Vacation Home Rentals By Owner In Plymouth, WI

$868.99

Elkhart Lake Oasis - 25 Acres, Hot Tub & Orchard - 15 Min to Road America

Plymouth, Wisconsin, United States

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. Just 15 min from Road America and Elkhart Lake. Built for race teams, race fans, and families looking for a luxurious summer getaway.brbrWelcome to Your Elkhart Lake OasisbrStep into your own private retreat on 25 acres of maple woods, walking trails, and a working apple orchard. Whether you're here for a Road America race weekend, a round of world-class golf at Kohler, a day on Elkhart Lake, or simply to slow down and reconnect, this villa gives you the space, comfort, and setting to truly recover between adventures.brbrDesigned for race teams, race fans, and families who want a real getaway:br• 4 bedrooms, 2.5 bathrooms — sleeps 8 comfortablybr• Chef's kitchen, fully stocked to cook for the whole crewbr• Two indoor fireplaces + outdoor fire pit for after-race nightsbr• 3-season sunroom with fireplace — feels like sitting in the woodsbr• In-home gym: treadmill, weights, heavy bagbr• Hot tub under the starsbr• Vaulted great room, office, kids' playroom, EV charger, 1Gbps WiFibrbrStep Outside Tobr• Private apple orchard and maple woodsbr• Walking trails and wildlife right out the back doorbr• Expansive patio for grilling, gathering, and unwindingbr• Fire pit for stargazing, stories, and s'moresbrbr15 Minutes to It Allbr• Road America (race weekends, track days, driving experiences)br• Elkhart Lake dining, shops, and beachesbr• Kohler Spa, Whistling Straits, and Blackwolf Run (~25 min)br• Reasonable drive to Oshkosh EAA and Green Bay footballbr• 25 min to Lake MichiganbrbrComfortable Bedrooms for Everyonebr4 bedrooms and 2.5 bathrooms, sleeping up to 8:br• Primary suite: king bed, en-suite bath, views of naturebr• Bedroom 2: queen bedbr• Bedroom 3: queen bedbr• Bedroom 4: twin bedsbr• Family room: two twin beds (great for kids)brbrGather, Cook & RecoverbrThe open-concept layout makes it easy for families and race teams to spend time together, then spread out to recover.br• Cook in the fully equipped chef's kitchen with high-end appliancesbr• Share meals at the spacious dining tablebr• Relax in the vaulted great room with big windows on the woodsbr• Start or end your day in the sunroom by the fireplacebr• Recover in the in-home gym between race daysbrbrThe Practical Stuffbr• 1Gbps WiFi for work or streamingbr• Washer & dryer on-sitebr• Ample on-site parking with space for trailers and team haulers — a top reason Road America race teams choose this propertybr• EV charger (Tesla-compatible)br• Smart TVs for movie nightsbr• Central heating & cooling for year-round comfortbrbrWhy Guests Come BackbrMany homes near Road America offer a place to stay. Few offer:br• The total privacy of 25 quiet acres in the maple woodsbr• A luxurious, family-friendly home built for the way race teams and families actually travelbr• A location just minutes from the area's top attractionsbrbrIt's a rare mix of privacy, comfort, and convenience — room to spread out, room to recover, room to celebrate. Whether you're here for racing, golf, the lake, or a family getaway, your private Elkhart Lake oasis is ready. We look forward to hosting you!

Bed

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Sleeps

$822.03

/ Nightly

Private Vacation Home

Beautiful home - Great for Road America, golf outings, NFL Draft, or just R&R!

Plymouth, Wisconsin, United States

Beautiful home in a quiet neighborhood. Less than a minute from Road America, 10 minutes to Elkhart Lake. Enjoy the tourist areas around Plymouth, Elkhart Lake, Sheboygan, etc. Sit on the front porch or deck area and enjoy the quiet atmosphere or take a ride to Elkhart or Plymouth to enjoy the events, little shops, coffee shops, bars and restaurants. A nice area in the summer time!

