Vacation Home Rentals By Owner In Plymouth, WI

Showing 36 Of 36 Vacation Rentals

$522.87

Hot Tub, Kayaks, SUP's & Firepit

Plymouth, Wisconsin, United States

Panoramic Gold Coast Sunsets from Hilltop Windowsbr Private Hot Tub on Spacious Lakeview Deckbr Kayaks & SUP Boards Included for Crystal Lake Funbr Cozy Lakeside Firepit for Evenings Under the Starsbr ️ Multiple Living Rooms + Sleeper Sofa for Extra Spacebr ️ Premium Beds & Linens for Restful Nightsbr Fully Equipped Kitchen for Home-Cooked Mealsbr Close to Hiking Trails, Dining & Sheboygan AttractionsbrbrWhy Golden Hour Getaway brbrFrom the moment you step inside, you’re greeted by a wall of expansive windows framing panoramic views that stretch across the lake and beyond. Imagine sipping your morning coffee or unwinding in the evening with a glass of wine as the sun slowly dips below the horizon — this is lakeside living elevated to an art form.brbrRelax & Recharge:brSink into the warm waters of your private hot tub on the expansive deck, perfectly positioned to capture unobstructed sunset vistas. The deck offers ample seating for lounging, dining, or simply soaking in the serene beauty that surrounds you.brbrModern Comforts & Thoughtful Touches:brInside, you’ll find a harmonious blend of cozy and contemporary — from plush furnishings to a fully equipped kitchen ready for your culinary creations. Whether it’s a romantic getaway, a family retreat, or a peaceful solo escape, Golden Hour Getaway offers the perfect backdrop for making memories.brbrWhat You’ll Love:brbrStunning hilltop location with Gold Coast sunsets every nightbrWall of windows flooding the home with natural light and lake viewsbrPrivate hot tub on a spacious deck overlooking Crystal LakebrOpen-concept living area perfect for relaxing and entertainingbrComfortable bedrooms with premium linens for restful nightsbrConvenient access to local dining, hiking, and water activitiesbrMultiple living rooms to get away for a bit. Lower-level living room includes a sleeper sofa.brbrExplore & Experience:brBeyond the house, explore the charming towns of Sheboygan County, like nearby Elkhart Lake, or check out our local wineries, trails, and beaches. brWhether you’re seeking adventure or relaxation, Golden Hour Getaway puts you right where the best of Wisconsin’s lake life meets the comforts of home.brbrBook now and make your next escape a luminous experience — where every sunset promises a golden hour worth savoring.brbr* The hottub is an amenity and while we will make every effort to insure a working and properly heated hot tub experience, this cannot be guaranteed. Therefore, we cannot offer cancellation or discounts should the hot tub or any other amenity not be in perfect working order.brbr- Guests are required to sign a rental agreement and set up a deposit for all stays.br- Dock is NOT suitable for tying off a boat.br- Outdoor amenities like Dock/Kayaks/Standup Paddle Boards/Firepit may not be available in the Fall/Winter/Spring past October 10th or prior to May 21st seasonally. Please inquire.

Bed

Bath

Sleeps

Exceptional(5)

