Holiday houses in Plymouth

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!

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Downtown Plymouth, WI Second Floor 2 Bed Apartment

Second floor apt. with two single bedrooms, a queen bed and a full bed in the other. Full bath, kitchen, living room, outdoor smoke deck, long driveway for parking (first 3 feet of the driveway are steep). Enjoy a short walk to many shops and restaurants or check out the wall murals in the Cheese Capital of the World! You don’t have to travel too far for excitement Road America (4.5 mi), Plymouth Dirt Track (1.1 mi), Whistling Straits Golf Course (20.5 mi) Kettle Moraine nature trails 20.4 mi

The Loft at Hickory Haven-A Modern Rural Studio

The Loft at Hickory Haven is a modern country retreat made for two! Mary & Bob constructed The Loft studio in 2020 and filled it with the modern traveler's amenity wish list: A comfy king bed, central AC, a gas-fired stove, a modern bathroom, and a kitchenette with dining area. The property's rural setting offers a peaceful haven from your daily grind. Your day will start with the chirping of birds or a wild turkey sighting and end with a star-filled sky that is a site to behold! Welcome!

Walking distance to Road America, Lakefront

Nestled in the woods, you will find fun for the whole family. Our Little Elkhart lakefront cottage has two bedrooms that can easily sleep six guest. We offer kayacking, biking, swimming, an outdoor fire pit, two decks overlooking the lake, and highspeed internet service. This cottage sits on 3/4 acres less than 1 mile from Road America, 4 miles from downtown Elkhart Lake, and several beautiful golf courses. It has all of the amenities for your memorable family vacation. Sorry no pets.

hot tub and sauna on 5 private acres

Looking for 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 getaway awaits!

Secluded Elkhart Retreat | Pool, Hot Tub & Sunset

Nestled just minutes from Downtown Elkhart Lake, this custom-built cordwood home offers a secluded sanctuary experience. Perched atop a hill, the unique 16-sided house provides breathtaking views of the state forest and surrounding farmland. Despite its remote feel, you’re only a 5-minute drive from the charming Elkhart Lake business district. Day hikes on the ice age trail are just steps away from the home. Tap the ❤️ to save this listing!

Lake Front Cottage With Dock. Walk to Road America

Do you like tranquil, peaceful and serene? Don’t miss out on our lake front house. Huge windows with lake views and lots of natural light. Walking distance to Road America. Relax by our outdoor fire pit. Fish or kayak off or dock or swim within 900 ft of the driveway. Enjoy our game room with Pac-man video console or play corn hole. Quiet and relaxing but minutes to the Kettle trails and Historic downtown Elkhart Lake.

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Winner's Circle | Luxury Stay Near Road America

The Winner’s Circle Townhouse is a luxury retreat perfectly located just steps from Road America and minutes from Elkhart Lake and Plymouth. Designed for comfort and entertaining, this spacious townhouse offers upscale amenities, generous living areas, and a rare heated and cooled 4-car garage—making it an ideal stay for race weekends, group getaways, or relaxing escapes.

Crystal Sunset Loft - Elkhart Lake

Beautiful views, beautiful space – Crystal Sunset Loft is THE place to relax if you are looking for a quiet and scenic refuge after a day at the track or hiking through the kettles. Only a mile away from Road America’s main gate, Elkhart Lake, and the village’s fun nightclub scene, this is the perfect setting for your weekend or mid-week getaway.