Become a host

Vacation rentals in Plymouth

Find and book unique accommodations on Airbnb

Quick stats about vacation rentals in Plymouth

  • Total vacation rentals

    Explore 50 vacation rentals in Plymouth

  • Nightly prices starting at

    Plymouth vacation rentals start at ﺩ.ﺇ 220 per night before taxes and fees

  • Verified guest reviews

    Over 2,860 verified reviews to help you choose

  • Family-friendly vacation rentals

    40 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wi-Fi availability

    50 of Plymouth vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Plymouth rentals

  • 4.9 Average rating

    Plymouth stays are highly rated by guests—averaging 4.9 out of 5!

Top-rated vacation rentals in Plymouth

Guests agree: these stays are highly rated for location, cleanliness, and more.

1 of 1 pages1 / 1
Top guest favorite
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.
Home 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!

4.97 out of 5 average rating, 211 reviews
Top guest favorite
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.

4.99 out of 5 average rating, 367 reviews
Top guest favorite
A rustic modern home is showcased, featuring a spacious wraparound deck surrounded by lush greenery. An inviting hot tub glistens in the sun, and an arcade room with various games is displayed, offering entertainment options for guests.
Home in Elkhart Lake

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

4.93 out of 5 average rating, 301 reviews
Top guest favorite
A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.
Home in Sheboygan

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

4.96 out of 5 average rating, 128 reviews
Top guest favorite
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

5.0 out of 5 average rating, 58 reviews
Top guest favorite
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.

4.96 out of 5 average rating, 185 reviews
Top guest favorite
Cabin in Cascade

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!

5.0 out of 5 average rating, 287 reviews
Guest favorite
The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.
Cottage in Random Lake

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

4.85 out of 5 average rating, 121 reviews
Guest favorite
Home in Plymouth

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.

4.96 out of 5 average rating, 179 reviews
Top guest favorite
A serene outdoor setting features a stone fire pit surrounded by wooden benches. The custom-built home, with large windows, is visible in the background. Soft twilight hues illuminate the peaceful landscape, complemented by trees lining the property.
Earthen home in Elkhart Lake

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!

4.98 out of 5 average rating, 162 reviews
Top guest favorite
A quaint living space features an antique-style fireplace made of dark wood, with a circular mirror above it. A flat-screen television is mounted on the wall opposite a small table and a suitcase rests on the hardwood floor, accompanied by a decorative flower arrangement.
Apartment in Waldo

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.

4.98 out of 5 average rating, 324 reviews
Guest favorite
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.

5.0 out of 5 average rating, 40 reviews

Popular amenities for Plymouth vacation rentals

GymBBQ grillLaptop-friendly workspaceWifiAir conditioning

Other great vacation rentals in Plymouth

Top guest favorite
Home in Plymouth

Turn 15 Lodge near Road America

4.94 out of 5 average rating, 33 reviews
Guest favorite
Home in Plymouth

3 Minutes to Road America | Amazing Location!

5.0 out of 5 average rating, 12 reviews
Guest favorite
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

4.94 out of 5 average rating, 36 reviews
Top guest favorite
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.
Home in Plymouth

Lake House-Kayaks/Paddle Boards/Private Pier

5.0 out of 5 average rating, 19 reviews
Top guest favorite
Home in Plymouth

Family Home Near Road America & Downtown Plymouth

5.0 out of 5 average rating, 27 reviews
Top guest favorite
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.
Home in Plymouth

Racers Haven - 1 min from Road America

5.0 out of 5 average rating, 20 reviews
Top guest favorite
Apartment in Sheboygan

Clean, Comfy Stay Near Parks, Downtown & Lake!

5.0 out of 5 average rating, 63 reviews
Top guest favorite
Home in Cleveland

Shoreline Serenity

5.0 out of 5 average rating, 20 reviews

When is the best time to visit Plymouth?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 459ﺩ.ﺇ 463ﺩ.ﺇ 643ﺩ.ﺇ 687ﺩ.ﺇ 690ﺩ.ﺇ 881ﺩ.ﺇ 683ﺩ.ﺇ 602ﺩ.ﺇ 643ﺩ.ﺇ 584ﺩ.ﺇ 441ﺩ.ﺇ 459
Avg. temp-8°C-6°C0°C7°C14°C19°C21°C20°C16°C9°C2°C-4°C

Frequently Asked Questions

  • Are there family-friendly house rentals in Plymouth?

    Plymouth has more than 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Plymouth?

    Experience the best of Plymouth with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Plymouth?

    Four-legged friends are welcome in Plymouth. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there house rentals with a dedicated workspace in Plymouth?

    Yes! Work meets play with ease at over 20 house rentals in Plymouth featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do house rentals in Plymouth have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Plymouth have wifi?

    Absolutely! We offer over 40 house rentals with wifi in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Plymouth have a bbq area?

    Absolutely! We offer over 20 house rentals with a bbq area in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Plymouth?

    Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 40 homes with air conditioning, over 40 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore