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.

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!

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.

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

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!

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...