Cabin holiday rentals in Sheboygan

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Family · Value · View

Fernwood Elkhart Lakefront: hot tub, pier, kayaks

Beautiful, serene lakehome on pristine Elkhart Lake. The hot tub, deck, screen porch & stone patio all have gorgeous lake views. The private pier is perfect for a dip, paddling or lounging by the water before basking in a luxurious sunset soak in the hot tub. Enjoy a stroll into the adorable town of Elkhart via the rustic lakefront path. 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🏳️‍🌈

Family · Location · Checkout

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 but mighty house. 2 bedrooms, beautiful kitchen, tree fort style loft, 2nd living/kid room w/ arcade & pinball. Everything you could want. Fish off the pier or use our kayaks to explore the lake. Ride our bikes around town & then cuddle up in front of the fireplace. The village beach is only a few blocks away, so is the bustling downtown. Memories await

Family · Location · Pets

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

Slow down at Fraser Fir log cabin, built in 1858 on Kettle Moraine Lake. In the summer, enjoy quiet moments watching the sun set from the front porch, then relax by the fire pit under a sky full of stars. Fish from the dock, kayak around the lake, or bring your boat to soak up the sun. In the winter, grab your ice-skates or ice-fishing gear and head out on the lake. With countless trails nearby, the hiking options are limitless and beautiful in every season. Your next adventure awaits.

Value · Family · Wi-Fi

Log Cabin At The Lake

This charming rustic-luxe 1946 log cabin brings all the vibes: stunningly-renovated w/ elevated comforts & steps from some of Lake Michigan’s best WI shoreline. This spacious retreat offers 3 bedrooms, 2 ½ baths, and space up to 11. Enjoy beach access, cozy gas fireplace, patio with a hot tub, sauna, & cold plunge circuit, outdoor grill, dining & fire pit. Just off of I-43 & just south of Sheboygan, this up-and-coming area has everything you need for a wonderful vacation any season of the year!

Family · Location · Nearby

Peaceful Lakeview Cabin Stay On Private Peninsula

Tucked on a private peninsula in Wisconsin’s Kettle Moraine, Birchwood Log Cabin is a quiet 4-bedroom, 2-bath retreat with stunning lake views and space for up to 14 guests. Enjoy a wraparound deck, wood-burning fireplace, and open-concept great room for cozy nights in. While our lake is view-only, you’re just a short walk to Kettle Moraine Lake’s public beach, boat launch, and vibrant Tiki Bar. Come for the stillness, stay for the trails, sunsets, and connection. Open year-round. Pets welcome!

Location · Family · View

Cozy Cabin! Fall Hikes, Kayak Getaway! Warm Fires!

Come experience the charm of a sun-drenched A-frame cottage, offering breathtaking sunsets, and serene lake glimpses. Whether cozying up indoors with a book and coffee, or enjoying a warm campfire, with s'mores, indulging in seasonal activities, like fishing, kayaking, ice fishing, or exploring nearby attractions like Solu winery, Tiki Beach, every moment promises blissful relaxation and adventure. With Kettle Moraine State Forest as your backdrop, unforgettable memories await at every turn.

Location · Family · Decor

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 several beautiful golf courses. It has all of the amenities for your memorable family vacation. Sorry no pets.

Family · Location · Nearby

hot tub and sauna on 5 private acres

Looking for a peaceful retreat? Experience 5 acres of tranquil, private woodland paradise. Cool nights are perfect for warming up in the hot tub or infrared sauna which overlook the meadow. Explore hiking trails and lakes that the scenic Kettle Moraine has to offer. Grill a delicious meal and later craft perfect s’mores by campfire as the crickets sing. Unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee. Your getaway awaits!

Family · Value · Biking

Cabin moments away from Road America and Lakes

Just steps from Crystal Lake. This cozy cabin serves as a great base for year round activities in the Kettle Moraine forest area. There are nearby wineries, golf courses, lakes, and winter/summer trails to enjoy. Cabin is located next to Rumors Roadhouse which offers BBQ and live music. Road America, one of the world's fastest permanent road racing tracks, is 5 minutes away. Cabin guest enjoy discounted meals and beverages at Rumors Roadhouse BBQ as part of their stay.

Family · Value · View

Escape to your Private Lakeside Cabin Retreat!

Leave the crowds behind and discover 70+ private acres of forest, trails, and a crystal-clear spring-fed lake that’s yours to enjoy. At Highlander Hideaway, mornings begin with coffee overlooking the water, afternoons are spent kayaking, paddleboarding, hiking, or fishing, and evenings end around the fire beneath a sky full of stars. This isn’t just a cabin. It’s your own private wilderness retreat. No parties allowed, including bachelor and bachelorette parties.

Family · Location · Nearby

The Cabin on Kettlewood Acres - Private Forest

Escape to the peaceful Kettlewood log cabin tucked among rolling kettles and quiet woods. Relax on the front porch swing, sip French press coffee, or unwind by the fire pit. Just a mile from the Parnell Tower and trails, minutes from Solu Winery, and less than 15 minutes from Plymouth for anything you need. Nestled near Mauthe Lake and Long Lake State Parks, adventure awaits in every direction. A true hidden treasure. Take a look and book your stay today.

Location · Family · Nearby