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, 207 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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Superhost

The A-frame cabin is framed by lush greenery and colorful landscaping. A welcoming pathway leads to the entrance, featuring a spacious deck. The cabin's dark exterior contrasts with the surrounding trees, creating a serene and private atmosphere.

Cabin in Elkhart Lake

4.99 out of 5 average rating, 363 reviews

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, 54 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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4.94 out of 5 average rating, 34 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

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.

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Superhost

5.0 out of 5 average rating, 4 reviews

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!

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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, 17 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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4.95 out of 5 average rating, 177 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.

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4.98 out of 5 average rating, 54 reviews

Villa in Plymouth

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.

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Superhost

5.0 out of 5 average rating, 4 reviews

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.

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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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5.0 out of 5 average rating, 38 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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4.97 out of 5 average rating, 101 reviews

A large log cabin is set amidst golden cornfields, with vibrant autumn foliage surrounding the property. The structure features a stone chimney and multiple windows, inviting natural light. The expansive lawn includes a seating area facing the fields, creating a peaceful outdoor retreat.

Cabin in Plymouth

1-Mile to Road America, 2-Miles to Elkhart Lake

🏕️ Massive Log Cabin on 5 Private Acres 🛌 Sleeps 18 | 7 Bedrooms | 3 Bathrooms 👨‍🍳 Fully Loaded Kitchen + Group Dining Area 📺 Cozy Living Room with Large Smart TV 🌲 Spacious Deck with Grill & Nature Views 🏁 1 Mile to Road America Raceway 🏖️ 2 Miles to Elkhart Lake Beach at Fireman’s Park 🔥 Perfect for Reunions, Race Weekends & Retreats 🐾 Pet-Friendly Cabin ($55/night per dog, with notice)

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Popular amenities for Plymouth holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Plymouth

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, 19 reviews

Racers Haven - 1 min from Road America

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A welcoming living area features large windows overlooking the lake, allowing natural light to fill the space. A brick fireplace is highlighted against a wall adorned with décor. Comfortable seating is arranged around a decorative table, creating an inviting atmosphere.

4.88 out of 5 average rating, 58 reviews

Lake Front Cottage With Dock. Walk to Road America

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5.0 out of 5 average rating, 33 reviews

A modern three-story house is depicted, featuring large windows and an expansive deck surrounded by lush greenery. The structure presents a sleek design with a stone facade and a spacious garage area visible. Outdoor seating is arranged on the deck, promoting a relaxed atmosphere.

Home in Rhine

JAmbers Road America Track House

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A charming white house is seen nestled among lush green trees and colorful foliage. A well-manicured lawn leads up to the front porch, which features a dark roof and an inviting entryway. A white picket fence outlines the property, enhancing its quaint appeal.

5.0 out of 5 average rating, 31 reviews

Riverside House

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5.0 out of 5 average rating, 14 reviews

Vibrant Victorian

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A simple entrance is highlighted by a white door adorned with a small window, framed by green siding. A festive decoration, resembling a snowman, composed of evergreen branches and a golden hat, is positioned beside the door, adding a cheerful touch.

Apartment in Plymouth

4.64 out of 5 average rating, 371 reviews

Pineyard Plymouth Apartment

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A charming home is set within a wooded landscape, featuring a spacious front deck and a two-car garage. Large windows allow natural light to fill the entryway. An inviting outdoor seating area is visible, surrounded by trees, ensuring privacy and a serene atmosphere.

5.0 out of 5 average rating, 9 reviews

Stunning private home in the woods BONUS Hot Tub

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A living area is presented with two dark blue sofas, each featuring accent pillows in a complementary pattern. A soft area rug in shades of blue and gray lies beneath a small wooden table, with natural light filtering through the three windows.