$663.91

/ Nightly

Private Vacation Home

Plymouth Gem: Spacious Home with Bar, Game Room & Yard Near Road America

Plymouth, Wisconsin, United States

Welcome to your home away from home in charming Plymouth, Wisconsin. Just minutes from Road America, this spacious 4-bedroom, 4.5-bathroom home combines cozy charm with modern amenities—perfect for families, race fans, and group getaways alike.brbrPlease Note: At this time, we are only accepting reservations for stays of 7 nights or less. We appreciate your understanding and look forward to hosting you!brbr**Highlights of the Home:**brbr- **Room for Everyone** br - 4 bedrooms: 3 with queen beds, 1 with a full bed br - Private office with a pull-out couch bed br - Two pull-out sleeper sofas in the finished basement br - Sleeps up to 12 guests comfortably brbr- **Indoor and Outdoor Comfort** br - Indoor gas fireplace and outdoor fire pit br - Large smart TVs throughout the home br - Dart board, board games, and lawn games (Kan Jam, cornhole, more to come) br - Washer and dryer available for guest use brbr- **Entertainment Features** br - Record player and multiple speakers throughout the home br - Finished basement with lounge area, dart board, and kitchenette br - Basement kitchenette includes a wine/beverage fridge and bar brbr- **Spacious Master Suite** br - Master bedroom features a large en-suite bathroom br - Oversized walk-in shower and separate jacuzzi tub brbr- **Fully Equipped Kitchen & Dining** br - Kitchen includes all essentials, plus a Keurig coffee maker br - Refrigerator with built-in filtered water dispenser br - Formal and informal dining rooms for meals and gatherings brbr- **Outdoor Space & Amenities** br - Large open yard and back deck br - Gas grill with direct hookup to the house’s gas line br - Full garage and spacious driveway with ample parking brbr- **Work-Friendly Amenities** br - High-speed WiFi throughout the home br - Private office for remote work or quiet reading brbr- **Additional Features** br - Large windows throughout the home, offering plenty of natural light br - Spacious mudroom/laundry room next to the garage entrance br - Security system for peace of mind brbr- **Nearby Attractions & Location** br - 5 mins to Road America br - 10–15 mins to Elkhart Lake (shops, dining, lake access) br - 25 mins to Kohler / Sheboygan (Lake Michigan beaches, spas, dining) br - Local grocery stores and gas stations within 5-10 minutes br - Quiet, safe neighborhood – great for evening walks or yard games brbr- **Additional Notes** br - No pets allowed br - Located in Plymouth, Wisconsin, just minutes from Road America brbrWhether you're planning a weekend with friends, a family vacation, or a stay for one of Road America’s many events, this home is your perfect launch point for comfort, convenience, and good times. Book your stay today and make lasting memories in Plymouth.

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Sleeps

Exceptional(38)

$702.32

/ Nightly

Private Vacation Home

Road America Adjacent Lake House with indoor pool

Plymouth, Wisconsin, United States

Road America adjacent four bedroom house on Little Elkhart Lake with indoor pool and spacious deck overlooking Little Elkhart Lake with gazebo.brPrivate dock with three kayaks and rowboat.brTwo minutes from Road America's gate six.brLess than ten minutes to downtown Elkhart Lake, eight minutes to downtown Plymouth.

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Bath

Sleeps

Exceptional(2)

$809.63

/ Nightly

Private Vacation Home

The 2,400 sq. ft. Plymouth Paddock near Road America, 4 bedrooms, 2.5 bathrooms

Plymouth, Wisconsin, United States

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. brbrThe main level is home to the kitchen, dining room, living room, laundry room with washer and dryer, a queen bedroom, and a full bathroom with a shower. Upstairs is home to a full bathroom with a tub/shower combination and three bedrooms. The first bedroom has two queen sized beds, the second bedroom has two twin beds, and the third bedroom has a king sized bed and an en-suite half bath that is private to the king bedroom. brbrWelcome to your home away from home!

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$1017.33

/ Nightly

Private Vacation Home

Lake home with crystal clear water

Plymouth, Wisconsin, United States

Come enjoy the pristine waters of Crystal Lake. Relax: Sip coffee or cocktails on our two large decks with sweeping lake views. Get active: swim, paddle board, or kayak on one of Wisconsin’s most coveted lakes. Explore: experience top-knotch recreation for the whole family to enjoy.brbr25 minutes to Whistling Straights (future site of the 2021 RYDER CUP)br4 minutes to world-class Road Americabr6 minutes to Elkhart Lakebr21 minutes to Kohlerbr26 minutes to Sheboygan and Lake MichiganbrbrWe have wireless internet and a large screen TV in living room with access to all streaming services with your own accounts. We have two stand up paddle boards for guests to use as well as a large swimming mat. We have also have two youth kayaks and plenty of life jackets.brbrOne of the bedrooms upstairs with queen bed has air conditioning, but the rest of the home does not. There are plenty of windows and several fans.

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Bath

Sleeps

Exceptional(47)

$487.06

/ Nightly

Private Vacation Home

One Minute to Road America - Close to PGA Golfing

Plymouth, Wisconsin, United States

Enjoy the activities at the Race track, and come back for relaxation. Plenty to do nearby as well. Osthoff Resort 6 minutes – American Club in Kohler 20 minutes - Whistling Straits (the 2020 Ryder Cup Golf Course) 35 Minutes. Enjoy the restaurants and shops of either Plymouth or Elkhart Lake (6 minutes away).brThe two decks offer an outstanding view of Little Elkhart Lake. Enjoy a paddle in the canoe, the fire pit, or the paddle board even a bike ride-all are available for your enjoyment.br

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Exceptional(13)

$755.54

/ Nightly

Private Vacation Home

4 bedroom, 3 Bath Home only 9 Minutes from Road America

Plymouth, Wisconsin, United States

Beautiful 4 bedroom, 3 bath home located on a quite dead end road only minutes from Road America, Kohler and PGA events at Whistling Straits. Home has 4 bedrooms, each with a queen bed. Luxurious amenities throughout the home including deluxe kitchen, master suite with whirlpool tub and over a half acre of wood backed yard. Back porch overlooks backyard with fire pit. Parking for 5 vehicles without difficulty.

