Vacation rentals with a hot tub in Sheboygan County

Schoolhouse Straight Inn-three level school

Welcome back to school! This rustic remodel of 1925 schoolhouse has two full apartments, rented together or separately. Located on Elkhart's original road track just off the Ice age trail. Great for family reunions, special occasions, golf outings, team building or racing teams! Upper garage deck with Hot tub running year round. Large whirlpool tub with bath salts in upper bath. Keep your eyes out for cool cars still driving the track! There are country views through out the 3,000 sq ft space.

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

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!

hot tub and sauna on 5 private acres

Need 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 inspired getaway awaits!

Helene's room

Our 4-room B&B is the perfect couple's retreat, located on a working aquaponics farm on the shores of Lake Michigan. Fresh farm breakfasts are included daily. Enjoy our complimentary 9 hole golf course and foot golf course. Free wi-fi and satellite TV. Common area game room includes pool table, bar area, and satellite TV. Family friendly cottage is ideal for family reunions & parties. Event barn is available for weddings & other events from May - October. Call us for more information

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.

Private Home 4 BR+2Ba, Heated Pool by Road America

Family friendly, private home in Plymouth, WI. Approx. 4 miles to Road America. A beautiful Two-Story, 4 bedroom, 2 bath home with outdoor heated private pool, hot tub, gas grill and an outdoor pavilion available June - Labor Day. Close to Plymouth Dirt Track, Golf Courses, 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.

Riverwoods Retreat | Game Room, Hot Tub & Sauna

Escape to Riverwoods Retreat, a luxury getaway in the heart of Sheboygan County! Just minutes from Road America, Elkhart Lake, and Whistling Straits, this 4-bedroom home sleeps 10 and features a PS5 game room, racing arcade, hot tub, sauna, and massive deck with a grill gazebo. Fully renovated with brand-new furnishings and stylish decor. Perfect for families, golf trips, or weekend escapes—relax, recharge, and explore all SE Wisconsin has to offer!