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Middletown, Connecticut Boat Rentals

Sea Ray 39ft Yacht Charter in Deep River.  A great day on the water !
Events in Clinton · 6 guests

Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

5.0
$175+/hour
Rent a Celebrity Cruiser with Captain included in price
Water Sports in New Haven · 9 guests

Rent a Celebrity Cruiser with Captain included in price

New
$200/hour
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/hour
Luxury with No Limits - 43' Mystic Center Console
Powerboats in Old Saybrook · 13 guests

Luxury with No Limits - 43' Mystic Center Console

5.0
$800/hour
Overspray in Old Saybrook | 37ft Silverton Yacht
Powerboats in Old Saybrook · 6 guests

Overspray in Old Saybrook | 37ft Silverton Yacht

5.0
$300/hour
Instant Book
85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island
Events in Old Saybrook · 12 guests

85 Pacific Mariner-Serving Luxury to Connecticut and Eastern Long Island

New
$2,250+/hour
20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar
Powerboats in Connecticut · 7 guests

20ft Nautique Ski Boat: Ski Instruction, Tubing, Fishing and Fun on Lake Zoar

5.0
$140/hour
Instant Book
Sail to Fishers Island on a fast and classy 35' Sailboat
Sailing in New London · 6 guests

Sail to Fishers Island on a fast and classy 35' Sailboat

5.0
Snoozed - Active 02 Jun 2026
Captained sail on a beautiful and comfortable 50' wooden ketch
Sailing in Greenport · 6 guests

Captained sail on a beautiful and comfortable 50' wooden ketch

New
$475/hour
40 Foot Tiara Motor Yacht Rental in Greenport, New York
Powerboats in Greenport · 6 guests

40 Foot Tiara Motor Yacht Rental in Greenport, New York

New
$600/hour
31’ Bertram Classic with captain. Greenport NY
Events in Greenport · 6 guests

31’ Bertram Classic with captain. Greenport NY

5.0
$250/hour
Instant Book
💎 VIP experience - Vanquish VQ40 + SeaBob Rental in Greenport, New York
Events in Greenport · 12 guests

💎 VIP experience - Vanquish VQ40 + SeaBob Rental in Greenport, New York

New
$875+/hour
💎 VIP Experience: Sanlorenzo 88SX + SeaBob - NY
Events in Greenport · 12 guests

💎 VIP Experience: Sanlorenzo 88SX + SeaBob - NY

New
$2,063+/hour
Ride the Waves in Style with our 26ft Chaparral Surf Boat
Powerboats in Greenport West · 6 guests

Ride the Waves in Style with our 26ft Chaparral Surf Boat

New
$500+/hour
36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island
Sailing in Stonington · 6 guests

36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

5.0
$220+/hour
Swim, cruise, sightsee, & TUBING! Dogs welcome! Lake Lillinonah, New Milford
Powerboats in New Milford · 12 guests

Swim, cruise, sightsee, & TUBING! Dogs welcome! Lake Lillinonah, New Milford

New
$215/hour
Wakesurfing, Tubing, Wakeboaring,Waterskiing, Lake Cruises on Lake Lillinonah
Events in New Milford · 6 guests

Wakesurfing, Tubing, Wakeboaring,Waterskiing, Lake Cruises on Lake Lillinonah

New
$260/hour
Experience the Nautique G23 Paragon Surf, Wakeboard, or Just Hang Out
Powerboats in New Milford · 8 guests

Experience the Nautique G23 Paragon Surf, Wakeboard, or Just Hang Out

5.0
$275+/hour
Experience the Candlewood Lake in CT
Powerboats in Brookfield · 6 guests

Experience the Candlewood Lake in CT

5.0
$175/hour
Able Custom 42' Chartered Sailing Experience in Stonington, CT
Sailing in Stonington · 3 guests

Able Custom 42' Chartered Sailing Experience in Stonington, CT

New
$200+/hour
44' 2023 Solaris + 2 Seabobs Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

44' 2023 Solaris + 2 Seabobs Yacht Charter in Sag Harbor, New York

New
$1,463/hour
43' 2021 Pardo + Seabob Yacht Charter in Sag Harbor, New York
Events in Sag Harbor · 12 guests

43' 2021 Pardo + Seabob Yacht Charter in Sag Harbor, New York

New
$1,482/hour
 32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York
Events in Sag Harbor · 12 guests

32' 2020 Sundancer + Seabob Yacht Rental in Sag Harbor, New York

5.0
$1,063/hour
29' 2021 Yacht Hampton Escape Boat Rental in Sag Harbor, New York
Powerboats in Sag Harbor · 10 guests

29' 2021 Yacht Hampton Escape Boat Rental in Sag Harbor, New York

New
$743/hour

Middletown Reviews

  1. KF

    Karly

    36ft Beneteau Private Sailing Charter – Explore Mystic and Fisher's Island

    We booked a 2 hour boat trip to celebrate my parents retirement and Francisco was amazing! The boat was beautiful, clean and exactly as listed. He was an incredibly gracious host and took us on a lovely sail! Will definitely be back!

  2. MN

    Matinela

    Experience the Candlewood Lake in CT

    We’ve rented boats before in Candlewood lake that we would take out by ourselves, but this experience was on another level. From start to finish, everything was so much better than expected. Our captain took incredible care of us, had everything perfectly planned and organized, and truly exceeded our expectations tenfold. The boat was spotless and well maintained, and the whole trip was seamless and enjoyable. Without a doubt, this was the best boating experience we’ve had, and we’d love to do it again!

  3. DK

    Dmitri

    Charter 36ft Sloop In Westbrook, Connecticut

    We had a fantastic 2-hour sail out of Westbrook! The boat was in great shape, and Captain Joy was a Joy to sail with: she was professional, friendly, and very experienced. She made us feel safe and relaxed the entire time, and even shared some interesting local facts and recommendations along the way. The views were beautiful and the whole trip was smooth and enjoyable. Highly recommend booking with this captain – we’ll definitely be back!

  4. JL

    Jaclyn

    Overspray in Old Saybrook | 37ft Silverton Yacht

    We had a beautiful day out on the CT river for my sister’s birthday! Pick up/drop off was incredibly easy, boat was in great condition, and the crew was very accommodating - would definitely recommend!

  5. FT

    Farry

  6. CV

    Cheryl

    Sea Ray 39ft Yacht Charter in Deep River. A great day on the water !

    Rob and mellie were amazing, they made our boat excursion for a 40th bday extra special, with so many great touches. Mellie was so great helping with our theme and putting together food and drinks for us. She went above and beyond. Rob was great at communicating with me during the whole planning process and answered all my questions . We never felt rushed and they made sure we had good time , we will be booking again next summer , can't wait !!!!