Bed

Bath

Sleeps

$289.82

/ Nightly

Private Vacation Home

Chic Plymouth Townhome < 1 Mi to Road America

Plymouth, Wisconsin, United States

Prepare for an unforgettable retreat at this 2-bedroom, 2-bathroom Plymouth vacation rental next to Road America! Nestled between Sheboygan and the natural beauty of the Kettle Moraine, this condo offers easy access to city fun and outdoor adventure. Enjoy days on the water of Elkhart Lake or head east to cruise along Lake Michigan. When you’re not on the water, hit a hike or catch an event at the track. Return to these updated digs for a drink on the balcony and a movie on the Smart TV.brbr-- THE PROPERTY --brbr3 Smart TVs | Balcony w/ High-Top Table | Patio w/ SeatingbrbrBedroom 1: California King Bed | Bedroom 2: Twin/Full Bunk Bed | Living Room: Full Sleeper SofabrbrTOWNHOME FEATURES: Fireplace, cable (bedroom 2 only), books, ceiling fansbrKITCHEN: Dishwasher, electric stove/oven, refrigerator, microwave, breakfast bar w/ seating, cooking basics, dishware & flatware, blender, coffee maker, coffee grinder, toaster, trash bags & paper towelsbrGENERAL: Free WiFi, central A/C & heating, complimentary toiletries, linens & towels, laundry detergent, hair dryer, hangers, iron & board, keyless entrybrFAQ: Not childproofed, upper-level unit, long-term tenant in lower unit, 1 external security camera (facing out), quiet hours (10:00 PM-8:00 AM), no grillbrACCESSIBILITY: Single-story condo, 2nd-floor unit, interior steps to enter brPARKING: Driveway (3 vehicles), no garage accessbrbr-- THE LOCATION --brbrOUTDOOR RECREATION: Little Elkhart Lake (0.7 miles), Elkhart Lake (3.0 miles), Gerber Lake Preservation Area (3.5 miles), Ice Age Trail Greenbush Trailhead (4.1 miles), Sheboygan Marsh State Wildlife Area (7.7 miles), Greenbush Trails (9.3 miles), Parnell Tower Loop Trail (13.1 miles), Lake Michigan (17.9 miles), Kohler Park Dunes State Natural Area (22.6 miles), Kettle Moraine State Forest (27.6 miles)brWINTER FUN: Nutt Hill Ski Area (4.7 miles), Greenbush Recreation Area (8.9 miles), downhill skiing, cross-country skiing, snowmobilingbrTHINGS TO SEE & DO: Road America (0.5 miles), Quit Qui Oc Golf Club & Restaurant (2.4 miles), Wade House Historic Site (7.9 miles), Quarry Beach Adventure Park and Water Sports (15.3 miles), Shalom Wildlife Zoo (26.7 miles)brDOWNTOWN SHEBOYGAN (17.3 miles): John Michael Kohler Arts Center, Bookworm Gardens, Deland Park, Above & Beyond Children's Museum, Sheboygan County Historical MuseumbrAIRPORTS: Appleton International Airport (54.7 miles), Green Bay Austin Straubel International Airport (58.0 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This single-story condo on the 2nd floor requires an interior staircase to enter br- NOTE: This property is the upper-level unit. There are long-term tenants in the lower-level unit and they may be present during your staybr- NOTE: The property is not childproofed and may not be suitable for young children. Young children must be careful and use caution on bunk bedsbr- NOTE: The property does not have a grill br- NOTE: Your safety matters. This property features 1 exterior security camera located at the front door facing the front exterior entry. It does not look into any interior spaces. The camera records video and sound when activated by motionbr- NOTE: Please be respectful of the year-round community residents and respect quiet hours between 10:00 PM-8:00 AM

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Bath

Sleeps

$317.54

/ Nightly

Private Vacation Home

Walk to Road America-Private Getaway with Views + Loft + Fire Pit

Plymouth, Wisconsin, United States

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.brbrThe cottage features an open-concept layout designed for comfort, connection, and easy entertaining.brbrMain Level-brbrSpacious living room with vaulted ceilingsbrComfortable seating and 55” Smart TV (log into your Netflix, Prime, Hulu & more)brLarge windows and patio door leading to the deckbrOpen kitchen with:brIsland seating for 5brDining table, seating for 4 (perfect for meals or card games)brFully stocked kitchen + full-size dishwasherbrbrPrivate primary bedroom with plush king bed, two large closets and a at home workspace.brNewly updated bathroom with double sinks, tub/shower combo, and ample counter spacebrbrLoft-brbrUnique spiral staircase leads to a fun loft spacebr4 built-in twin bedsbrOverlooks the living area and showcases beautiful viewsbrbrOutdoor Living-brbrWrap-around deck with scenic hillside and pond viewsbrFirepit for s’mores and pudgy pies (summer months)brCharcoal grill (please no grilling on the wood deck)brbrThis is our favorite spot! Perfect for quiet mornings or winding down after a busy day.brbrParking & Access-brbrPlenty of parking on sitebrLarge trailers and RVs welcomebrAdditional parking available in the north drivewaybrGuests have full access to the main level and loftbrBasement is lockedbrKeyless entry with personalized door codebrbrWhat’s All Provided-brbrWe want you to pack light and feel at home:brbrAll bedding, pillows, and extra blanketsbrBath towels, washcloths, shampoo, conditioner, soap & hair dryerbrKitchen essentials including:brDish soap & dishwasher detergentbrSalt, pepper, cooking oilbrCoffeebrbrGuests will have full access to the main level and the loft. We will provide you with a door code to let yourself in.brbrDuring the summer months, especially weekends, there will be noise from Road America Racetrack across the street. We are very close to the action and all the excitement happening there.brbrCheck in time 4:00pm brCheck out time 10:00am brPlease let me know if these times do not work, I am flexible and willing to adjust times if able. Just let me know. brbrNo Parties.brbrNo smoking or vaping inside the home.brbrThere is a Ring doorbell camera at the front entrance and two cameras overlooking both driveways for security purposes. No cameras are located inside or in private outdoor spaces.brbrbrSome nearby area attractions...brbrDowntown Elkhart Lake village restaurants, shops and Saturday Farmers MarketbrbrLittle Elkhart Lake, Elkhart Lake, and Crystal Lake are all nearby for fishing off a pier. brbrRoad America .2 miles (2 min WALK)brQuit Qui OC Golf Course 2.2 miles (4 min drive)brElkhart Lake’s Fireman’s Public Beach 2.3 miles (4 min drive)brCrystal Lake Boat Launch 2.3 miles (5 min drive)brElkhart Lake Boat Launch 4.0 miles (7 min drive) brIce Age Trail 4.5 miles (6 min drive)brSheboygan County Marsh Tower 5.1 miles (9 min drive)brKettle Moraine Hiking/Biking Trails State Forest 9 miles (10 min drive)brWade House 9.5miles (11 min drive)brParnell Tower 13.5 miles (17 min drive)brKohler Water Spa 15 miles (15 min drive)brWhistling Straights Golf Course 15.3 miles (20 min drive)brLake Michigan 18.4 miles (23 min drive)brBlue Harbor Resort 19 miles (24 min drive)brEAA 46 miles (51 min drive)brbrbrElkhart Lake- 4 min drivebrPlymouth- 7 min drivebrKohler- 16 min drivebrSheboygan is- 20 min drivebrFond du Lac- 33 min drive

