
Vacation rentals with a kayak in Sheboygan County
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Top-rated kayak rentals in Sheboygan County
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Sheboygan County kayak rentals
House rentals with a kayak
Guest favorite

Private room in Plymouth
4.86 out of 5 average rating, 183 reviewsA Bit of the "Lake" right in Town
JulietteRating, 5 stars2 weeks ago
Easy check in. The accommodations were spacious, comfortable, and clean. The neighborhood was very quiet and safe with great walking areas. Thank you!

Home in Plymouth
New place to stayLake House-Kayaks/Paddle Boards/Private Pier
WendyRating, 5 stars2 weeks ago
Gorgeous house right on the water! Less than 5 minutes from Road America. The perfect escape after a long day at the race track.
Top guest favorite

Private room in Cascade
5 out of 5 average rating, 45 reviewsSuite Retreat - Hideaway in the Woods ❤
DonnaRating, 5 stars1 week ago
We usually don’t book rooms within a home, but with limited options during a busy race weekend at Road America, we tried this place—and it was a pleasant surprise! The suite is spacious, clean, and comfortable, and having coffee and cream provided was a thoughtful touch. Mike and Katie were awesome hosts—friendly, helpful, and full of local suggestions. The location was perfect too—just 15 minutes from the track. Would definitely stay again!

Home in Sheboygan Falls
4.92 out of 5 average rating, 13 reviewsRiver Meadow Getaway in Sheboygan Falls
JohnRating, 5 stars34 months ago
Great location with quick access to all attractions in the area. Loved the calm setting of the yard and views from the house, so easy to unwind!
Cottage rentals with a kayak

Cottage in Plymouth
4.75 out of 5 average rating, 4 reviewsCrystal 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

Cottage in Plymouth
4.94 out of 5 average rating, 35 reviewsLakefront 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

Cottage in Random Lake
5 out of 5 average rating, 9 reviewsCozy 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

Cottage in Random Lake
4.84 out of 5 average rating, 68 reviewsPrivate 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

Cabin in Cascade
4.95 out of 5 average rating, 20 reviewsThis 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!

Cabin in Cascade
4.8 out of 5 average rating, 5 reviewsSunset 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

Cabin in Cascade
5 out of 5 average rating, 40 reviewsWillows 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

Cabin in Random Lake
4.95 out of 5 average rating, 94 reviewsThe 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

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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