Vacation rentals with a kayak in Sheboygan County

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Top-rated kayak rentals in Sheboygan County

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Guest favorite

Cabin in Cascade

5.0 out of 5 average rating, 36 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.

Nov 15 – 22

$653 per night

Guest favorite

Townhouse in Sheboygan

5.0 out of 5 average rating, 20 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.

Oct 20 – 27

$296 per night

Guest favorite

Home in Plymouth

5.0 out of 5 average rating, 51 reviews

Lakeside Luxury. Walk to Road America+Hot Tub

Beautiful lake home located directly on Little Elkhart Lake. Home features 3 bedrooms, 2 full bathrooms & 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 is great for cooler evenings & of course s’mores. Come enjoy this little Piece of paradise!

Oct 11 – 18

$548 per night

Guest favorite

Cabin in Plymouth

5.0 out of 5 average rating, 26 reviews

The Cottage at Crystal Lake

Nestled in the woods on Crystal Lake in Sheboygan County, Wisconsin. Newly renovated with two full baths and one half-bath, sleeps up to eight, two fireplaces, terraced patios, WiFi, and a cozy pub with a wood burning stove. DOGS ARE WELCOME! We know what it is like to want to travel with your four-legged kids. Now you can with a fenced-in yard and easy-to-clean floors! Our place is good for couples, families (with kids), and furry friends (pets). We are dog friendly and gay friendly!

Sep 17 – 24

$366 per night

Guest favorite

Farm stay in Oostburg

4.93 out of 5 average rating, 87 reviews

Peaceful Country Escape - Fun and Nature Awaits!

This countryside retreat complete with one acre pond is your perfect family weekend get-away or perfect home base for the annual golf trip with family & friends and the perfect place for a quiet retreat away from the hustle and bustle of the big city! We are nestled on five acres, surrounded by another 40 acres of farmland, just minutes off Interstate Hwy 43, and a short drive to Lake Michigan. We do host weddings as well! Please send a message when inquiring for a wedding. Thank you.

Feb 16 – 23

$608 per night

Guest favorite

Cabin in Random Lake

4.97 out of 5 average rating, 65 reviews

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 historic house. Two bedrooms, beautiful kitchen, tree fort style loft, four seasons kid room, everything you could want. Fish off the pier or use our kayaks to explore the lake. Ride our bicycles around town and then cuddle up in front of the fireplace. The village beach is only a few blocks away, so is the bustling downtown of Random Lake.

Oct 29 – Nov 5

$206 per night

Guest favorite

Home in Elkhart Lake

4.97 out of 5 average rating, 71 reviews

Spacious Lakefront Home, Private Pier

We strive to be inclusive and welcoming. BLM, 🏳️‍🌈🏳️‍⚧️ Spacious, fully updated lake home on pristine Elkhart Lake. You’ll have a large, partially screened-in deck with lake views for eating meals or just relaxing. Walk down the stairs to your private pier and enjoy a swim or a sunset beverage. With the well equipped kitchen and amenities, it's perfect for a weekend or extended stay year round! As we are constantly updating and improving the property, photos may not be up to date.

Oct 16 – 23

$463 per night

Guest favorite

Home in Oostburg

4.96 out of 5 average rating, 164 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...

Sep 3 – 10

$410 per night

Guest favorite

Cabin in Cascade

4.93 out of 5 average rating, 14 reviews

This is the place! Lakefront cabin for big family

Relax with the whole family at this peaceful lakefront cabin! Wake up to stunning views and days filled with kayaking, hiking, s’mores by the fire pit. The Bird House at the Willows has everything you need for an incredible get away for two or your whole family! **The Willows is a tranquil, family oriented vacation experience. As such, The Bird House is a family rental only. Bachelor/Bachelorette parties are not permitted. **

Nov 14 – 21

$608 per night

Guest favorite

Cabin in Cascade

4.89 out of 5 average rating, 18 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.

Jan 6 – 13

$398 per night

Guest favorite

Home in Sheboygan

4.97 out of 5 average rating, 115 reviews

Lake Michigan home with gorgeous views!

Our beautiful lakefront home is perfect for bringing everyone together - Ladies weekend, guys golf trip, family reunion, Packers games...this is your place. Minutes to downtown Sheboygan/Kohler, with 5 star PGA championship golf courses (Black Wolf Run, Whistling Straits, The Bull of Pinehurst), Kohler Waters Spa, and the beaches/dunes of Kohler Andrae State Park. Renovated bedroom and movie room completed early 2020.

Nov 14 – 21

$460 per night

Superhost

Cottage in Random Lake

4.86 out of 5 average rating, 42 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, 4 TVs with cable (including Netflix and Disney +), 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.

Feb 6 – 13

$275 per night