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Sleeps

$338.11

/ Nightly

Private Vacation Home

>>The Daydream Lodge<< @Racers Ridge

Plymouth, Wisconsin, United States

Relaxing.Racing.Golfing.brExploring. brThis spacious 3 bedroom home is perfect for a tranquil getaway or as a base camp for adventure. 5 minutes from Road America, 5 miles from Elkhart Lake, & a short drive to all of the area golf courses. This home overlooks Crystal Lake for beautiful sunrises. Public access is 1/4 mile away, use our kayaks to paddle the tranquil waters. This rustic home with modern furnishings has it all: 2 1/2 bath, fireplace, game room, large deck, and huge yard w/ firepit.

Bed

Bath

Sleeps

$544.4

/ Nightly

Private Vacation Home

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth, Wisconsin, United States

Welcome to The Hemisphere House, a unique dome retreat in a charming Wisconsin neighborhood. This architectural gem offers three bedrooms, a bunk room, and three bathrooms. Enjoy the game room with arcade games and a pool table, a cozy living area with a fireplace, and a fully equipped kitchen. Relax on the private deck or gather around the outdoor fire pit. Nearby attractions include hiking, fishing, kayaking, Road America Race Course, and local golf courses. Book now for an unforgettable stay!

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Bath

Sleeps

$907.28

/ Nightly

Private Vacation Home

Stunning custom built country home with the ultimate game room!