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Sleeps

Exceptional(33)

$983.67

/ Nightly

Private Vacation Home

Luxurious Newly Renovated 4 Bedroom Home Near Elkhart Lake, Green Bay & Kohler

Plymouth, Wisconsin, United States

Our beautiful, newly renovated home is your ultimate getaway retreat. This spacious house not only includes modern touches, but also comes with an amazing outdoor feel. The huge open concept kitchen/family room provides the ideal space for hanging out. Our home has a spacious backyard and large deck with an 8 person hot tub. Enjoy the recently remodeled gourmet kitchen with plenty of seating area for your friends and family. Some noteworthy house details include quartz countertops, custom cabinetry, gas fireplace, wet bar, Sonos sound system, and new Kohler fixtures throughout.brNewly renovated master bath and bedroom includes a gorgeous walk in shower and double sinks. We have a total of 6 beds and 4 bedrooms plus plenty of room for air mattresses throughout the 3 levels. It's a perfect getaway for family and friends.brbrAll linens, towels, toiletries are provided. Kitchen comes fully stocked with pots/pans, spices, etc. We also have coffee so pack light and make your travel plans hassle free!brbrRest easy with sleeping arrangements for 14+ (2 queen sized air mattresses are available). brbrGuest accessbrThe entire home is yours as well as the deck, hot tub and garage.brbrWe welcome kids. They will love to play in the hot tub. We also have a pretty amazing Lego collection.

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Bath

Sleeps

Exceptional(13)

$1002.25

/ Nightly

Private Vacation Home

House Neighboring Road America and the Mullet River

Plymouth, Wisconsin, United States

Modern farmhouse nestled on a dead end road a mile from Road America and about an hour from Lambeau Field for the 2025 NFL Draft. The house has an open concept, great for entertaining with a beautiful view overlooking the Mullet River. Main floor ensuite with double walk-in shower and laundry room. Lower level is a walk-out basement containing three bedrooms, one bathroom and a large family room.

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Exceptional(18)

$265.33

/ Nightly

Private Vacation Home

Wyatt's Country Home - King Bed!

Plymouth, Wisconsin, United States

Soak up the modern vintage charm of our fully remodeled and updated home! Thank you for choosing our sparkling clean space. Our home is nestled on two quiet acres just north of Plymouth in the peaceful country. Enjoy coffee as the sun rises from one of the two decks, or perhaps a cocktail by the fire as the sun sets. We ourselves lived in this home for our first 5 years and turned it into a beautiful and peaceful space for ourselves that we would now like to share with everyone.

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Exceptional(35)

$555.09

/ Nightly

Private Vacation Home

Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.

Plymouth, Wisconsin, United States

Beautifully appointed, third floor Townhouse at the Trackside Townhouses across the road from famous Road America. Short 20-minute drive to world-famous Whistling Straits Golf course.brYou will enjoy the relaxed decor of this recently built 2-bedroom unit. The master bedroom has a king bed, large walk-in closet, and en-suite bathroom with walk-in shower. The second bedroom has a queen bed with the 2nd full bathroom just down the hall. Luxury bedding and towels are provided. There is a washer and dryer in the unit for your convenience.brStep into a kitchen filled with all the cooking utensils and dishes you need to prepare a quick snack or full meal. New stove, microwave, dishwasher, and refrigerator. Just stop by the store on the way, and you're set!brEnjoy relaxing in the comfy living room area with a fire in the gas fireplace. Watch the large TV equipped with cable or use the high-speed internet to stream your favorite show. You can also sit on the third story deck overlooking Road America while listening to the roar of the engines. We have spared no expense on the furnishings and decor. brWe have free parking for up to 3 vehicles next to our building. Please note our unit is not handicapped accessible.brbrABOUT THE AREA:brElkhart Lake, less than five minutes away, has a small town feel with upscale amenities, and nearby Plymouth, the Cheese Capital of the World, is a full-service community with a cute downtown while also offering the stores you need for your basics. Between these two towns, you won’t run out of things to do and places to go! Antique shops, art galleries, boutiques, golf, restaurants, taverns, local breweries, farmer’s markets, festivals throughout the year…we have it all in this area! And, if you want to explore further, Kohler and Sheboygan are only a 20-minute drive away.brFoodies, and aren't we all, will enjoy many eating establishments in the area. It will be tough to choose which experience you want, from a drive-in burger to a quick bite at the beach to a traditional Wisconsin supper club meal to a gourmet entree. Don’t forget to try some cheese curds!brFor water lovers, Elkhart Lake is pristine with public beach access for a nominal fee. Rent water sport equipment from the local resorts.brGolfers will love the numerous golf courses in the area. Quit Qui Oc Golf Club is a five-minute drive from our unit, and Whistling Straits, host of the 2021 Ryder Cup, is just 20 minutes away.brAthletes will enjoy the great hiking and biking trails, including part of the Ice Age Trail, in the Kettle Moraine Forest that surrounds Elkhart Lake, not to mention the winding hills on our local low-traffic roads. Elkhart even hosts a triathlon every June. Road America also offers opportunities for you to get on the track. Check out their website for when you can run, walk, or bike around the racetrack certain evenings of the week. And if driving is more your style, then sign up for a sunset cruise, and get your own car on the track!brWhile summer in Wisconsin is glorious, fall is equally splendid. The rolling hills of the Kettle Moraine Forest provide fantastic winding drives, giving you one incredible view after the next of the gorgeous scenery. Stop and take a hike along the forest trails or check out local apple and pumpkin farms. And in the winter, you can take advantage of local ice-skating venues, cross country skiing trails, snow shoeing, and more. Elkhart even has a special festival dedicated to all things snow, Schnee Days, held in late January.brThis 2-bedroom condo is in an ideal location to take advantage of all that this area offers throughout the year!

