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

A wooden hot tub is nestled among tall trees, providing a serene retreat. Natural stone steps lead to the tub area, with views of the water visible through the foliage. A neatly stacked pile of firewood rests nearby, enhancing the outdoor aesthetic.

Home in Elkhart Lake

4.98 out of 5 average rating, 90 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, 🏳️‍🌈🏳️‍⚧️

Top guest favorite

A serene riverside view is framed by tall trees, showcasing a natural pathway leading to the water. A circular stone firepit is visible, complemented by two small white chairs, providing an inviting outdoor seating area.

Home in Sheboygan Falls

4.97 out of 5 average rating, 35 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

Two black Adirondack chairs are positioned on a wooden deck overlooking a calm lake. A small side table sits between them, providing a perfect spot for refreshments. Lush greenery surrounds the lake, reflecting the serene landscape under a clear blue sky.

Home in Plymouth

5 out of 5 average rating, 68 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

An open living area showcases a comfortable seating arrangement with a light grey sofa and coordinating armchairs. A coffee table is centrally placed atop a textured rug, and a modern kitchen with a bar area features sleek cabinetry and pendant lighting. Natural light fills the space from large windows.

Townhouse in Sheboygan

5 out of 5 average rating, 47 reviews

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.

Guest favorite

An aerial view showcases the cabin nestled among lush greenery, adjacent to a serene lake. A well-maintained path leads from the home to the water's edge, framed by trees reflecting vibrant autumn colors. The peaceful landscape invites relaxation and exploration.

Cabin in Cascade

5 out of 5 average rating, 17 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 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.

Superhost

An outdoor seating area features a large rectangular table surrounded by multiple chairs. An umbrella provides shade over the dining space, with lush greenery and a clear view of the lake in the background, enhancing the tranquil atmosphere.

Cottage in Random Lake

4.91 out of 5 average rating, 11 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 well-lit room features two spacious beds dressed in crisp white linens. A flat-screen television is mounted on the wall, while a dresser provides storage. A small desk is set against one wall, accompanied by a decorative indoor plant in a pot.

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!

Guest favorite

A deck furnished with wooden chairs offers a view of the reflective lake surrounded by vibrant autumn foliage. Colorful trees frame the water, enhancing the natural setting. Tables and seating are visible in the open space below, providing areas for gathering.

Cabin in Plymouth

5 out of 5 average rating, 16 reviews

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.

Guest favorite

A calm pond reflects the surrounding trees and buildings under a clear blue sky. The landscape showcases a blend of greenery and structures, creating a serene atmosphere. The still water enhances the tranquility of the countryside setting.

Farm stay in Oostburg

4.94 out of 5 average rating, 101 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

An aerial view captures the expansive waters of Elkhart Lake, with shimmering reflections of sunlight. The shoreline is lined with lush greenery and a sandy beach, complemented by a few boats gently floating on the surface. Nearby, various residential structures can be seen nestled among the trees.

Condo in Elkhart Lake

5 out of 5 average rating, 19 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

4.86 out of 5 average rating, 77 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 spacious guest home is set against a backdrop of tall trees, positioned near a sandy beach. The exterior features a covered porch and two lounge chairs, inviting relaxation while enjoying the serene landscape.

Home in Oostburg

4.96 out of 5 average rating, 196 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...