Plymouth, Wisconsin, United States

Welcome to Oak Haven, a private 4,300 sq ft retreat surrounded by oak trees and peaceful Wisconsin beauty. brbr• 12-seat movie theater with plush recliners & surround sound br• Game room with pool, ping pong, shuffleboard & poker br• Infrared sauna + two outdoor fire spots for perfect nights br• Gourmet kitchen & dining for twelve ️br• Minutes to Kohler golf, Kettle Moraine & Road America ️brbr✨ Oak Haven—where relaxation, laughter, and connection come naturally.brThe spacebr Oak Haven | Theater • Game Room • Sauna • Firepits • Near Kohler & Road AmericabrbrWelcome to Oak Haven, part of the Wisconsin Getaways Collection — where every stay is designed for connection, comfort, and unforgettable moments. brbrThis 4,300 sq ft wooded retreat pairs the peace of nature with the luxury of a thoughtfully curated home. Guests call it “spotless, spacious, and even better than the photos” and rave that “the theater and game room made us never want to leave.”brbrWhether you’re reuniting with friends, celebrating family milestones, or escaping for a peaceful reset, Oak Haven captures everything that makes Wisconsin Getaways beloved across the state: breathtaking settings, exceptional design, and a host team that truly cares. ✨brbrbrbr The SpacebrbrbrMain Floorbrbr ️ Bedroom 1 – King Bed + Ensuite (Full Bath #1) with walk-in shower & soaking tubbrbr Bedroom 2 – Queen Bed + Fireplace, cozy and private near the entrybrbr Gourmet Kitchen with marble counters, stainless appliances & deck accessbrbr ️ Massive Dining Table for twelve — perfect for shared meals & laughterbrbr Living Room with stone fireplace & views of the surrounding oaksbrbr Half Bath off the kitchenbrbr Walkout Deck with gazebo, two firepits (gas & wood), and plenty of seatingbrbrbrbrUpstairsbrbr ️ Bedroom 3 – Queen Bedbrbr ️ Bedroom 4 – Queen Bed + Crib (ideal for families)brbr ️ Bedroom 5 – Two Queen Bedsbrbr Full Bath #2 with tub/shower combobrbrbrbrLower Level – The Fun ZonebrbrWhere guests say “we hardly left the house.”brbr 12-Seat Theater with plush recliners, surround sound & popcorn machinebrbr Pool Table, Ping Pong, Shuffleboard, Air Hockey & Poker Tablebrbr Infrared Sauna for relaxation after a day of adventurebrbr Full Bath #3 with walk-in showerbrbrbrbr✨ What Guests Lovebrbr“Spotless, spacious, and exactly as described.” – Jim, ILbr“The game room and theater were unbelievable—we never wanted to leave.” – Sarah, WIbr“Perfect for big families—kids played for hours while we relaxed.” – Sabrina, WIbr“Peaceful, private, and close to everything we needed.” – Steve, TXbr“One of our favorite Wisconsin Getaways stays—Tyler was amazing!” – Korie, MIbrbrbrbr Highlightsbrbr12-seat movie theater with surround sound & reclinersbrbrFully loaded game room with billiards, ping pong & pokerbrbrInfrared sauna + two firepits for cozy nightsbrbrGourmet kitchen & large dining areabrbrPeaceful wooded setting | Sleeps up to 14 guestsbrbrLuxury bedding, smart keyless entry & 3-car heated garagebrbrProfessionally cleaned & maintained by Wisconsin Getawaysbrbrbrbr ️ Close To EverythingbrbrLocated in the heart of Sheboygan County — secluded, yet near it all:brbr ️ Road America – 15 minutesbrbr⛳ Whistling Straits & Blackwolf Run – under 25 minutesbrbr Kettle Moraine State Forest – 125+ miles of trailsbrbr Destination Kohler – world-class dining & spabrbrGuests love that “you feel far from it all, yet close to everything that matters.”brbrbrbr ‍ Enhance Your StaybrbrAs with every Wisconsin Getaways property, we offer optional private chef experiences, grocery pre-stocking, and celebration packages upon request.brOur dedicated team is known for “fast, friendly communication and going above and beyond.”brbrbrbr ️ Additional DetailsbrbrHigh-speed WiFi & smart TVsbrbrWasher & dryerbrbrCentral heat & air conditioningbrbrHeated 3-car garage (winter parking required for plow access)brbrbrbr The Wisconsin Getaways ExperiencebrbrFrom Malibu House on Lake Michigan to The Grand on Longtail, our homes are designed for those who value time together. Oak Haven continues that tradition — a place where families gather, friends laugh late into the night, and every guest feels cared for.brbrAs one reviewer perfectly put it:brbr“It’s peaceful, private, and full of memories waiting to happen.”brbrbrbr✨ Oak Haven — proudly hosted by Wisconsin Getaways, where luxury meets warmth and every stay feels like home.brGuest accessbrThere will be a keyless entry available at the door. The key code will be given during reservation. Contact me for details.brOther things to notebrWe have indoor parking available for three cars. We ask that you please park all vehicles inside in the winter to allow for snow plow services.brbrPlease let us know how we can make your stay extra special.brbr Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbrbr Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limitsbr Maintain respectful noise levelsbr No outdoor speakers or amplified musicbr No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 6 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.brbrIn alignment with our ongoing commitment to guest safety and comfort, this property has been inspected and approved as a lodging establishment by the Wisconsin Department of Agriculture, Trade and Consumer Protection. brbrFollow @WisconsinGetaways for updates, specials, and new property launches.br Important — Guest Verification Required After BookingbrbrTo ensure a smooth and secure stay, all reservations complete a quick post-booking verification directly with Wisconsin Getaways. This secure step is completed outside of the platform and includes:brbr Providing a valid driver’s license or government-issued ID for the primary guestbr✍️ Signing our standard rental agreement directly with the HostbrbrThese items simply reaffirm the house rules shown here and do not override Airbnb or Vrbo’s Terms. Once completed, you’ll receive your arrival instructions—property address, parking details, and door codes—typically two weeks before check-in.brbr Quiet Community SettingbrbrMany of our homes are located in peaceful lakefront and residential neighborhoods. Guests love the tranquility, and we ask everyone to be mindful of neighbors and keep outdoor noise low, especially in the evenings. This helps maintain the relaxing atmosphere our properties are known for.brbr House Standards (Must Be Followed)brbrTo keep our homes and communities in excellent condition, the following expectations are firmly enforced:brbr Stay within posted occupancy limits (including visitors)br Maintain respectful noise levels (neighbors should not hear yelling or cursing at any time)br No outdoor speakers or amplified music (leave your speakers at home)br No unauthorized gatherings or eventsbr No indoor smoking ($600 violation)br Guests may bring a total of up to 6 vehicles. When a garage is available, it must be used to help limit the number of cars in the driveway. Absolutely no street parking is allowed at any time.brbrThese guidelines ensure every guest enjoys the high-quality, peaceful experience Wisconsin Getaways is known for.

Bed

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Sleeps

$498

/ Nightly

Private Vacation Home

Private home on twenty wooded acres.

Plymouth, Wisconsin, United States

Located in the Northern Kettle Moraine Forest, this property is an hour north of Milwaukee and one hour and twenty minutes south of Green Bay. The house sits in the middle of twenty wooded acres with a quarter mile long paved driveway. A haven for ephemeral flowers in spring, beautiful fall colors, and wildlife year round, this is a nature lover's paradise. Hiking trails on the property let you see it all. brbrThis recently purchased 30 year old country cottage has been fully renovated and is available specifically for vacation rental use. With two bedrooms (full bath) on the main floor and one on the second floor loft (bath with shower), it comfortably sleeps six (all queen size beds). The kitchen has new cabinets with all new appliances (stove, refrigerator, dishwasher) and a patio door that opens onto a small deck area. An island with four chairs separates the kitchen from the dining room which has a table and six chairs. Windows all around let you enjoy the beautiful scenery. The living room (leather furniture, TV, DVD, bring your own WIFI) has an adjoining three season porch. The second floor loft runs the full length of the house. It features a seating area in the sunroom with a panoramic view of kames in the surrounding area. Patio doors in the bedroom area open to a large deck facing the woods. The rec room in the walk-out basement has a pool table, dart machine, foose ball table, TV, and bar. New washer and dryer are in an adjoining room. Outside is a cement patio with new gas grill.

