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Springfield, Massachusetts Boat Rentals

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.
Sailing in Salisbury · 2 guests

Captained Charter 21ft Sailboat in Salisbury 2 person charter 2 hrs.

5.0
$85/hour
Captained Sailboat Charter in Salisbury 2 hr sails 4 persons
Sailing in Salisbury · 4 guests

Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

5.0
$160/hour
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
18ft Godfrey Sweetwater Pontoon Rental in Wilmington
Powerboats in Wilmington · 10 guests

18ft Godfrey Sweetwater Pontoon Rental in Wilmington

New
$450/day
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
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
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
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
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
Zippy 17.5ft Bayliner with Trailer
Powerboats in Massachusetts · 7 guests

Zippy 17.5ft Bayliner with Trailer

New
$75/hour
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
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/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
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
Experience the Candlewood Lake in CT
Powerboats in Brookfield · 6 guests

Experience the Candlewood Lake in CT

5.0
$175/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

New
$220+/hour
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

5.0
$165+/hour
Tubing and Water Fun on Candlewood Lake
Powerboats in New Fairfield · 10 guests

Tubing and Water Fun on Candlewood Lake

5.0
$185/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
Adventure Cruise in the Upper Bay onboard 31ft Center Console
Powerboats in Providence · 6 guests

Adventure Cruise in the Upper Bay onboard 31ft Center Console

5.0
$134+/hour
Luxury 62' Lagoon Catamaran
Sailing in Warwick · 12 guests

Luxury 62' Lagoon Catamaran

5.0
$1,325/hour
Providence Boat Tour
Powerboats in Cranston · 5 guests

Providence Boat Tour

New
$150/hour
Explore Narragansett Bay starting in Beautiful E. Greenwich, RI on this 40' MY
Events in East Greenwich · 6 guests

Explore Narragansett Bay starting in Beautiful E. Greenwich, RI on this 40' MY

5.0
$400/hour

Springfield Reviews

  1. 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!

  2. 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!

  3. 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!

  4. WB

    Wayne

    Captained Sailboat Charter in Salisbury 2 hr sails 4 persons

    I really appreciate how Captain Nina accommodated me last minute after I had a lesson scheduled at a sailing school. Saved my plans for the weekend. She did a great job adjusting the experience to my level, and keeping the whole time chill and conversational.

  5. 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 !!!!

  6. JR

    Jai

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

    We had a wonderful experience and found Captain Eric to be an excellent sailor and gracious host. He is extremely friendly, relaxed and a great conversationalist who has many stories to tell about the Thimble Islands and other topics. We had a large party with a two year old child and Captain Eric made us all comfortable and provided us with a perfect trip.