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Westfield, Massachusetts Boat Rentals

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
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
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
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
18ft Godfrey Sweetwater Pontoon Rental in Wilmington
Powerboats in Wilmington · 10 guests

18ft Godfrey Sweetwater Pontoon Rental in Wilmington

New
$450/day
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
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
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
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
Experience the Candlewood Lake in CT
Powerboats in Brookfield · 6 guests

Experience the Candlewood Lake in CT

5.0
$175/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
Slide Pontoon on Candlewood Lake
Powerboats in New Fairfield · 8 guests

Slide Pontoon on Candlewood Lake

5.0
$165+/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
Charter 36ft Sloop In Westbrook, Connecticut
Sailing in Westbrook · 6 guests

Charter 36ft Sloop In Westbrook, Connecticut

5.0
$250/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
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
Zippy 17.5ft Bayliner with Trailer
Powerboats in Massachusetts · 7 guests

Zippy 17.5ft Bayliner with Trailer

New
$75/hour
Cruising Monohull Rental in Kingston
Sailing in Kingston · 6 guests

Cruising Monohull Rental in Kingston

5.0
$125/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
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
Spend sunset on Long Island sound | 28ft Bertram Sportfisher Yacht
Fishing in Fairfield · 12 guests

Spend sunset on Long Island sound | 28ft Bertram Sportfisher Yacht

5.0
$195/hour
Dinghy Rental in Schenectady, New York
Powerboats in Schenectady · 4 guests

Dinghy Rental in Schenectady, New York

5.0
$50/hour

Westfield Reviews

  1. Tarik

    Tarik

    Cruising Monohull Rental in Kingston

    Great sail. Our captain Rob was very knowledgeable and easy to talk to. He let us help with some of the sailing and then we sat at the front of the boat and enjoy the view. It was a perfect day weather wise. Had a great time overall.

  2. 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!

  3. 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!

  4. DL

    Dana

    Cruising Monohull Rental in Kingston

    Excellent trip, exactly as described if not better! Karin convinced us to sail at sunset and it was absolutely beautiful. Do not hesitate to book!

  5. LF

    Liza

    Cruising Monohull Rental in Kingston

    This was the perfect choice for my birthday boating goal. Captains were incredible, fun and knowledgeable and even the day showed up as perfect. I can’t wait to do this again VERY soon.

  6. 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!