Holiday rentals with a hot tub in Sheboygan County

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Top-rated rentals with a hot tub in Sheboygan County

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Top guest favourite

Place to stay in Elkhart Lake

4.99 out of 5 average rating, 135 reviews

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.

Guest favourite

Home in Elkhart Lake

4.91 out of 5 average rating, 251 reviews

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

Top guest favourite

Home in Plymouth

5 out of 5 average rating, 70 reviews

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!

Home in Plymouth

5 out of 5 average rating, 5 reviews

Gorgeous private home in the woods BONUS Hot Tub

NEW FOR 2025…. 7 person hot tub added to a renovated front deck! Find it relaxing & private in this amazing home tucked away in the woods with big bay windows & plenty of wildlife. Enjoy the open floor concept & gas fireplace. Large rec room with pool table & foozball. Large deck with a beautiful out door table & chairs. Perfect for grilling & relaxing. Large kitchen as well. Minutes from Road America & 15 minutes to Whistling Straights, minutes to downtown Plymouth & easy access to Hwy 23.

Home in Plymouth

4.88 out of 5 average rating, 8 reviews

Sleeps 10+, close to Road America, golf and spas!

Property is located MINUTES from Kohler, Elkhart Lake, Road America. 1 hr to Milwakee! Main level of the property has a bedroom with walk in shower attached, spacious living room with gas fireplace, formal dining room, eat in kitchen with all the tools you need plus an office. Second floor has 3 bdrms & a full bath. The LL has the lounge, work out rm, 3rd ba and 5th bdrm. Enjoy the private high top deck or the lower patio! Great green space outside and parking for 5+ vehicles! Location!!!

Top guest favourite

Cabin in Cascade

5 out of 5 average rating, 165 reviews

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!

Flat in Sheboygan

4.84 out of 5 average rating, 31 reviews

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.

Top guest favourite

Apartment in Elkhart Lake

5 out of 5 average rating, 19 reviews

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!

Top guest favourite

Home in Sheboygan

4.98 out of 5 average rating, 211 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Enjoy this beautifully boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom with King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Sonos audio throughout. This beautiful boutique home is sure to impress!

Guest favourite

Apartment in Elkhart Lake

5 out of 5 average rating, 16 reviews

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.

Home in Sheboygan Falls

4.93 out of 5 average rating, 14 reviews

River Meadow Getaway in Sheboygan Falls

Welcome! Whether for work, pleasure, or something in between, please come and enjoy our country setting with city convenience. Relax at a campfire and take in the view. Walk or bike downtown for shopping and dining. Feeling adventurous? Explore the Sheboygan River meadow beyond our back yard, or kayak the gentle rapids. Excellent golf, spas, arts, and racing are within 15 minutes. Both at home and around town, we think you'll love your stay. —Ed and Amanda

Guest favourite

Home in Plymouth

4.98 out of 5 average rating, 42 reviews

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.