Holiday rentals with a hot tub in Sheboygan County

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Top-rated rentals with a hot tub in Sheboygan County

Guests agree: these rentals with a hot tub are highly rated for location, cleanliness and more.

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Guest favourite
A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.
Home in Elkhart Lake
4.92 out of 5 average rating, 274 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 Elkhart Lake
4.98 out of 5 average rating, 100 reviews

Fernwood Lodge Elkhart Lakehome: pier, kayaks, tub

Beautiful, serene lake home on pristine Elkhart Lake. The hot tub, deck, screen porch & stone patio all boast gorgeous lake views. Your private pier is perfect for a dip, paddling or lounging by the water, then bask 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🏳️‍🌈

Top guest favourite
Home in Plymouth
5 out of 5 average rating, 39 reviews

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 (6 beds - 1 King, 4 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.

Top guest favourite
Cabin in Oostburg
5 out of 5 average rating, 22 reviews

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!

Top guest favourite
Two black Adirondack chairs are positioned on a wooden deck overlooking a calm lake. A small side table sits between them, providing a perfect spot for refreshments. Lush greenery surrounds the lake, reflecting the serene landscape under a clear blue sky.
Home in Plymouth
5 out of 5 average rating, 71 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!

Top guest favourite
An inviting wellness space features a hot tub with gentle bubbles and soft green lighting. Adjacent, a wooden dry sauna awaits, surrounded by potted plants. Comfortable seating with decorative pillows is arranged nearby, creating a serene atmosphere for relaxation.
Home in Sheboygan
4.98 out of 5 average rating, 256 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/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. Let us impress you and help make it a memory.

Top guest favourite
Home in Elkhart Lake
4.99 out of 5 average rating, 140 reviews

Schoolhouse Straight Inn-Hot Tub- Suana - plunge

Welcome back to school! This rustic remodel of 1925 schoolhouse has two full apartments, rented together. 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
A spacious studio condo is showcased with two queen beds, a cozy sitting area, and a fully equipped kitchenette. A flat-screen TV is mounted on the wall, while a high-top table for two is featured in the background, providing a functional living space.
Apartment in Elkhart Lake
5 out of 5 average rating, 19 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.

Top guest favourite
Cabin in Cascade
5 out of 5 average rating, 227 reviews

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.

Top guest favourite
Home in Plymouth
4.95 out of 5 average rating, 44 reviews

Craftsman Retreat Near Road America-Hot Tub & Pool

Private Craftsman home in Plymouth, WI—just 4 miles from Road America. Ideal for race teams and families, this two-story home offers 4 bedrooms, 2 baths, a private outdoor hot tub, and a seasonal inground pool (summer–mid-September). Free on-street parking plus a garage and shared driveway provide convenient vehicle access. Located in a quiet neighborhood near grocery stores, dining, and local attractions. No pets. Longer stays (7+ nights) by request.

Home in Oostburg
4.51 out of 5 average rating, 37 reviews

Awesome Game Room-XL Beachfront HM-Pool Table, ETC

Located at the very end of a beautiful private road, the Sand Castle Beach House is nestled between beautiful Lake Michigan shoreline and a gorgeous forest. The 3 acre private and exclusive lot features an expansive lake side yard that is level and ready for outdoor games. 2 grills on the large lakeside deck are ready for your vacation time. Laze in the chaise loungers or Adirondack chairs and listen to the waves lap the shoreline.

Guest favourite
A two-story home is seen with gray siding and brown shutters, featuring a covered front porch supported by wooden columns. Lush green shrubs and flower beds line the walkway, while a well-maintained lawn extends around the property. A car is parked in the driveway.
Home in Random Lake
4.94 out of 5 average rating, 65 reviews

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.

Popular amenities for rentals with a hot tub in Sheboygan County