Vacation rentals with a kayak in Sheboygan County

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Popular amenities for Sheboygan County kayak rentals

House rentals with a kayak

Cottage rentals with a kayak

A charming cottage is set against a lush green backdrop, featuring a landscaped yard and a circular fire pit surrounded by blue adirondack chairs. A patio with an umbrella can be seen, contributing to the outdoor leisure space.
Cottage in Plymouth
4.75 out of 5 average rating, 4 reviews

Crystal Lake Cottage: Kayaks & Fire Pit!

KellyeRating, 5 stars25 months ago
Lovely lake house, beautiful sunsets in the lake very peaceful. Just a few minutes to Road America Race way which was perfect for us! Thank you for letting us stay hope to see you again soon!
Guest favorite
A spacious deck features a hot tub and seating area with two armchairs and a coffee table. Lush greenery surrounds the space, offering serene views of Crystal Lake. Soft lighting strung overhead enhances the welcoming atmosphere.
Cottage in Plymouth
4.94 out of 5 average rating, 35 reviews

Lakefront Plymouth Cottage w/ Private Hot Tub

NoelRating, 5 stars2 weeks ago
Beautiful place, good restaurants in Elkhart Lake and five minutes away from Road America. We stayed here while attending the races. Peaceful, did not hear any of the noise from the track.
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, 9 reviews

Cozy Lakefront Escape: Ideal Seasonal Getaway

CheyanneRating, 5 stars5 months ago
Such a beautiful and peaceful place. Host is very friendly and responsive. First time I’ve woken up feeling well rested in a minute, beds really helped any of our back issues. Main parking spots might not be available at first due to people parking there for ice fishing on the lake but plenty of street parking. If staying in the winter, run the water for a moment to run through any sediment in the pipes. (Not a house problem, just winter in Wisconsin.) :)
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, 68 reviews

Private 3 bedroom lake house

JosephRating, 5 stars2 days ago
Very nice place and location. Property was as described. Great place for entertaining. Thank you.

Cabin rentals with a kayak

Top guest favorite
The serene lakefront cabin is depicted, showcasing a wooden exterior that reflects in the calm water. Lush greenery surrounds the home, and the clear blue sky adds to the peaceful atmosphere. Balconies and windows enhance the cabin's inviting structure.
Cabin in Cascade
4.95 out of 5 average rating, 20 reviews

This is the place! Lakefront cabin for big family

CaitlinRating, 5 stars3 months ago
Our groups have been staying at Jennie's place for the last several years and always look forward to returning. The house is great for groups - lots of living and sleeping space for everyone. The set up is super fun with different floors and spaces to enjoy. The backyard is great for having a bbq or a campfire right on the lake. The area is nice and quiet as well as beautiful. Our groups are always impressed as soon as we pull up! The hosts are always available to answer quesitons and offer information and they always respond to emails/text super fast. We will definitely keep booking here!
An A-frame cottage is shown surrounded by green trees. The exterior features a rich red wooden finish, complemented by a wooden deck with steps leading up to it. A welcoming sculpture stands beside a dog on the grass, and various outdoor decorations are visible.
Cabin in Cascade
4.8 out of 5 average rating, 5 reviews

Sunset Views by Long Lake

DeniseRating, 5 stars8 months ago
The first words out of our 19 year old’s mouth was, “Mom, this is the best one we have ever stayed in!” Everyone loved how cozy the place felt and how you could set the temp for each room, just the way you liked it, including in the bathroom if the morning was a bit chilly. The rustic charm is just beyond beautiful. I loved the swing set and sitting area around back. Our dog loved it. Overall, just an absolutely gorgeous place to be for an entire week. The beds were clean and comfortable. I would highly recommend to anyone looking for a nice get away.
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

SabrinaRating, 5 stars10 months ago
We loved our stay in Cascade! The house was beautiful and the outdoor area was so peaceful and relaxing. Carla provided helpful and clear information, and she made our stay comfortable with thoughtful extra touches. It was the perfect spot for our family vacation!
Guest favorite
A serene view features the sun setting over a calm lake, reflecting warm tones on the water. Silhouettes of ducks can be seen peacefully swimming, while distant trees line the shoreline, creating a tranquil atmosphere.
Cabin in Random Lake
4.95 out of 5 average rating, 94 reviews

The Random Cabin (On Random Lake)

CathyRating, 5 stars2 weeks ago
It was a nice place, beautiful scenery, close to towns I need to go. The only thing was his neighbor was,asking questions, that he did not need to.
Superhost
A well-organized shelf space features a variety of decorative items, including colorful mugs, woven baskets, and glassware. A round mirror reflects light, while a neutral background complements the rustic wooden shelves. Practical items such as a clock and a coffee maker are also displayed.
Cabin in Plymouth
5 out of 5 average rating, 4 reviews

<><>DayDream Lodge<><> “@ Racers Ridge”

LeaRating, 5 stars1 day ago
Peaceful Retreat in the Perfect Location We absolutely loved our stay! The location was ideal—just a short walk from the lake and tucked in a peaceful, quiet setting that was exactly what we needed to unplug and relax. The home itself was spacious, beautifully decorated, and equipped with everything we needed for a comfortable stay. We spent time exploring the charming downtown shops and discovered a fantastic wine and cheese store. One of our favorite moments was sitting outside, sipping wine, enjoying our cheese, and finishing off the evening with a trip to a great little ice cream shop nearby. We also treated ourselves to massages at the Osthoff, which made the weekend even more rejuvenating. This place truly offered the perfect blend of calm and convenience. Dan was incredibly responsive and helpful throughout the entire stay. We would absolutely come back—highly recommend for anyone looking for some chill time. We would come back for Road America as well, they just were not racing

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