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!

Location

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.

Location · Family · Outdoor spaces

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

Racers Haven - 1 min from Road America

Treat yourself and enjoy the convenience of a single-family residence just 1/2 mile from the main gate of Road America. No traffic, no hassles, just racing! This 5-bedroom, 3400 square foot home, offers plenty of space to relax after a long day at the track. Enjoy either of the 2 games rooms or relax around the fire pit listening to the sounds of Road America. You'll also enjoy access to the oversized 2 car attached garage. Read the reviews and you'll know this is the place for your stay.

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.

Escape from the Track - Massage Chair | Fire Pit!

🏁 Escape the Track & Relax in Style! Just minutes from Elkhart Lake, this spacious Plymouth retreat is perfect for race weekends, family getaways, and group trips. Featuring 3 bedrooms, 2 baths, massage chair, Kohler bathroom with soaking tub, huge fully equipped kitchen, fire pit, multiple TVs, 2 stand-up arcade games, and a classic Nintendo system. Plenty of room for everyone to unwind after a day of adventure while enjoying all the attractions Plymouth and Elkhart Lake have to offer!

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

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.

De' Udder Place on the Water

****IMPORTANT**** The price you see upfront, NOW INCLUDES AIRBNB'S SERVICE FEES (As of August 2026) Lower level of my home on the water. Just 5 miles from Road America and 19 miles from Whistling Straits. Close to Kohler, Elkhart Lake, Lake Michigan, and the Kettle Moraine State Forest. After a day out in Sheboygan County, return to your guest suite and enjoy a cocktail in your private sunroom or in an Adirondack chair at the water's edge.

Road America Oasis: 25 Acres, Hot Tub & Orchard

Race weekend retreat on 25 quiet acres — soak under the stars in the hot tub, cook for the crew in a chef's kitchen, and unwind by the fireplace. 15 min from Road America and Elkhart Lake. Hot tub, fire pit, walking trails, apple orchard, in-home gym, and 3-season sunroom in the woods. 4BR/2.5BA luxury villa sleeps 8. Quiet, private, and built for relaxation — perfect for race teams, race fans, and groups looking for a luxurious summer getaway.

Blueberry Hill | Entire Home in Plymouth

Entire Home in Plymouth - this charming getaway offers the perfect balance of convenience and tranquility. Surrounded by rolling countryside views, spend your mornings sipping coffee on the screened-in porch, enjoy afternoons exploring the area's lakes, shops, and restaurants, and gather around the fire pit in the evening. This inviting 4-bedroom, 2-bath home offers comfortable living spaces designed for relaxation and togetherness.

Family · Kitchen · Indoor spaces