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Winthrop Harbor, Illinois Boat Rentals

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother
Sailing in Kenosha · 6 guests

SAIL aboard "RED WITCH III" -- Kenosha's TALL SHIP RED WITCH'S little brother

New
$175/hour
Kenosha Fishing Charter on 32ft Luhrs Tournament Sportfish
Fishing in Kenosha · 6 guests

Kenosha Fishing Charter on 32ft Luhrs Tournament Sportfish

5.0
$90+/hour
Instant Book
27' Motor Yacht Charter in Waukegan, Illinois
Powerboats in Waukegan · 4 guests

27' Motor Yacht Charter in Waukegan, Illinois

New
$241/hour
Explore the Coast on the 27’ Bayliner Ciera Sunbridge
Powerboats in Waukegan · 4 guests

Explore the Coast on the 27’ Bayliner Ciera Sunbridge

New
$350/hour
Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available
Powerboats in Antioch · 8 guests

Wheelchair Accessible Pontoon Boat Chain-O-Lakes in Illinois Captain available

5.0
$100+/hour
40ft Chris Craft for Fishing or Cruising on Lake Michigan
Fishing in Racine · 6 guests

40ft Chris Craft for Fishing or Cruising on Lake Michigan

5.0
$145/hour
Instant Book
23ft tidewater  Boat Rental in Racine, Wisconsin
Powerboats in Racine · 4 guests

23ft tidewater Boat Rental in Racine, Wisconsin

New
$125/hour
Sail Lake Michigan from Racine, WI
Sailing in Racine · 6 guests

Sail Lake Michigan from Racine, WI

5.0
$75/hour
2022 South Bay 24 foot Tritoon - rent by the day or week
Powerboats in Fox Lake · 14 guests

2022 South Bay 24 foot Tritoon - rent by the day or week

5.0
$145/hour
Twin engine 2023 Scarab Bowrider for Rent in Johnsburg, Illinois
Powerboats in Fox Lake · 7 guests

Twin engine 2023 Scarab Bowrider for Rent in Johnsburg, Illinois

5.0
$125/hour
Instant Book
Beautiful Deck Boat with captain on Lake Zurich
Powerboats in Lake Zurich · 6 guests

Beautiful Deck Boat with captain on Lake Zurich

New
$185/hour
Lake Tichigan Pontoon Boat Waterford (30 mins from MKE), no tubing, min 3hrs
Powerboats in Wisconsin · 10 guests

Lake Tichigan Pontoon Boat Waterford (30 mins from MKE), no tubing, min 3hrs

5.0
$70/hour
Party Bennington Chartered Boat Rental
Powerboats in Williams Bay · 12 guests

Party Bennington Chartered Boat Rental

5.0
$175+/hour
22ft Four Winns for rent on Lake Geneva Region  Cannot leave the state of WI
Powerboats in Williams Bay · 10 guests

22ft Four Winns for rent on Lake Geneva Region Cannot leave the state of WI

5.0
$90+/hour
Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable
Events in Chicago · 8 guests

Premium 28' Larson Cabrio with Ultra Loud Speakers and the Ultimate Inflatable

New
Snoozed - Active 02 Oct 2025
23' Moomba Mojo Party Boat on Geneva Lake
Powerboats in Williams Bay · 12 guests

23' Moomba Mojo Party Boat on Geneva Lake

5.0
$250+/hour
2023 Sea Doo Switch Cruise -Cannot leave the state of WI - No Shallow Lakes
Powerboats in Williams Bay · 10 guests

2023 Sea Doo Switch Cruise -Cannot leave the state of WI - No Shallow Lakes

5.0
Snoozed - Active 02 Oct 2025
Bennington Pontoons Rental in Lake Geneva, Wisconsin
Powerboats in Williams Bay · 12 guests

Bennington Pontoons Rental in Lake Geneva, Wisconsin

4.4
$165/hour
Mastercraft Maristar 23ft Boat for Rent on Lake Geneva
Powerboats in Williams Bay · 10 guests

Mastercraft Maristar 23ft Boat for Rent on Lake Geneva

4.0
$165/hour
Godfrey Sweetwater 20ft Portable pontoon in Mukwonago, Wisconsin
Powerboats in Wisconsin · 8 guests

Godfrey Sweetwater 20ft Portable pontoon in Mukwonago, Wisconsin

5.0
$215+/day
Oceanis 393 Beneteau Sailing Yacht Rental in Chicago
Sailing in Chicago · 10 guests

Oceanis 393 Beneteau Sailing Yacht Rental in Chicago

New
$275/hour
Full Service Tritoon Boat Charter On Geneva Lake
Powerboats in Williams Bay · 12 guests

Full Service Tritoon Boat Charter On Geneva Lake

New
$200/hour
Flawless 2024 68' Sunseeker Manhattan
Events in Chicago · 12 guests

Flawless 2024 68' Sunseeker Manhattan

New
Snoozed - Active 02 Jan 2026
LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)
Events in Chicago · 13 guests

LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

5.0
Superowner
Best of 2025
$250/hour

Winthrop Harbor Reviews

  1. ava

    ava

    23' Moomba Mojo Party Boat on Geneva Lake

    We booked this boat for a bachelorette trip on Lake Geneva and had the best time! The boat was spacious, clean, and perfect for relaxing, taking in the views, and celebrating. The crew made everything super easy and enjoyable. Highly recommend for a fun and memorable day on the lake!

  2. AX

    Andrew

    LUXURY Multi Level Meridian Yacht! Water Toys Included - Chicago, IL (I)

    Shay and team were one of the best folks to charter in Chicago from. Along with the rapid responsiveness, the general helpfulness, and especially providing a captain priced for the charter, just made everything so much easier and funner!!

  3. PG

    Paul

    2023 Sea Doo Switch Cruise -Cannot leave the state of WI - No Shallow Lakes

    Jason was simply a fabulous communicator. The boat was first-class, pristine, in perfect condition. Jason made things simple, direct and a pleasure...add to that the lake was great, the directions excellent, the weather fantastic and it was a perfect day!

  4. PG

    Paul

    22ft Four Winns for rent on Lake Geneva Region Cannot leave the state of WI

    Jason and the boat were fantastic. Jason is relaxed but extremely attentive to detail. His boats (we rented twice from him, with similarly excellent results) are top-notch, pristine, in perfect condition. Jason was a superb communicator, and we always knew what to do, when/where to meet him etc. We'll rent from him again (and again, and again).

  5. JW

    Jody

    2023 Sea Doo Switch Cruise -Cannot leave the state of WI - No Shallow Lakes

    We took my daughter and a few of her friends out on Lake Geneva for the day. They all loved the boat, tubing, and the working with Jason was a pleasure! Thank you and we look forward to our next boat trip!

  6. FC

    Francis

    2023 Sea Doo Switch Cruise -Cannot leave the state of WI - No Shallow Lakes

    Jason was great to work with. He was very accommodating and helpful in getting everything set up. Would highly recommend Jason’s rentals and will definitely look to rent from him again moving forward.