2

Bath

6

Sleeps

Exceptional(20)

$815.86

/ Nightly

Private Vacation Home

Summit Woods Hideaway! Walking Distance To Road America. Elkhart Lake, WI 53020

Plymouth, Wisconsin, United States

Experience everything Road America and Elkhart Lake have to offer. This 2,500+ sqft home finished construction in November of 2016. It has 4 bedrooms and 3 full baths, quartz counter tops and a great open concept layout that makes it easy to relax. The house has a brand new kitchen and island with quartz counter tops and all new stainless steel appliances. A master bedroom with a king bed along with a private master bathroom, tile shower with glass doors and his and hers sinks allow plenty of room for guests. The other 2 bedrooms on the main level share a full bath. Each of the spare bedrooms on the main level has 2 more beds. There is an additional queen bed/bedroom in the basement along with a full bath in the basement. The lower level living room features a 75 TV, bar with a beer fridge and access to the patio. This home comes with all the standard amenities including a washer and dryer and room to park several vehicles in the driveway.brbrThe exterior of the property boasts a beautiful deck looking out towards the 3/4 acre property and Road America's main gate. A patio with table and chairs and stainless steel BBQ are also available for guests to use.brbrWith 2 TV's with YouTube TV, WiFi, central air and heating, fireplace, outdoor deck and patio this is the perfect home for your retreat.brbrNearby Elkhart Lake hosts many restaurants, bars, live music, sandy public beach and shopping.brbrKey Words: Plymouth, WI 53073, Elkhart Lake, WI 53020, Kohler, WI, rent, rental, vacation, road america, golf

Bed

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Sleeps

$774.39

/ Nightly

Private Vacation Home

Beautiful private home hidden in the woods. Can sleep 11 guests

Plymouth, Wisconsin, United States

NEW FOR 2025 BRAND NEW 7 person hot tub added to a beautiful rebuilt front deck along with deck lighting to-make this a relaxing getaway. PLEASE READ…THIS IS NOT A PARTY LOCATION & NO LARGE PARTIES ARE ALLOWED Located on the edge of Plymouth, WI and a 1/2 mile to Hwy 23 for fast access to any major event in the area. Ranch home with no neighbors, tucked in the woods & close to town. Beautiful open floor concept with gas fireplace, pool table, fooz ball table, large dining table, comfortable couches. Huge master bedroom with king size bed & walk in closet. Minutes from Road America & 20 minutes to Whistling Straits golf course home for the 2021 Ryder cup. Less than 5 minutes into town for bars, restaurants, gas stations and stores. 2 bedrooms, 1 king size bed & 1 queen size bed. Couch upstairs & in the basement, full size mattress with linen, 2 Queen size blow up mattress’s with foam padding are available with linens & pillows upon request to sleep up to 11 quests. Treadmill, elliptical machine and free weights are available in the basement. Attached garage is available to park inside. Ford F-150 crew cab with short box will fit but anything bigger will not. Check in & check out times are very flexible... please message me with any specific requests. Thank you. Please clean up after yourself.. we do not charge a cleaning fee but ask that you leave the property the same way you found it with the exception of dirty towels & bed linen!! We ask that you do not host any parties & that you treat this like your own home.

Bed

Bath

Sleeps

$527.5

/ Nightly

Private Vacation Home

Retreat to Crystal Lake

Plymouth, Wisconsin, United States

Beautiful Home on Crystal Lake. 120 feet of lake frontage. Large front yard and patio allows you to enjoy the beautiful sunset.brKayaks, fire pit and much more.brFantastic game room with Pool Table, Dart Board, TV and bar.br4 bed rooms, 2.5 baths. Sleeps 10brPlenty of Parking

4

Bed

2

Bath

10

Sleeps

$512.07

/ Nightly

Private Vacation Home

Amazing 5-bedroom Victorian house Downtown Plymouth 6 minutes from Road America

Plymouth, Wisconsin, United States

The Vibrant Victorian ~ Downtown Plymouth was restored in fall of 2025-2026 and we focused on creating a unique downtown stay. The location offers a quick stroll to Plymouth’s charming downtown (situated just 1 block from Mill St.) Explore shops, pubs, and restaurants in the heart of Plymouth. Whether you plan to spend your days with down town adventures, kettle hikes, a visit to Elkhart Lake, or golfing at one of many renown golf courses as close as Kohler, WI (Black Wolf Run is just 16 miles) this is the space for you.brbrThe space: brbrCarefully curated, relaxing spaces have been designed with visitors in mind from the beginning. brIt’s perfectly imperfect, filled with the character of dings and scratches, and craftsmanship of a 125 year old house. The home features modernized but classic kitchen and 2 luxurious baths including a heated floor, a dual head rain shower and a soaking tub. End your days with crisp and clean soft beds set for deep restful sleeps. Sleeps 12 with 4 traditional bedrooms and one pass through bedroom that can flex from twin bed to a king depending on your desired stay. One first floor bedroom provides for accessibility and four upstairs. Appreciate natural woodwork, restored original windows/doors, wood floors, and whimsical wall papers. A large main living room, a cozy parlor (with fireplace and record player), formal dining room finish off the first floor. Enjoy drink stations for your convenience with espresso/coffee/tea upstairs and down, mix a cocktail at the bar cart if you desire. Outside (depending on season) you’ll find 4 porches with chairs to rock in, white railings, an effortless gas fire at dusk on porch or build a natural fire on the patio. Under 2 blocks to downtown East Mill St. for a meal out and about or tour the historic downtown. Come to visit, the Vibrant Victorian, downtown Plymouth awaits. Thanks for visiting!

