Vacation rentals with a kayak in Sheboygan County

The Random Cabin (On Random Lake)

Suprising Waterfront Cozy Unique Rustic Modern. These all describe the Random Cabin. In the small inviting village of Random Lake sits a small but mighty house. 2 bedrooms, beautiful kitchen, tree fort style loft, 2nd living/kid room w/ arcade & pinball. Everything you could want. Fish off the pier or use our kayaks to explore the lake. Ride our bikes around town & then cuddle up in front of the fireplace. The village beach is only a few blocks away, so is the bustling downtown. Memories await

Dead End Dream House

Welcome to the Dead End Dream House—a peaceful, modern retreat built in 2023. Located at the end of a quiet street, this clean, bright home features 3 bedrooms, 2 full baths, and a spacious backyard—perfect for kids to play and grown-ups to unwind. Take a 10-minute walk to the public beach or stroll downtown for a bite to eat. Back at the house, enjoy evenings under the stars and fall asleep to the sound of frogs in the woods. Whether you're here to relax or reconnect, you'll feel right at home.

Lake living at Road America

Time to get your 2026 Road America accomodation booked. This beautiful property boasts 4 bedrooms and 3 1/2 bathrooms on beautiful Little Elkhart Lake. At just .4 miles from Road America, this is the perfect location for racers or fans looking to relax after a long day at the track. This property boasts a private dock and oversized deck overlooking the lake. Guests can enjoy the complimentary paddle boat or kayaks. Enjoy the fire pit while overlooking the lake from tour perched vantage point.

Paddock Point Lakehouse. Road America+Hot Tub

Welcome to Paddock Point Lakehouse! Located on Little Elkhart Lake. There are 3 bedrooms, 2 full baths & 2 spacious living areas. The upper living room leads to a large deck w/ an outdoor dining table that comfortably seats 6. From the deck enjoy the sunrise & breath taking waterfront views. Lower patio features a charcoal grill & a very relaxing hot tub. There is a fire pit in the backyard that seats 8. Road America’s main gate is across the street, less than a 2 min. drive. Lake life awaits!

Riverfront Sheboygan Townhome w/ Grill!

Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. This 2-story Sheboygan vacation rental is the perfect place to spend time on the water, with on-site river access and proximity to beaches lining the shores of the lake close by. Take the kayak and paddleboard out for a peaceful ride, stroll the boardwalk through the sand dunes and golden beach of Kohler-Andrae State Park, or walk downtown to explore the museums and nightlife.

Cozy Lakefront Escape: Ideal Seasonal Getaway

Nestled on the picturesque point of Random Lake, Wisconsin, our inviting and family-friendly lakehouse offers a perfect blend of natural beauty and modern comfort. Boasting breathtaking lakefront views, a private pier for fishing and boating, and a charming patio adorned with string lights, this retreat is designed to create unforgettable memories. Ideal for large families or groups, our lakehouse can accommodate up to 13 guests and provides all the amenities you need for a relaxing getaway.

Lakeside Cabin Retreat Relax at Private Lake House

Welcome to Highlander Hideaway, where the extraordinary meets the serene. Nestled in a longhouse-style architecture with an abundance of windows that frame captivating views of the lake just feet from the shore, you will find yourself immersed in natural beauty from the moment you arrive. Relax and unwind in your home away from home with all the modern comforts and amenities, and proximity to everything. We do not allow parties, including bachelor/bachelorette parties. Book your stay now!

Walking distance to Road America, Lakefront

Nestled in the woods, you will find fun for the whole family. Our Little Elkhart lakefront cottage has two bedrooms that can easily sleep six guest. We offer kayacking, biking, swimming, an outdoor fire pit, two decks overlooking the lake, and highspeed internet service. This cottage sits on 3/4 acres less than 1 mile from Road America, 4 miles from downtown Elkhart Lake, and minutes from several beautiful golf courses. It has all of the amenities for your memorable family vacation.

Lakefront Condo, Private Beach/Pools, Walk to Town

Elkhart Lake’s beauty awaits year-round! This 3BR/3BA condo boasts a 600 ft private beach, pools (indoor & outdoor), hot tub, water sports rentals, Tiki Bar, and easy access to hiking, golfing, and town. Fall brings vibrant foliage, trail hiking, and golf on scenic courses. Winter offers cross-country skiing, snowshoeing, ice skating, sledding and trail hiking, while spring delights with blooming wildflowers, birdwatching, and farmers markets. Experience nature’s magic any season!

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights ,and magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Lake Front Cottage With Dock. Walk to Road America

Do you like tranquil, peaceful and serene? Don’t miss out on our lake front house. Huge windows with lake views and lots of natural light. Walking distance to Road America. Relax by our outdoor fire pit. Fish or kayak off or dock or swim within 900 ft of the driveway. Enjoy our game room with Pac-man video console or play corn hole. Quiet and relaxing but minutes to the Kettle trails and Historic downtown Elkhart Lake.