Holiday houses in Plymouth

The kitchen features dark cabinetry with artistic landscape designs and a large white countertop island. Stainless steel appliances include a stove and dishwasher, while a coffee maker is positioned on the counter. Natural light enters through a nearby doorway, illuminating the warm wood tones of the floor.

4.97 out of 5 average rating, 211 reviews

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!

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4.99 out of 5 average rating, 367 reviews

Cabin in Elkhart Lake

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.

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5.0 out of 5 average rating, 58 reviews

A spacious living area is observed, featuring a comfortable gray sofa and a coffee table resting on a light rug. Bright windows allow natural light to illuminate the room. A television is positioned on a media console, along with a small dining table and chair set against the wall.

Guest suite in Plymouth

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

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4.96 out of 5 average rating, 184 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

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.

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A sunlit sunroom features a cozy seating arrangement with two wicker armchairs and a spacious sofa adorned with blue and white cushions. Large windows provide multiple views of the surrounding greenery and the lake, allowing natural light to fill the space.

5.0 out of 5 average rating, 19 reviews

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

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4.96 out of 5 average rating, 179 reviews

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.

ValueFamilyCheck-in

4.83 out of 5 average rating, 124 reviews

Two Adirondack chairs are positioned along the water's edge, surrounded by trees and greenery. A tree-mounted birdhouse is visible nearby. The scene reflects a tranquil setting by the blue waters, enhancing the natural surroundings.

Guest suite in Plymouth

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.

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5.0 out of 5 average rating, 12 reviews

3 Minutes to Road America | Amazing Location!

• Patio with Fire Pit, Grill, & Bar Gazebo • Deck with Outdoor Dining • Indoor Bar to unwind & entertain • 65” Smart TVs in both living areas • Fresh Renovations: Modern finishes, stylish decor, and all-new furnishings Clean and newly renovated 5-bedroom, 2.5-bath home. Plenty of space for race weekends, group getaways, or golf trips! Relax outside on the deck, fire up the grill, or unwind indoors with all the comforts of home.

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4.89 out of 5 average rating, 27 reviews

Walk to Road America-Private w/Fire Pit+Loft+Views

The Hillside Cottage is located just steps from Road America. It offers one of the few walkable stays to the track while still feeling peaceful and private. The cottage is also perfectly positioned for golf, hiking, lake days, and exploring the charm of Elkhart Lake and the surrounding areas. Enjoy sunrise coffee on the wrap-around deck, evenings by the firepit, and plenty of space to gather, unwind, and make memories.

FamilyLocationIndoor spaces

5.0 out of 5 average rating, 40 reviews

An open living space is shown, featuring a spacious sectional sofa in a neutral tone. A coffee table sits centrally, with a large rug underneath. The kitchen area is visible, equipped with dark cabinetry and dining seating. Natural light fills the room through large windows.

Townhouse in Plymouth

Townhouse walking distance to Road America

Welcome to our beautiful 3-bedroom, 2-bath townhouse, just a short walk to the Main Gate at Road America! This open-concept home features a spacious king primary suite with a walk-in shower and closet, a queen bedroom, and a third bedroom with two twin beds plus a twin trundle. Enjoy main-floor laundry, a private patio with views of the Main Gate, and the perfect location for race weekends or an Elkhart Lake getaway.

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5.0 out of 5 average rating, 19 reviews

Townhouse in Plymouth

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.

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The exterior of a two-story house is showcased, featuring a light-colored facade and a spacious deck. The driveway is bordered by vibrant purple flowers and lush greenery, contributing to the welcoming atmosphere. A garage is visible, enhancing the home's functionality.

4.92 out of 5 average rating, 50 reviews

Kettle Breeze

Located in the middle of the Kettle Moraine State Forest, you will find an endless amount of activities around while staying at our 3 bedroom, 2 bathroom house. Centrally located whether you are looking to visit Lake Michigan, Elkhart Lake's Road America, hiking trails or just looking for a peaceful place to stay while you enjoy all that Sheboygan County has to offer!

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Popular amenities for Plymouth holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Plymouth

5.0 out of 5 average rating, 6 reviews

Escape from the Track - Massage Chair | Fire Pit!

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4.94 out of 5 average rating, 33 reviews

Turn 15 Lodge near Road America

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5.0 out of 5 average rating, 27 reviews

Family Home Near Road America & Downtown Plymouth

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A spacious gourmet kitchen features modern stainless-steel appliances and elegant granite countertops. Overhead, three woven pendant lights provide gentle illumination. An inviting kitchen island with seating for six offers a perfect spot for gathering, surrounded by ample cabinets and a view of natural light entering through nearby windows.

5.0 out of 5 average rating, 42 reviews

Farm Fresh Eggs, Amazing Outdoor Space w/ Fire Pit

LocationFamilyDecor

4.94 out of 5 average rating, 36 reviews

A deck furnished with wooden chairs offers a view of the reflective lake surrounded by vibrant autumn foliage. Colorful trees frame the water, enhancing the natural setting. Tables and seating are visible in the open space below, providing areas for gathering.

Cabin in Plymouth

Walking distance to Road America, Lakefront

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A spacious living area features a stone fireplace beneath a wall-mounted TV. A wooden coffee table is positioned on a dark hardwood floor, with a cozy red throw draped over a light-toned couch. Soft lighting is provided by track lights on the ceiling.

5.0 out of 5 average rating, 20 reviews

Racers Haven - 1 min from Road America

LocationComfortCleanliness

4.99 out of 5 average rating, 111 reviews

A charming bungalow is framed by a large tree with purple leaves, featuring a neatly maintained lawn and bordered by low shrubs. The entrance is welcoming, with a pathway leading to the front door, and an inviting porch area is visible.

Home in Sheboygan Falls

Adorable bungalow in historic Sheboygan Falls,WI

LocationFamilyBackyard