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Sleepy Hollow, New York Boat Rentals

Hudson River excursions to West Point, the Statue, Citi Field & local landmarks
Powerboats in Tarrytown · 6 guests

Hudson River excursions to West Point, the Statue, Citi Field & local landmarks

5.0
$498/hour
Great 30' boat on Hudson River
Powerboats in Ossining · 8 guests

Great 30' boat on Hudson River

5.0
$150+/hour
Sailboat on the Hudson
Sailing in Ossining · 6 guests

Sailboat on the Hudson

New
$150/hour
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+/hour
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!

5.0
$230/hour
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+/hour
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
$50/hour
"Roger That" Yacht Charter in NY
Events in Mamaroneck · 6 guests

"Roger That" Yacht Charter in NY

New
$599/hour
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+/hour
ASA practice sailing exercizes
Tours in Bronx · 6 guests

ASA practice sailing exercizes

New
$150/hour
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
$150/hour
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
$150/hour
Enjoy a day trip, NYC sightseeing, or an evening dinner cruise!
Events in Greenwich · 6 guests

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

New
$250+/hour
Enjoy the sun, Sunset/Nightfall, or summer night sky, or go for a swim.
Powerboats in Bronx · 7 guests

Enjoy the sun, Sunset/Nightfall, or summer night sky, or go for a swim.

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

Custom Boating Adventure in Stamford, Connecticut.

5.0
$150/hour
Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut
Tours in Stamford · 6 guests

Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

4.9
Superowner
Best of 2025
$180+/hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

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

Sailing JOURNEY on the Sound

New
$262/hour
Port Washington Private Yacht Charter - 43' Azimut Flybridge
Events in Port Washington · 12 guests

Port Washington Private Yacht Charter - 43' Azimut Flybridge

4.8
$360+/hour
Port Washington Private Yacht Charter - 52' Okean Flybridge
Events in Port Washington · 12 guests

Port Washington Private Yacht Charter - 52' Okean Flybridge

5.0
$700/hour
Power in Edgewater bayliner
Powerboats in Manhattan · 6 guests

Power in Edgewater bayliner

New
$250/hour
Private Yacht charter for all occasions in NY/NJ
Events in Manhattan · 6 guests

Private Yacht charter for all occasions in NY/NJ

5.0
Superowner
$299/hour
42' Sedan Bridge Carver Santego Motor Yacht Charter in Edgewater, NJ
Events in Manhattan · 6 guests

42' Sedan Bridge Carver Santego Motor Yacht Charter in Edgewater, NJ

5.0
$400/hour
46' Silverton Motor Yacht Charters in Port Washington, New York
Events in Port Washington · 6 guests

46' Silverton Motor Yacht Charters in Port Washington, New York

New
$538/hour

Sleepy Hollow Reviews

  1. Tara

    Tara

    Hudson River excursions to West Point, the Statue, Citi Field & local landmarks

    I reached out to book this boat around 10am and connected with Capt Glenn who was the owner of the boat. After easy communication, I was on the boat with my 3 children at 1pm (3 hours later!) with Capt Brian and his first mate, Serena. They were both very kind and easy to be around. We just wanted a lazy day on the water that that is exactly what they gave us. The boat was clean and everything we had hoped for. Without hesitation, I highly recommended Glenn, his boat and his staff. Thank you, Glenn, Brian and Serena for an awesome afternoon.

  2. 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!

  3. JG

    Jackie

    Great 30' boat on Hudson River

    LES AND JASON WERE AMAZING! They both made my family feel safe, they were so fun and kind! Great customer service! If i could give them a 10 star rating, I would. I’ve rented so many boats in many states and I have to say Les was the best! I recommend him 100000% to anyone wanting to rent a boat for any event. I rented this for my cousin’s birthday and Les and Jason made her feel super special! The boat was better than the pictures, clean very comfy and big for a party of 7! The sound system was awesome and they provided ice for our drinks ;) Thank you both! We had a great time…..we will definitely see you on our next boat rental.

  4. CN

    Chenese

    Great 30' boat on Hudson River

    Les was such a great host! I chartered his boat to take a few girlfriends out for the day. Hearing it was their first time out, Les recommended a laid back itinerary for us. He ensured all of our needs were met, was extremely flexible and professional. An overall excellent time out on the water and we could not have asked for a more beautiful day. Thank you Les! We will see you again soon!!

  5. AS

    Alondra

    Great 30' boat on Hudson River

    MOST AMAZING EXPERIENCE ON A BOAT EVER! Definitely recommend 100%. We were a group of 9, they were very attentive to us & treated us in a very respectful manner. We had a blast! They allowed us to play our own music, took us to a private place where all boats stand, & gave us some information about the area. Will definitely be booking again! Thank you Les! 😁

  6. DN

    Dennis

    Great 30' boat on Hudson River

    Today's boating trip was terrific! Not only did the weather cooperate, but the captain was very friendly with my family. We felt comfortable on his boat and enjoyed our stop for a dunk in the Hudson River. The boat was just the right size for 3 adults and a 3-year-old. Thanks for a relaxing outing!