Vacation rentals with a kayak in Sheboygan County

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Top-rated kayak rentals in Sheboygan County

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Top guest favorite

Home in Elkhart Lake

4.98 out of 5 average rating, 82 reviews

Fernwood Lodge: Your Elkhart Lakefront Retreat

Gorgeous lake home on pristine Elkhart Lake. The large deck, screen porch & stone patio all boast gorgeous lake views. Walk down to your private pier and enjoy paddling or lounging by the water. Take a stroll into town on the rustic lake front path. Warm up listening to the fire crackle cozied up on a sofa, or outside by the fire pit. With a chef’s kitchen and extensive amenities, it's perfect for a weekend or extended stay year round! We strive to be inclusive and welcoming. BLM, 🏳️‍🌈🏳️‍⚧️

Guest favorite

The two-story timber cabin features a spacious deck adorned with several blue lounge chairs, overlooking a sandy beach area. Lush greenery and a clear blue sky frame the scene, while the gently sloping landscape leads to a peaceful lake.

Cabin in Cascade

5 out of 5 average rating, 40 reviews

Willows Cabin Cascade, On Lake

Near Kohler, between Green Bay & Milwaukee, this two-story craftsman timber cabin is on a 20 acre non-motorized private lake. With a sand beach and trails this property is wonderful for friends & families. The gated community has a basketball & tennis court, kayaks, canoes, and a dock perfect for dropping a fishing line. Nearby wineries, golf courses such as Whistling Straights, lakes, and Kettle Moraine State Forrest allow guests to relax or explore. Ryder Cup 2020! Ask about 2 & 3 night stays.

Guest favorite

A view from above showcases the rustic cabin, framed by lush greenery and a clear path leading toward the shoreline. The serene lake glistens under a partly cloudy sky, with vibrant autumn foliage visible across the water's edge, creating a peaceful natural setting.

Cabin in Cascade

5 out of 5 average rating, 10 reviews

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 20 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. Book your stay at Highlander Hideaway and embark on a journey of serenity and discovery.

Guest favorite

Home in Sheboygan Falls

4.95 out of 5 average rating, 19 reviews

“On The Water” the Sheboygan River Overlook

The views from inside make it feel as if the home is overhanging the beautiful Sheboygan River. Go kayaking, enjoy the historic downtown, relax in the sunroom warmed by a fireplace, or sit out back on the deck. These are just some of the things this space has to offer. You are between several great golf courses including Whistling Straights & The Bull, & just 15 minutes from Road America. You will love the eclectic comfort & atmosphere of this spacious 2 bedroom 1 1/2 bath home! Memories await!

Top guest favorite

A serene view of Little Elkhart Lake is presented, featuring calm waters reflecting the lush greenery. A wooden dock extends into the water, accompanied by two wooden chairs positioned for relaxation. In the distance, a paddle boat and another dock are visible, enhancing the tranquil setting.

Home in Plymouth

5 out of 5 average rating, 63 reviews

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!

Guest favorite

A private pier extends into the calm waters, lined with colorful kayaks and paddleboards. The spacious lawn offers picnic tables and a view of the lakehouse's modern exterior, framed by lush greenery and tall trees under a clear blue sky.

Cottage in Random Lake

5 out of 5 average rating, 8 reviews

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.

Guest favorite

A serene freshwater lake is visible, bordered by lush trees under a clear blue sky. A sandy beach and docks are seen in the distance, while several outdoor tables and chairs line the waterfront, creating a welcoming space for relaxation.

Hotel room in Elkhart Lake

5 out of 5 average rating, 5 reviews

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!

Top guest favorite

A serene landscape features a calm pond surrounded by lush greenery. A sandy area with kayaks and paddle boards is visible. Two gazebos with domed roofs stand in the yard adjacent to the spacious farmhouse, blending harmoniously with the countryside setting.

Farm stay in Oostburg

4.94 out of 5 average rating, 98 reviews

Blue Barn on the Green and Farmhouse Retreat

Imagine your perfect countryside escape. Nestled on five acres of farmland, this serene retreat offers tranquility and breathtaking views. Enjoy fishing, paddle boarding, or simply relaxing by the pond. For the golf enthusiasts, we're just a short drive from downtown Kohler and other top-rated courses. Our property is ideal for families, couples, or groups seeking a peaceful retreat. We also host unforgettable weddings in this idyllic setting. Contact us today to book your dream getaway!

Top guest favorite

A sandy beach area includes wooden chairs positioned for lake views. A dock extends into the water, where boats are visible. Colorful kayaks and canoes are lined up along the shore, surrounded by greenery and gentle waves under a partly cloudy sky.

Condo in Elkhart Lake

5 out of 5 average rating, 11 reviews

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!

Superhost

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

4.84 out of 5 average rating, 67 reviews

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.

Top guest favorite

A hammock is set between two trees on a grassy area, facing the serene view of Lake Michigan. A spacious guest home with large windows is visible in the background, framed by lush greenery and a clear blue sky.

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

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, 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...

Superhost

A rustic two-story cottage is situated by a tranquil lake, designed with a blend of wood and stone. The expansive deck features seating overlooking the water, while rolling hills provide a natural backdrop under a clear blue sky.

Cabin in Cascade

4.83 out of 5 average rating, 30 reviews

Lakefront Cabin on Private Lake Community

Take it easy at this unique and tranquil getaway. This 2200 square ft. handcrafted two-story open loft cottage on 20-acre non-motorized private spring fed lake with sand beaches & 70 acres of walking trails! Enjoy hiking, swimming, fishing, volleyball, tennis, basketball & water activities. Near Kohler & Elkhart, between Green Bay & Milwaukee. Nearby wineries, golf courses, sportsman clubs, and Kettle Moraine State Forest.