Holiday rentals with a hot tub in Sheboygan County

Fernwood Elkhart Lakefront Retreat w/ Pier, kayaks

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, 🏳️‍🌈🏳️‍⚧️

The LODGE in Elkhart Lake. —-Hot Tub & Arcade—-

Rustic modern home w/ hot tub, arcade & fireplace right on the edge of Elkhart Lake. Road America, great golf, The Ice Age Trail, & the Kettle Moraine are all at your doorstep. This cozy home is 4 blocks from the downtown of Elkhart lake. Yet it still has an acre to explore & enjoy nature. Only 4 miles from Road America. 2 bedroom w/ 2 extra sofa sleepers & 2 baths. Perfect for racers or romantic getaways. The arcade/Pinball room has over 10 games. Perfect base camp. We got your bases covered

The Woods Estate walk to RoadAmerica modern luxury

Experience the beauty & luxury of this contemporary home right across the street from Road America and near Kohler Golf! It’s peaceful and relaxing built amongst nature on 6 acres. Spacious 3 living rooms & 4 bedrooms (5 beds - 1 King, 3 queens, 1 full) Kid friendly kid play area Free WiFi (Disney, netflix, Amazon prime) Across the street from Road America. 14 mile to Whistling Straits, 10 min to Kohler, 4 min to Elkhart Lake & Plymouth, couple min to get on Kettle Moraine hiking trails.

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!

Lakeview Beach Bungalow - With outdoor Hot Tub!

Enjoy the Holidays at this Beautifully updated beach house just one block off of Lake Michigan. Enjoy the newly landscaped backyard with pergola & 6 person Hot Tub! Watch the sunrise $ sunset from the second floor master balcony. Walk to the lake across the street and enjoy the wind surfers and beach. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach. .

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!

The Lake Street Kickback in Elkhart Lake!

Welcome to The Lake Street Kickback! This privately owned studio condo is located at The Shore Club of Wisconsin & has access to all resort amenities. During your stay enjoy the outdoor pool/hot tub, resort beach, Tiki bar, on site restaurant, indoor pool & game room. A unique blend of updates, convenience, comfort & relaxation. Just steps away from local favorites including village restaurants, bars, farmers market, shops & neighboring resorts like Osthoff and Siebkens Resorts.

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

Holiday Home for 8ppl w/ Hot Tub in Plymouth, WI

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 4 bedroom, 2 bath home with an outdoor hot tub. Close to grocery stores, various local events, bars, restaurants, and child-friendly places within walking distance. NO PETS allowed on property. *For Long Stays over 7 days, please contact us. HOLIDAY DECORATIONS for NOV-DEC 2025 BOOKINGS! Ready to host families in town for the holidays! Book today!

Oma's Beach House

Your family will love being right across the street from the lake and village beach. You can fish from the public pier or kayak and swim on a beautiful lake. In the backyard you can soak in the hot tub, enjoy the fire pit or relax in the beautiful gardens. In the evening you can watch the sunset over the lake right from your front porch or picture window. Oma’s beach house offers a fun and relaxing vacation experience.

River Ridge | Game Lounge, Theater& Hot Tub Escape

Escape to River Ridge South! 🌟 5 bedrooms + loft | Sleeps 14 MAX 🛁 Private hot tub w/ river views 🎮 Arcade lounge: Golden Tee, Skee-Ball, Air Hockey, PS5 🍿 Theater w/ luxe seating & sound 🔥 Outdoor fire pit & gazebo 🏌️‍♂️ Mins to Kohler golf (Whistling Straits, Blackwolf Run) 🏁 Short drive to Road America 🌳 4 private acres along Onion River Book your Wisconsin Getaway today!

Spacious Home - 4 BR/2.5 Bath + Hot Tub + Game Rm

Family friendly large home in the country with lots of room for fun inside and out. Enjoy everything Sheboygan County has to offer: close to Road America, Golf Courses, Solu Winery, and Kohler-Andrae State Park. An easy drive to Lambeau Field or Milwaukee. NO PETS allowed on property. Fast & reliable Wifi.