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Sleeps

Exceptional(6)

$1033.03

/ Nightly

Private Vacation Home

Beautiful Country Home Near Popular Hot Spots!

Plymouth, Wisconsin, United States

Stay in our spacious home, that includes two living rooms, as well as a bar area with darts, a pool table and foosball table! Sleeps 10 people. Sit on the backyard deck or around the firepit to enjoy the quiet, nature filled backyard, which often hosts deer and wild turkeys. The entire house is yours, so make yourself at home!brbrLocated 2 minutes from Road America and a quick 5 minute drive to downtown Elkhart Lake or Plymouth! Enjoy the shops, dining and lake!brbrSpace is made available for you in closets, but not all clothing is removed. Linens and towels included. The kitchen is fully stocked with pots, pans, utensils & dishes to make your stay easier! brbrBooking Adjustments: Every effort will be made to accommodate the following requests:brbr~ A request to add days to your reservation and/orbr~ A request to swap or substitute days at the beginning/end of your reservation brbr** A request to reduce days to your reservation will not be accepted.

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Bath

Sleeps

Exceptional(2)

$933.68

/ Nightly

Private Vacation Home

Road America and Golf Retreat

Plymouth, Wisconsin, United States

Escape to tranquility at our charming rental, nestled in serene woods, just down the road from Road America and premier golf courses. Enjoy the beauty of nearby lakes, perfect for relaxing or adventurous outings. Our cozy retreat offers modern amenities and a peaceful atmosphere, making it an ideal getaway for nature lovers, golfers and racing enthusiasts alike. Book now for an unforgettable experience with Victory Investment Properties!

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Bath

Sleeps

Exceptional(56)

$422.0

/ Nightly

Private Vacation Home

Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf

Plymouth, Wisconsin, United States

**2025 and 2026 calendar is open. Please note that our peak season rentals are a week minimum and run Monday-Monday**brbrTo reach Kettle House, you drive across a short bridge to a wooded island. Follow the curved lane past three houses, stopping at the fourth to turn in the driveway and park. Walk across the lane and open the gate. Your vacation begins!brbrTo enter the house, pass through the large patio where a top-of-the-line gas grill sits waiting for its next steak. Going inside, you’re in the great room with a wall of glass doors that open to a balcony overlooking the lake. In addition to a 46” TV, the living space offers a dining area for six. A fireplace is on hand to warm you on cool evenings. brbrEntertain yourselves with WiFi and cable as well as a docking station and games. The kitchen is newly refurbished and well-equipped for a cook. Two queen bedrooms and one bedroom with a twin over full bunk comfortably sleep eight. Kettle House has two full bathrooms, one with a jetted tub and Kohler fixtures; the other is freshly remodeled.brbr Because it straddles an island, the Kettle House property has two shorelines. A screened porch with a bar overlooks the shoreline in front of the house. Relax in the hammock overlooking the lake and enjoy the sunset through the trees.brbrThe second shoreline, Down back, is across the island, where cedar trees make it shady and peaceful. A large grassy field beside this shore will invite your group to play ball or cornhole. Or, launch one of the two provided kayaks. Float toys, water games, and life vests are also available.brbrSometimes you can hear racing over at Road America. Many track events are open to the public, and it’s only five minutes away. A public golf course is within walking distance, and the PGA courses, Whistling Straits and Blackwolf Run, are a 20 minutes drive. If you enjoy biking, hiking, or snowmobiling, you’ll want to visit nearby Kettle Moraine State Park. Elkhart Lake is just up the road, and there you can stock up at the farmer’s market, enjoy the charming shops or eat at one of the town’s good-to-excellent restaurants.

