Vacation rentals with a hot tub in Sheboygan County

Schoolhouse Straight Inn-Penthouse

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

Lakefront Plymouth Cottage w/ Private Hot Tub

Get ready to make a splash when you book this 2-bedroom, 2-bath Plymouth vacation rental! With 3 flat-screen TVs, a fully equipped kitchen, and direct access to Crystal Lake, this property is the perfect home base for family-friendly groups seeking lake life with on-site entertainment galore. Sip your coffee from either deck and relish the peaceful, lake views. Head down to the private pier and kayak or paddleboard with the kids! Cap off your evenings with a soak in the hot tub. It's up to you!

Resort Life 2 Queen Suite

WELCOME RACE FANS AND VACATIONERS!!!! The Victorian Inn is located along a picturesque freshwater lake and within walking distance to exciting events and adventures!Our rooms offer easy access to an indoor pool, outdoor pool, fresh water lake, and so much more! Victorian Inn is situated in the heart of downtown Elkhart Lake near several specialty shops and restaurants. We're also just 2 miles from Road America, 8 miles from Kettle Moraine State Forest, and a short drive to PGA golf courses!

Newly Renovated 4 Bedroom Home

Our beautiful renovated home is your ultimate getaway retreat. The house includes modern touches and has an outdoor feel. The open concept kitchen/family room provides the ideal space for relaxing and includes a spacious backyard and deck with a hottub. The gourmet kitchen has plenty of seating for family. Details include quartz countertops, fireplace, wet bar, Sonos system, and Kohler fixtures. Renovated masterbath and bedroom includes a large shower and double sinks. Sleeps 14+ guests.

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!

Spacious Property, Hot Tub, Sleeps 9, EV Charger

Spring into making memories at The Pines located in the beautiful southern Kettle Moraine Forest area. The property is surrounded by state land. Explore the outdoors by hiking, ATV/UTV riding, fishing on nearby lakes such as Butler Lake, Long Lake, Kettle Moraine Lake. Enjoy the hot tub and smores by the firepit or firetables. Near SoLu Winery, Parnell Tower and Road America. A short drive to Plymouth, Fond du Lac, West Bend and Sheboygan. A wheelchair friendly property.

River Ridge-HOT TUB, Games, Luxury-10 bed, 5 STARS

The search is over, you have found the PERFECT getaway at River Ridge South! The moment you pull in, you will become instant hero for planning the ultimate retreat. This property has something for everyone! Beautiful seclusive country home (3800 sq ft) on 4 acres of a pristine and manicured lawn with the Onion River passing through it. This home is THE perfect countryside retreat for large group gatherings with three levels of finished space and great outdoor amenities.

Urban Townhouse

Enjoy Sheboygan in this beautifully renovated, 3 bedroom town house with a chic, mid-century vibe. Drink your morning coffee on a private outdoor deck or sleep in late on a plush queen sized bed. The homes lovely tile and wood floors, glass railing, and free Netflix are just some of the features you'll love. Free off street parking is included. Only a 10 minute drive to the American Club in Kohler and a 10-15 minute walk to downtown attractions and Lake Michigan beaches.