

4.6
Superowner
Best of 2023
$36person
 Welcome aboard embark on our 33ft charter relax, and enjoy Sunsets Cruises
Events in Norwalk · 6 guests

Welcome aboard embark on our 33ft charter relax, and enjoy Sunsets Cruises

New
$265-$300hour

Ossining Reviews

  1. Lisa

    Lisa

    Charter 38' Pearson Cruising Monohull In Mamaroneck, New York

    Rick you made our first wedding anniversary so special. Thank you for your suggestion to dine and dock, your knowledge on the history of the area and for your great sense of humor! We had a great time! Nirvana is such a beautiful vessle

  2. BL

    Brenda

    Custom Boating Adventure in Stamford, Connecticut.

    We had a beautiful sunset cruise with Alex on from Harbor Point Marina in Stamford. His directions to park and meet at the marina were spot on. The boat was clean and comfortable- perfect for 4 of us passengers. It was super calm water, so we were able to go to go to Greenwich Harbor as well. We will be back! Thank you for a great boat trip.

  3. JT

    John

    Welcome aboard embark on our 38ft charter relax, and enjoy Sunsets Cruises

    Captain Mitch was great, we had a great day on the water for my wife’s birthday. Would recommend to anyone looking for a relaxing day out.

  4. AM

    Amy

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco was a perfect, he was knowledgeable and accommodating. The trip was enjoyable and relaxing. Highly recommend.

  5. Deasha

    Deasha

  6. RL

    Roy

    Great 30' boat on Hudson River

    I’ve been going out on charters for years and I must say that Captain Les knows how to bring out the best in people! It takes great skill for a certified captain, to make you feel safe at the same time, relax and unwind, or party it up and create the atmosphere you want! It feels like Les can be your best friend and join your conversation, or he lays back and gives you all the space you want. He knows the Hudson River like the back of his hand and his boat is well maintained and very clean and comfortable! He played some of our favorite music on a great sound system! Later we wanted peace and quiet as we cruised up the Hudson with a beautiful backdrop of the bear mountains. We pulled up and docked in Coldspring and had a great lunch in town. I have already booked my next trip with him and am thinking of planning a birthday party for the fall. 5 out of 5 stars!