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Bath

Sleeps

Exceptional(1)

$819.74

/ Nightly

Private Vacation Home

3 Min to Road America, outdoor deck, grill, & fire table

Plymouth, Wisconsin, United States

Be one of the first to stay at this newly renovated 5-bedroom, 2.5-bath home. Plenty of space for group getaways, race weekends, or golf trips! Enjoy 2 living spaces with 65-inch Smart TVs, a lower-level bar for entertaining, WiFi, and in-unit laundry.brbrRelax outside on the deck, fire up the grill, or unwind indoors with all the comforts of home.brbrYou will enjoy a comfortable nights sleep with deluxe mattresses, down-alternative comforters, and 4 pillows per bed. Each bedroom window includes blinds and extra blankets are available for your convenience.brbrJust minutes from Road America and Whistling Straits, this is your ideal home base for adventure or relaxation.

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Select Dates for Price

Private Vacation Home

New home on Crystal Lake.

Plymouth, Wisconsin, United States

Lake home completed in 2020 on a 130 acre Crystal Lake which is at the top of the aquifer and therefore crystal clear Near Quit Qui Oc and Lancerlot Golf courses,15 minutes from Whistling Straits as well as many other golf courses. Close to Road America, Ice Age hiking trail, Plank Road biking trail, Shopping and restaurants in Plymouth and Elkhart Lake. Stand up paddle board, 2 single and 2 double kayaks, Sailboat and Pontoon Ride by owner if requested. Hammock, Rope Swing, Chair swing, Slide into water, Fire pit and Gas Grill. Home with deck18 feet from the lake with a good seawall and large pier. Second floor deck overlooking the lake. Garage with workshop.

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Rent a place that suits your needs

Private vacation home

View 37 Private vacation home

Most popular vacation rentals in Plymouth

$414.28

/ Nightly

Private vacation home

House, near Road America, Kohler, Lake Michigan

Plymouth, Wisconsin, United States

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Bath

Sleeps

$661.46

/ Nightly

Private vacation home

Walk to Road America & near Kohler Golf ~ The Woods Estate ~ Modern Luxury

Plymouth, Wisconsin, United States

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Sleeps

$555.09

/ Nightly

Private vacation home

Beautiful, newly built 3rd floor Townhouse in historic Elkhart Lake, WI.

Plymouth, Wisconsin, United States

Bed

Bath

Sleeps

$522.87

/ Nightly

Private vacation home

Hot Tub, Kayaks, SUP's & Firepit

Plymouth, Wisconsin, United States

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Bath

Sleeps

$504.00

/ Nightly

Private vacation home

Private home on twenty wooded acres.

Plymouth, Wisconsin, United States

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Bath

Sleeps

$487.06

/ Nightly

Private vacation home

One Minute to Road America - Close to PGA Golfing

Plymouth, Wisconsin, United States

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Sleeps

$439.31

/ Nightly

Country House

Sleeps 13 - Hot Tub - Game Room - minutes from Road America

Plymouth, Wisconsin, United States

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Sleeps

$422.00

/ Nightly

Private vacation home

Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf

Plymouth, Wisconsin, United States

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Sleeps

$232.08

/ Nightly

Villa

Country Cheese Factory - King Bed!

Plymouth, Wisconsin, United States

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Bath

Sleeps

$265.33

/ Nightly

Private vacation home

Wyatt's Country Home - King Bed!

Plymouth, Wisconsin, United States

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Bath

Sleeps

Vacation Home Rentals By Owner In Plymouth, WI

$522.87

$663.91

$702.32

$809.63

$1017.33

$487.06

$755.54

$983.67

$1002.25

$265.33

$555.09

$1033.03

$933.68

$422.0

$819.74

Rent a place that suits your needs

Most popular vacation rentals in Plymouth

$414.28

$661.46

$555.09

$522.87

$504.00

$487.06

$439.31

$422.00

$232.08

$265.33

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