Bed

Bath

Sleeps

$414.28

/ Nightly

Private Vacation Home

House, near Road America, Kohler, Lake Michigan

Plymouth, Wisconsin, United States

Welcome! Warm spacious 3 bed/2 bath ranch home for rent. Our home is your home. Living room & Family Room. Master Bedroom with large tile shower in Master Bedroom. Quiet spacious backyard with patio and BBQ and fire pit. 10 minutes to Road America. Short drive to Sheboygan’s Lake Michigan and Kohler Golf Courses. We don’t charge extra cleaning fees!- We now have WiFi!!!! During December, January, February and March we rent by the month if you have rented previously, text us 920-838-1747!

Bed

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Sleeps

$661.46

/ Nightly

Private Vacation Home

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

Plymouth, Wisconsin, United States

Experience the beauty & comfort if this luxury contemporary home nestled in the woods on 5 acres walking distance to Road America & near Golf. It’s a very peaceful setting and yet conveniently located close to many restaurants and things to do. brEnjoy views of nature from the windows. Check at dawn & dust for the deer, hear the owls hooting and stargaze at the perfect night sky. brbrSpacious ~ 3 living rooms & 4 bedrooms with 6 beds (1 king, 4 queens, 1 full) brbrKid friendly kid play area brFree WiFi (Disney, netflix, Amazon prime)brbrAcross the street from Road America. 14 mile to Whistling Straits, 10 min to Kohler, 4 min to Elkhart Lake & Plymouth. brbrMore details: The 20 foot ceilings in the living room make the space feel very open. The smart TV makes it the perfect spot to kick back and relax! (Fireplace usage is not permitted) brbrThe first floor master bedroom (king) includes french doors to a private brdeck, it’s a great place to enjoy a morning cup of coffee. brThe en-suite bathroom is a KOHLER smart bathroom. It includes a Kohler toilet with bidet option and a huge Kohler smart shower with 8 shower sprays and a rain shower spray. brbrThe second bedroom includes 2 queen beds, third bedroom queen bed, fourth bedroom a double bed and there’s one more queen in the loft living room space. brbrOur first floor laundry room with washer/ dryer / iron and ironing board is also available for your convenience. brbrThe home also includes a large secondbr living room / sunroom with gorgeous views of the garden and woods. Along with top of the line LG Oleg tv and switch gaming system. brbrAlso there is one more living in the upstairs loft area. It’s the perfect place to watch a movie, or fun play spot for kids! The couch up here is really big, works great if you need an extra place to sleep. brbrOutdoor fire pit, grill, cornhole game and seating area are also available for use. brbrSit back and relax amongst the trees in the hammock. Take a dip in the outdoor hot tub. brbrWalk across our street to Road America. brbrWe’re 4 miles to the beach in Elkhart Lake. Tons of watersport rentals are available at Elkhart Lake. 10 miles from Kohler, and 14 miles from Whistling Straits Golf Course. brbrThe Kettle Moraine nature trails are only 6 miles away where you can hike, bike, cross county ski, ride horses, fish and ride snowmobiles.brbrWe are conveniently located 1 hour north of Milwaukee and 1 hour south of Green Bay.

4

Bed

2

Bath

12

Sleeps

$727.95

/ Nightly

Private Vacation Home

Walk to Road America Races. Enjoy the lake frontage and fishing and kayaking.

Plymouth, Wisconsin, United States

Located on Little Elkhart Lake walking distance to Road America. Private 450' of waterfront on a peninsula with undeveloped natural view across lake. Four bedroom, three and a half bathrooms with kitchen, family room, screen porch, pool table room, large deck and fire pit.brbrPier and anchored swimming raft plus fishing rowboat, kayaks, paddle boards, pedal boat and other water toys included in rental. Walk right into the water and enjoy this small quiet lake popular for fishing, kayaking, and swimming. Life vests available.brbrParking available for four cars. One minute to Road America, 5 minutes to downtown Elkhart Lake. Plenty of room to relax on one of the most peaceful, private lakefront properties around. Bunk bed room with three bunk bed sets is fun for the kids. A pack and play, baby gate and child monitor is available. This area is a great destination for golf, Road America, lovely cafes and shops, a huge commercial great swimming beach 5 minutes away on Elkhart Lake.brbrWinter activities are plentiful. Ice fishing and skating or just pulling a sled over the lake is fun. Rent cross country skis or snowshoes from Osthoff in Elkhart Lake three miles away. Skating in Sheboygan. So much winter fun!

