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Sleepy Hollow, New York Boat Rentals

Hudson River Tours: West Point, Statue of Liberty, Sleepy Hollow Lighthouse.
Tours in Tarrytown · 6 guests

Hudson River Tours: West Point, Statue of Liberty, Sleepy Hollow Lighthouse.

5.0
$315+/hour
Instant Book
Great 30' boat on Hudson River
Powerboats in Ossining · 6 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
$120+/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
Chris Craft Launch 28: Affordable Luxury for an Unforgettable Day on the Water!
Powerboats in New York · 6 guests

Chris Craft Launch 28: Affordable Luxury for an Unforgettable Day on the Water!

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
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
Sit Back, Relax and Enjoy on a Formula 260 SS!!!
Powerboats in Bronx · 6 guests

Sit Back, Relax and Enjoy on a Formula 260 SS!!!

New
$175+/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
Cruisers 420 Express Cruiser Rental in Long Island Sound
Events in Greenwich · 6 guests

Cruisers 420 Express Cruiser Rental in Long Island Sound

4.8
$425+/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
Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran
Sailing in Bronx · 12 guests

Sail NYC in Style: Luxury Private Charter Aboard the Sleek NEEL 47 Trimaran

New
$813+/hour
Instant Book
Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console
Powerboats in Stamford · 6 guests

Customized Boating Adventure on the Sound | 25ft Seacraft Pacific Center Console

New
Snoozed - Active 25 Nov 2025
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
$225+/hour
32' Luxurious Yacht Certified Express Cruiser
Events in Stamford · 8 guests

32' Luxurious Yacht Certified Express Cruiser

5.0
$300/hour
24ft Cobia: Center Console Versatility- Captain Optional! 3000+ Charters
Powerboats in Stamford · 8 guests

24ft Cobia: Center Console Versatility- Captain Optional! 3000+ Charters

5.0
$200/hour
30ft 2022 Pontoon w/ Slide- Stamford, CT! Charter Specialists. Over 3000+ Trips
Powerboats in Stamford · 10 guests

30ft 2022 Pontoon w/ Slide- Stamford, CT! Charter Specialists. Over 3000+ Trips

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

Sailing JOURNEY on the Sound

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

Glen Cove Private Yacht Charter - 43' Azimut Flybridge

4.9
$360+/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
$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
62ft Searay, a perfect combination of style and class
Powerboats in Port Washington · 12 guests

62ft Searay, a perfect combination of style and class

5.0
$850+/hour

Sleepy Hollow Reviews

  1. MR

    Madeleine

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Such a fun evening on the water with Marco. A very comfortable boat, easy to access and a beautiful cruise! Highly recommend and we look forward to going out again.

  2. IK

    Indy

    Glen Cove Private Yacht Charter - 43' Azimut Flybridge

    We had an amazing time & would definitely book with Jay and his team again. The boat was better than we expected & had such a good experience enjoying ourselves. Highly recommend!

  3. LM

    Leah

    Charter Sailboat Cruiser Motorsail Yacht, in Stamford, Connecticut

    Marco is the best!! We had an absolute blast going around the sound. The boat was beautiful and Marco answered all our questions. We had the best time and can’t wait to rebook!

  4. MP

    Merritt

    Cruisers 420 Express Cruiser Rental in Long Island Sound

    Captain Dirk and his boat made our Fourth of July one to remember! From the moment we stepped on board, Dirk was the picture of professionalism—warm, respectful, and incredibly knowledgeable. I’m 39 weeks pregnant and felt completely safe and cared for the entire time. The boat itself was pristine, spacious, and so comfortable—perfect for taking in the fireworks in style. Dirk went above and beyond to make sure everyone had a great time. Truly one of the best boating experiences I’ve ever had. Can’t recommend him enough!

  5. TL

    Terry

    Glen Cove Private Yacht Charter - 43' Azimut Flybridge

    Amazing day with Jay’s crew Dino and John. Super friendly, the boat was super clean, comfortable, and modern, and the ride was really smooth. We had an awesome day celebrating a 30th birthday and are already thinking about booking again for something in the future!

  6. KE

    Kethia

    30ft 2022 Pontoon w/ Slide- Stamford, CT! Charter Specialists. Over 3000+ Trips

    Highly recommend to work with Luke and his boats. Great fun ride. Ask for Jackie as a captain. She’s great!