
House holiday rentals in Plymouth
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Top-rated house rentals in Plymouth
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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!

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

Stay at Sunrise LLC, Like being at Grandma's
Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural area, recreation trail head is 3 miles east of us as is the Wade House, 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. We do not have WIFI Phone reception for Internet is good. No Cable or Satellite TV, Over 32 antenna channels. Smoking is allowed outside of the home. No pets allowed.

House Near the Lake
Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

Vintage Farmhouse on Blueberry Hill.
Relax with the whole family at this peaceful place to stay. Located conveniently half way between Green Bay and Milwaukee. Find your self minutes away from Road America, Whistling Straits, snowmobile trails, kettle moraine state forest, and so much more. Our property has walking trails to the river, throughout the woods and around the creek area, This winter you would have the opportunity to snowshoe our 103 acre property, or break your own cross country ski trail! Or just a quiet getaway!

Oak Haven - Insane Game Room, Theater, Privacy
The search is over, you have found the PERFECT retreat at Oaks Haven! Experience the tranquility of nature surrounded by oak trees and birds. The luxury of a custom-built home (4,300 sq ft) thoughtfully designed for large groups to spread out or gather close. Or connect with friends over the expansive list of amenities including a 12-seat movie theater! The moment you pull in, you will become instant hero for planning the ultimate retreat. At Oaks Haven, we truly have thought of everything!

Spacious lower level priv entrance no cleaning fee
Not set up for babies or toddlers. Entire basement is for rent with a separate entrance. Kitchen area includes refrigerator, microwave, coffee pot, toaster, sink, dining table and chairs. NO STOVE OR OVEN IS AVAILABLE. Free Wifi and Cable TV. Air conditioning. Plenty of parking, keyless entry. 14 min to Road America, 13 min to Kohler, 9 min to Whistling Straits, 5 min to Lakeland University, 1 hr to Milwaukee, 1 hr to Green Bay. Lots of nice amenities, clean, spacious. No cleaning fee.

Modern Home Just 40 Minutes from GB NFL Draft
My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

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.

LUX Downtown Escape | Outdoor Movie Screen
Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

Woodland Creek Retreat: explore & relax!
Lovely home nestled in 9 acres of peaceful woodland. 1.5 miles off I-43. Enjoy a walk in the woods or enjoy the dunes and wonderful views of Lake Michigan from Terry Andrae State Park only .2 miles away! Enjoy relaxing on the front porch or taking in the view of the woods from the spacious back deck. Be on the lookout for turkeys and deer. Wonderful wood burning fireplace and extensive game collection(500+) for staying in! We love the cozy and open cabin feel and hope you will too!

Gleason's Chouse
You'll love staying in our unique home, in a quiet neighborhood. This is a recently remodeled 1867 church converted to a "Chouse". Featuring 2 bedrooms, Full Kitchen, 1 Bathroom, Balcony, Parking, and a Gazebo.. all beautifully complimented by a range of antiques and decorations. 8 Miles East of Hwy 41, a 45 min drive to Oshkosh or an hour to Milwaukee. Just down the from Lake Bernice & Eisenbahn Bike Trail. Also close enough to the Kettle Moraine Forest to hike and sightsee!
Popular amenities for Plymouth house rentals
House rentals with a pool

4 br 4.5 acre secluded country property

Hickory on the LakeWaterfront Luxury on Winnebago

Great EAA Location by the Airport

Close to EAA, pool, tennis/pickelball, pets ok

Private Home 4 BR+2Ba, Heated Pool by Road America

Cozy 4 bedroom home. Minutes to Eaa grounds.

Home Away From Home

5 BR Oshkosh Home: 7 ml to EAA/1 ml to Hwy 41
Weekly house rentals

The Suncatcher -Steps from Lake - Fenced Yard

Adorable bungalow in historic Sheboygan Falls,WI

Lake View Home Away From Home

Road America & Golf Retreat

The Hemisphere House

Paddock Point Lakehouse. Road America+Hot Tub

Fall and Holidays available! Long stays Welcome!

Hidden Haven - Modern Cottage w/ Hot Tub & Views
Private house rentals

Family friendly- rustic country living -king bed

Sleeps 7{SPACIOUS}Pets Welcome!

The Kohler House

Oma's Beach House

Racers golfers outdoor lovers we're ready for YOU!

Downtown. Sleeps 6 close to Road America

Fenced Yard; Waterfront; Dock, Cozy & Refreshing

Spacious Lakefront 3Br 3Ba Home
Quick stats about house rentals in Plymouth
Total rentals
30 properties
Nightly prices starting at
$91Â AUD before taxes and fees
Total number of reviews
2K reviews
Family-friendly rentals
30 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
Destinations to explore
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- Kohler-Andrae State Park
- Erin Hills Golf Course
- Whistling Straits Golf Course
- Harrington Beach State Park
- Milwaukee County Zoo
- West Bend Country Club
- Bradford Beach
- Trout Springs Winery
- Milwaukee Country Club
- The Bull at Pinehurst Farms Golf Course
- Discovery World
- Pine Hills Country Club
- Heiliger Huegel Ski Club
- Milwaukee Public Museum
- Pollock Community Water Park
- Sunburst
- Kerrigan Brothers Winery
- Vines & Rushes Winery
- Blue Mound Golf and Country Club
- Little Switzerland Ski Area
- Blackwolf Run Golf Course
- Parallel 44 Vineyard & Winery