Holiday houses in Plymouth

4.99 out of 5 average rating, 358 reviews

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

Cabin in Elkhart Lake

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.

ValueLocationLayout

The kitchen features dark cabinetry with artistic landscape designs and a large white countertop island. Stainless steel appliances include a stove and dishwasher, while a coffee maker is positioned on the counter. Natural light enters through a nearby doorway, illuminating the warm wood tones of the floor.

4.97 out of 5 average rating, 206 reviews

The 2400 sq ft Plymouth Paddock near Road America!

This charming two story, 2400 square ft colonial house is the perfect respite for families looking to connect, or race fans looking for a home during race weekend. Only 4 miles from Road America the location is close to all of Sheboygan County's finest attractions. Located two blocks from downtown on a quiet street, its up to you how you want to spend your evening. You could walk downtown for a bite, have a campfire, make a meal, or just spend time together. Welcome to your home away from home!

ValueLocationTV

4.93 out of 5 average rating, 300 reviews

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

FamilyLocationBackyard

5.0 out of 5 average rating, 52 reviews

A spacious living area is observed, featuring a comfortable gray sofa and a coffee table resting on a light rug. Bright windows allow natural light to illuminate the room. A television is positioned on a media console, along with a small dining table and chair set against the wall.

Guest suite in Plymouth

Downtown Plymouth, WI Second Floor 2 Bed Apartment

Second floor apt. with two single bedrooms, a queen bed and a full bed in the other. Full bath, kitchen, living room, outdoor smoke deck, long driveway for parking (first 3 feet of the driveway are steep). Enjoy a short walk to many shops and restaurants or check out the wall murals in the Cheese Capital of the World! You don’t have to travel too far for excitement Road America (4.5 mi), Plymouth Dirt Track (1.1 mi), Whistling Straits Golf Course (20.5 mi) Kettle Moraine nature trails 20.4 mi

FamilyLocationDecor

Place to stay in Plymouth

A charming two-story farmhouse features a welcoming front porch with two chairs and is flanked by neatly landscaped greenery. An adjacent garage with large windows enhances the property's charm. The overall setting is surrounded by lush trees, creating a serene rural atmosphere.

4.98 out of 5 average rating, 108 reviews

The Loft at Hickory Haven-A Modern Rural Studio

The Loft at Hickory Haven is a modern country retreat made for two! Mary & Bob constructed The Loft studio in 2020 and filled it with the modern traveler's amenity wish list: A comfy king bed, central AC, a gas-fired stove, a modern bathroom, and a kitchenette with dining area. The property's rural setting offers a peaceful haven from your daily grind. Your day will start with the chirping of birds or a wild turkey sighting and end with a star-filled sky that is a site to behold! Welcome!

ValueLocationBathroom

4.94 out of 5 average rating, 32 reviews

A deck furnished with wooden chairs offers a view of the reflective lake surrounded by vibrant autumn foliage. Colorful trees frame the water, enhancing the natural setting. Tables and seating are visible in the open space below, providing areas for gathering.

Cabin in Plymouth

Walking distance to Road America, Lakefront

Nestled in the woods, you will find fun for the whole family. Our Little Elkhart lakefront cottage has two bedrooms that can easily sleep six guest. We offer kayacking, biking, swimming, an outdoor fire pit, two decks overlooking the lake, and highspeed internet service. This cottage sits on 3/4 acres less than 1 mile from Road America, 4 miles from downtown Elkhart Lake, and several beautiful golf courses. It has all of the amenities for your memorable family vacation. Sorry no pets.

LocationFamilyView

Superhost

5.0 out of 5 average rating, 3 reviews

Escape from the Track - Massage Chair | Fire Pit!

🏁 Escape the Track & Relax in Style! Just minutes from Elkhart Lake, this spacious Plymouth retreat is perfect for race weekends, family getaways, and group trips. Featuring 3 bedrooms, 2 baths, massage chair, Kohler bathroom with soaking tub, huge fully equipped kitchen, fire pit, multiple TVs, 2 stand-up arcade games, and a classic Nintendo system. Plenty of room for everyone to unwind after a day of adventure while enjoying all the attractions Plymouth and Elkhart Lake have to offer!

LocationFamilyLayout

5.0 out of 5 average rating, 275 reviews

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!