Bed

Bath

Sleeps

$798.24

/ Nightly

Private Vacation Home

Lake House-Kayaks/Paddle Boards/Private Pier

Plymouth, Wisconsin, United States

Luxury Lakefront Living w/ Private Pier, Kayaks, & More on Crystal LakebrbrWelcome to the Crystal Lake Beauty hosted by Sheboygan Vacation Rentals. Be one of the first to experience this professionally redesigned, lakefront retreat—a stunning blend of comfort, style, and family-friendly fun nestled on the shores of Crystal Lake.brbrThis spacious 4-bedroom, 2.5-bath home has been thoughtfully renovated from top to bottom with all-new, high-end furnishings, designer decor, premium beds, linens, and modern finishes throughout. Every detail has been curated to offer an upscale yet welcoming experience that’s perfect for families, couples, and groups looking for a luxurious home base in central Wisconsin.brbr Lakefront LuxurybrStep outside and take in the serene beauty of Crystal Lake from your private pier. Spend your mornings with coffee on the dock, your afternoons paddling in the included kayaks and paddleboards, and your evenings watching the sunset ripple across the water. This is what lake life dreams are made of.brbrProvided Lake Amenitiesbr- Two Kayaksbr- Two Stand-Up Paddle Boardsbr- Lily Pad Raftbr- Paddle Boatbr- Life Jacketsbr- Dock w/ two sets of stairs into the crystal clear lake.br- Various other water toys and floatiesbrbr Interior Highlights:brAll-new furniture & decor curated by professional designersbrFully equipped kitchen with modern appliances for easy, at-home mealsbrSpacious open-concept living area with cozy seating and smart TVbr4 bedrooms with brand-new mattresses and hotel-quality linensbr2.5 sparkling bathrooms, freshly remodeled for comfort and stylebrFast WiFi, central A/C, laundry room, and plenty of parkingbr Ideal Central Location:brJust 5 minutes to Road America – a must for motorsport fansbrOnly 20 minutes to the world-renowned Kohler golf courses and spabrUnder 1 hour to both Green Bay’s iconic Lambeau Field and the vibrant energy of MilwaukeebrWhether you’re here to unwind lakeside, explore the region’s top attractions, or host an unforgettable family getaway, this one-of-a-kind Crystal Lake home delivers a five-star experience in every season.brbr Book your stay today and be among the first to enjoy this elevated lake retreat—where every detail has been designed with your comfort in mind.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 are seasonal and may not be available in the Fall/Winter/Spring past October 1st or prior to May 21st. Please inquire.

Bed

Bath

Sleeps

$288.01

/ Nightly

Private Vacation Home

Riverview Getaway

Plymouth, Wisconsin, United States

Lower level of a beautiful, spacious riverfront house built in classic Frank Lloyd Wright style. Lovely views from both home and yard with easy access to river. Located in quaint Plymouth, Wisconsin “Cheese capital of the world.brbrLower level sleeps 6 total. 1Bedroom (2 full sized beds sleeps 4), 1 Full Bath, kitchenette, living room (2-Sofa Sleepers, sleeps 2), dining room, separate private keyed entry. Newly remodeled with fireplace, barbecue area, fire pits and two TVs. Lots of wildlife sharing the property. Kayaks, canoe, golf clubs and bocce ball are available for use. brbrJust minutes away from Road America, Elkhart Lake, and Kohler. Two blocks from Sheboygan County fairgrounds, and race track. 20 minutes from Whistling Straits, many golf courses nearby. Aquatic center just a short walk across river footbridge offering miniature golf, skatepark, hiking trails and lots of spacious parks and playgrounds.

1

Bed

1

Bath

6

Sleeps

$840.87

/ Nightly

Private Vacation Home

Woodsy Hideaway: Game Room, Theater Room, Fire Pit

Plymouth, Wisconsin, United States

Vaulted Ceilings | Vintage Fireplace | Ping-Pong, Foosball & DartboardbrbrWelcome to 'Highland Hideaway' — eclectic, inviting, and just 8 miles from Elkhart Lake! Spend your days at Road America, golfing the legendary Whistling Straits, or hiking the Ice Age Trail, then come home to unwind by the vintage fireplace, put on a record under soaring vaulted ceilings, or spend quality time in the game room. This Sheboygan County vacation rental is the perfect home base for your Kettle Moraine getaway!brbr-- THE PROPERTY --brbrOPEN-CONCEPT LIVINGbr- Spacious living/dining areabr- Natural lightbr- Smart TVsbr- Vintage fireplacebr- Eclectic sitting areabr- Record player w/ recordsbr- Central A/C & heatbr- Theater roombr- Atari gaming consolebrbrOUTDOOR LIVINGbr- Deck w/ diningbr- Forested viewsbr- Garage game roombr- Foosball, ping-pong, dartboard, bar w/ Smart TVbrbrKITCHENbr- Refrigerator, stove/oven, microwavebr- Cooking basics, dishware & flatware, dishwasherbr- Keurig coffee maker (coffee provided)brbrACCESSIBILITYbr- Multi-level home, threshold step to enter (orange garage service door)br- Bedroom & bathroom on main floorbrbrPARKINGbr- Driveway (9 vehicles)brbr-- THE LOCATION --brbr- Walkable to parks, cafes, dining, grocery stores, shops & convenience storesbr- Less than a mile to Evergreen Golf Course (par 3)br- 1 mile to downtown Plymouthbr- 8 miles to Elkhart Lakebr- 6 miles to Road America eventsbr- 14 miles to Stefanie H. Weill Center for the Performing Artsbr- 15 miles to Lake Michiganbr- 8-20 miles to premier golf courses: Quit Qui Oc Golf Club, The Bull at Pinehurst, Blackwolf Run, Whistling Straitsbr- 50 miles to Oshkosh: EAA, The Performing Arts Center: The Grand Oshkoshbr- 51 miles to Milwaukee & 74 miles to Green Baybrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Please remove shoes indoorsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This multi-level property requires a threshold step to enter via the orange garage service door; there is a bedroom and bathroom on the main floorbrbrSECURITY CAMERA INFORMATIONbr- 1 exterior devicebr- Location: orange service door to garagebr- Coverage: entrance area

Bed

Bath

Sleeps

$231.59

/ Nightly

Private Vacation Home

Updated Plymouth Home ~ 5 Mi to Road America!

