House holiday rentals in Elkhart Lake

The 2400 sq ft Plymouth Paddock near Road America!

This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

Location · Family · Checkout

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

Family · Location · Backyard

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

Value · Family · Decor

Spacious lower level priv entrance no cleaning fee

Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen includes refrigerator, microwave, keurig coffee maker, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

Value · Family · Cleanliness

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

Location · Family · Comfort

LUXE Manor With Modern, Elegant Vibes - 4,500 Sq

Modern chic blends with classic sophistication in this late 1800s Historic Manor, The Herman Hayssen House. Enjoy 4,500 sq ft of elegance and character that adorns this well-appointed home. Complete with 4 bedrooms, 3 full baths, and 1 half bath, many different areas for entertaining, both inside and out. The neighborhood is of the most elite in Sheboygan, situated between the lakefront and downtown and is a short drive to Whistling Straights and within an hour of Milwaukee and Green Bay.

Value · Family · Amenities

The Finish Line

Our cozy refurbished Cape Cod getaway is just steps from the downtown action, but offers a quiet respite at the end of the day. Enjoy the comfortable beds, fully appointed kitchen, fireplace, BBQ grill, onsite parking, outdoor patio, and big back yard. Walk to downtown restaurants and attractions, the Osthoff Resort, the Throttlestop, and beautiful Elkhart Lake, all just blocks away. About one hour from Lambeau Field, Milwaukee, or EAA. The Finish Line is your home away from home.

Location · Kitchen · Comfort

Lake House-Kayaks/Paddle Boards/Private Pier

🛶 Private Pier + Kayaks, Paddle Boards, & Lily Pad Raft 🏖️ Direct Lake Access with Crystal Clear Water ✨ Fully Renovated (2025) 🛏️ 4 Bedrooms with Premium Mattresses & Hotel-Quality Linens 🚿 2.5 Modern Bathrooms + Laundry Room 🍳 Chef-Friendly Kitchen with High-End Appliances ❄️ Central A/C, Fast WiFi, and Ample Parking 🏁 5 Mins to Road America | 20 Mins to Kohler Golf & Spa 🧭 Under 1 Hour to Milwaukee & Green Bay Attractions 🛟 Life Jackets & Water Toys Provided

Family · Location · Accuracy

Oak Haven | Theater • Game Room • Sauna • Firepit

Welcome to Oak Haven, a private 4,300 sq ft retreat surrounded by oak trees and peaceful Wisconsin beauty. 🌿 • 12-seat movie theater with plush recliners & surround sound 🎬 • Game room with pool, ping pong, shuffleboard & poker 🎱 • Infrared sauna + two outdoor fire spots for perfect nights 🔥 • Gourmet kitchen & dining for twelve 🍽️ • Minutes to Kohler golf, Kettle Moraine & Road America 🏎️ ✨ Oak Haven—where relaxation, laughter, and connection come naturally.

Value · Family · Pool

The Suncatcher -Steps from Lake - Fenced Yard

Welcome to the Suncatcher. Our cozy and bright Midwest retreat just a block away from Lake Michigan . Step into our lovingly remodeled 1930's home where modern comfort meets timeless charm. As you enter you will be greeted by the inviting warmth of exposed brick walls and abundance of natural light that fill every corner. With three bedrooms and two bathrooms, our spacious retreat is perfect for families, friends, or golf enthusiasts seeking a relaxing getaway.

Location · Family · Hospitality

Outdoor Sauna | 6-BRs | Kohler-Andrae

🏖️ Private Sandy Beach on Lake Michigan 🔥 Waterfront Fire Pit for Cozy Evenings 🧖‍♀️ New Lakeview Sauna 🪟 Open-Concept Living with Wall-to-Wall Lake Views 🛏️ 6 Bedrooms – Sleeps Large Groups Comfortably 🍳 Fully Equipped Kitchen & Spacious Dining Area ☀️ Expansive Deck for Coffee, Sun & Scenic Relaxation 🌲 Wooded, Tranquil Neighborhood Near Kohler-Andrae State Park 🚗 Minutes to Sheboygan, Kohler, & Road America 🔐 Private Home with Seamless Self Check-In

Location · Family · Parks

Lake Views | Walk Everywhere | 3BR Beach Resort

Stay Together at Elkhart Lake Beach Resort | 3BR Lakeview Condo for Couples & Friends Skip the split hotel rooms—this rare 3-bedroom, 3-bath condo at the Elkhart Lake Beach Resort is designed for groups who want to actually spend time together. Perfect for 2–3 couples or a small group of friends, you’ll have a true shared living space plus full access to one of Elkhart Lake’s most social, walkable resort experiences.

Location · Family · Parks