LocationValueSleep quality

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

4.88 out of 5 average rating, 56 reviews

Lake Front Cottage With Dock. Walk to Road America

Do you like tranquil, peaceful and serene? Don’t miss out on our lake front house. Huge windows with lake views and lots of natural light. Walking distance to Road America. Relax by our outdoor fire pit. Fish or kayak off or dock or swim within 900 ft of the driveway. Enjoy our game room with Pac-man video console or play corn hole. Quiet and relaxing but minutes to the Kettle trails and Historic downtown Elkhart Lake.

ValueFamilyOutdoor spaces

Apartment in Campbellsport

A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.

4.97 out of 5 average rating, 112 reviews

GGG Spacious Log Cabin apartment on the IAT

With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated with new floors, paint, fixtures and more, it’s a perfect retreat from the city. Explore the adjoining 500 acres of state forest, with public lake and boat launch across the street for fishing and paddling. The adjacent trail leads right the Parnell Segment of the Ice Age trail and Mauthe Lake State Park.

LocationFamilyCondition

Place to stay in Plymouth

A three-story building features a combination of wooden and stone exteriors. Bright windows adorn the upper floors, while a spacious deck is visible on the second level. Lush greenery and blooming flowers surround the base, creating a serene outdoor setting.

4.97 out of 5 average rating, 72 reviews

Crystal Sunset Loft - Elkhart Lake

Beautiful views, beautiful space – Crystal Sunset Loft is THE place to relax if you are looking for a quiet and scenic refuge after a day at the track or hiking through the kettles. Only a mile away from Road America’s main gate, Elkhart Lake, and the village’s fun nightclub scene, this is the perfect setting for your weekend or mid-week getaway.

LocationValueSleep quality

4.83 out of 5 average rating, 124 reviews

Two Adirondack chairs are positioned along the water's edge, surrounded by trees and greenery. A tree-mounted birdhouse is visible nearby. The scene reflects a tranquil setting by the blue waters, enhancing the natural surroundings.

Guest suite in Plymouth

De' Udder Place on the Water

Lower level of my home on the water. Just 5 miles from Road America and 19 miles from Whistling Straits. Close to Kohler, Elkhart Lake, Lake Michigan, and the Kettle Moraine State Forest. After a day out in Sheboygan County, return to your guest suite and enjoy a cocktail in your private sunroom or in an Adirondack chair at the water's edge.

LocationValueParks

Popular amenities for Plymouth holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Plymouth

5.0 out of 5 average rating, 23 reviews

Home in Sheboygan

Sunset Vista- cozy two bedroom retreat

LocationFamilyView

4.92 out of 5 average rating, 74 reviews

A serene bedroom is furnished with a spacious bed adorned with decorative pillows. Large glass doors open to a private balcony, while a comfortable armchair and a small tabletop are positioned near the window, allowing natural light to fill the room.

Home in Sheboygan

Sheboygan Riverside Condo

LocationValueParking

5.0 out of 5 average rating, 11 reviews

Home in Cleveland

Shoreline Serenity

LocationValueOutdoor spaces

The exterior of a two-story house is showcased, featuring a light-colored facade and a spacious deck. The driveway is bordered by vibrant purple flowers and lush greenery, contributing to the welcoming atmosphere. A garage is visible, enhancing the home's functionality.

4.9 out of 5 average rating, 42 reviews

Kettle Breeze

LocationFamilyKitchen

5.0 out of 5 average rating, 36 reviews

An open studio space features a comfortable king bed with blue bedding and a modern wooden frame. A gray pull-out couch is positioned nearby, alongside a stylish lamp on a side table. A decorative area rug covers the floor, adding a touch of warmth to the minimalistic decor.

Apartment in Plymouth

Spacious Studio Apt walking distance to RD America

ValueLocationWalkability

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

Apartment in Plymouth

4.64 out of 5 average rating, 367 reviews

Pineyard Plymouth Apartment

ValueFamilyCheck-in

4.96 out of 5 average rating, 256 reviews

A tree-lined pathway leads to a cozy cottage, framed by colorful fall foliage. Orange pumpkins are placed near vibrant purple flowers, enhancing the seasonal charm. The yard is spacious, surrounded by mature trees, providing a serene and inviting atmosphere.

Cottage in Elkhart Lake

Schoolhouse cottage

LocationFamilyDecor

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