Plymouth, Wisconsin, United States

Get ready for an unforgettable getaway at this charming 3-bedroom, 1.5-bath vacation rental in Plymouth! Located just a short drive away from top attractions like Road America and Elkhart Lake, this home is the perfect base for your adventures. After a day of exploring, relax on the patio and enjoy outdoor dining with stunning views. Inside, you'll find a cozy living area, a fully equipped kitchen, and comfortable bedrooms. Experience the best of Wisconsin when you stay in this delightful home.brbr-- THE PROPERTY --brbr1 Acre | Free WiFi | 1,233 Sq FtbrbrBedroom 1: Queen Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed brbrHOME FEATURES: Smart TVs, dining table, ceiling fans, outdoor dining tablebr KITCHEN: Refrigerator, stove/oven, Keurig coffee maker, microwave, dishwasher, dishware & flatwarebrGENERAL: Washer & dryer, towels, linens, complimentary toiletries, central air conditioning/heat, keyless entrybrFAQ: Stairs required for accessbrPARKING: Garage (2 vehicles), driveway (4 vehicles), RV/trailer parkingbrbr-- THE LOCATION --brbrOPT OUTSIDE: Plymouth City Park (3 miles), Firemans Park Elkhart Lake (6 miles), Rhine Center Bog State Natural Area (10 miles), Parnell Towers (12 miles), Kohler Arboretum (14 miles), Bookworm Gardens (17 miles)brATTRACTIONS: Cheese Capital of the World Arch (4 miles), Road America (5 miles), Wesley W. Jung Carriage Museum (8 miles), Sheboygan Marsh Tower (8 miles), Above & Beyond Children’s Museum (17 miles) brSKIING: Nutt Hill Ski Area (5 miles), Sunburst Ski Area (30 miles), Fox Hill Ski Area (39 miles), Little Switzerland Ski Area (43 miles)brAIRPORT: Wittman Regional Airport (46 miles), Appleton International Airport (67 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The property requires stairs to access

Bed

Bath

Sleeps

$842.64

/ Nightly

Private Vacation Home

Wisconsin Vacation Rental: 1 Mi to Road America!

Plymouth, Wisconsin, United States

Bring the whole family along for a fun-filled vacation in Plymouth, Wisconsin! This unique vacation rental home near Road America offers 5 bedrooms, 3 bathrooms, and a great location that gives you access to everything you want to do nearby. Spend your days at Road America, on Elkhart Lake, or exploring the attractions in Sheboygan, just a short drive away. In the evening, return to the spacious 26-acre property to stream your favorites or cook a delicious dinner in the kitchen!brbr-- THE PROPERTY --brbr3,500 Sq Ft | 26-Acre Property | 0.5 Mi to Downtown & Dining | Gas GrillbrbrBedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: King Bed | Bedroom 4: 2 Full Beds | Bedroom 5: Queen Bed | Basement Living Room: Queen Sleeper Sofa | Additional Sleeping: Pack ‘n Play, full-sized cribbrbrHOME HIGHLIGHTS: Fire pit (wood not provided), large backyard & property, covered deck, Smart TVs w/ cable, dining table, ceiling fans, furnished sunroom, multiple living roomsbrKITCHEN: Cooking basics, blender, coffee maker, dishwasher, Crockpot, stove/oven, refrigerator, microwave, dishware & flatware, ice maker, high chair, spices, toaster, toaster ovenbrGENERAL: Free WiFi, keyless entry, complimentary toiletries, linens & towels, in-unit washer & dryer, central air conditioning, baseboard heating, hair dryer, iron/board, laundry detergent, trash bags & paper towels brFAQ: 1 step required for entry, 3-story home brPARKING: Garage (2 vehicles), driveway (9 vehicles), RV/trailer parking available on-sitebrbr-- THE LOCATION --brbrMUST-DOS: Road America (1 mile), Quit Qui Oc Golf Club & Restaurant (2 miles), Wade House Historic Site (8 miles)brOPT OUTSIDE: La Budde Creek State Wildlife Area (1 mile), Little Elkhart Lake (2 miles), Firemans Park Elkhart Lake (2 miles), Ice Age Trail Greenbush Trailhead (5 miles), Sheboygan Marsh State Wildlife Area (7 miles), Kohler Park Dunes State Natural Area (24 miles)brDOWNTOWN SHEBOYGAN (18 miles): John Michael Kohler Arts Center, Bookworm Gardens, Deland Park, Above & Beyond Children's Museum, Sheboygan County Historical MuseumbrAIRPORT: Appleton International Airport (52 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: This property requires 1 step to enter and additional stairs to access the upper and lower levels

5

Bed

3

Bath

14

Sleeps

Vacation Home Rentals By Owner In Plymouth, WI

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$798.24

$288.01

$840.87

$231.59

$842.64

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