House holiday rentals in Elkhart Lake

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, 200 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!

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Superhost

Home in Cleveland

5 out of 5 average rating, 4 reviews

Shoreline Serenity

Welcome to ''Shoreline Serenity''! 200 ft of Lake Michigan frontage w/unobstructed views that go on for miles and tucked away on a 2-acre lot offering peace & privacy. Inside the home, you will be drawn to the beautiful views through the full wall of east facing windows & patio doors. The interior is cozy, clean, and comfortable. Fully equipped kitchen w/coffee bar. Main level has (2) bedrooms including the primary bedroom w/fantastic views. The spacious upper level loft has a king & twin bed.

ComfortAmenitiesView

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.

4.92 out of 5 average rating, 293 reviews

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

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4.96 out of 5 average rating, 199 reviews

A single-story house with a neatly maintained lawn and vibrant flower beds welcomes visitors. An American flag is displayed at the entrance. The driveway leads to a garage on the left side of the house, and ample green space surrounds the property.

Home in Howards Grove

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.

FamilyValueParks

An inviting wellness space features a hot tub with gentle bubbles and soft green lighting. Adjacent, a wooden dry sauna awaits, surrounded by potted plants. Comfortable seating with decorative pillows is arranged nearby, creating a serene atmosphere for relaxation.

4.98 out of 5 average rating, 268 reviews

Boutique Wellness Retreat - Hot Tub and Fireplace

Celebrate your special occasion in Sheboygan at this beautiful boutique home. New patio and deck! Hot tub/Dry Sauna! Comfort and charm throughout. Cooks kitchen with all amenities. Primary bedroom w/King size bed. Secondary bedroom has 2 twin beds. The beautiful fireplace in the living room is perfect for a relaxing couples evening. Enjoy a glass of wine or local brew on the patio while you grill out. EV Charger and E-Bikes to explore the area. Let us impress you and help make it a memory.

LocationFamilyHot tub

4.92 out of 5 average rating, 115 reviews

A historic lighthouse stands at the water's edge, illuminated by the vibrant colors of sunset. Smooth stones line the shoreline, reflecting the serene lake. Lush greenery is visible in the background, creating a peaceful coastal setting.

Home in Fond du Lac

Woltring Waters Waterfront Home + Hot Tub

Wake up to a beautiful view of Lake Winnebago, and enjoy you cup of coffee with the sound of crashing waves off the back porch. You will have breathtaking sunsets with the historical light house backdrop that is in viewing distance from the property. From dining to convenient stores everything you need is in walking distance. Take a peaceful stroll around the marina or take the kids to Lakeside Park, offering a petting zoo, carousel, train, jungle gym & splash pad. Everyone will enjoy!

FamilyValueLaundry

4.96 out of 5 average rating, 178 reviews

An aerial view of a spacious home is surrounded by mature trees, showcasing a private sandy beach alongside Lake Michigan. The property features a pathway leading to the house, emphasizing its secluded setting amid natural greenery.

Home in Oostburg

Lake Michigan Beach Home by Frank Lloyd Wright pro

Beautiful view and sand beach on Lake Michigan, completely private, surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room, and living room entertainment space, den with a see-through log-fired fireplace, screened-in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and a row boat are available for the boating enthusiast, with life jackets and other floating devices.

ValueFamilyOutdoor spaces

4.95 out of 5 average rating, 189 reviews

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.

ValueLocationAir conditioning

The exterior of a charming Cape Cod-style house is shown, featuring a sloped roof and welcoming porch. Lush green lawns surround the property, complemented by a variety of plants and trees. Large windows allow for natural light, creating an inviting atmosphere.

5 out of 5 average rating, 20 reviews

The Finish Line

Our cozy refurbished Cape Cod getaway is just steps from the downtown action, but offers a quiet respite at the end of the day. Enjoy the comfortable beds, fully appointed kitchen, fireplace, BBQ grill, onsite parking, outdoor patio, and big back yard. Walk to downtown restaurants and attractions, the Osthoff Resort, the Throttlestop, and beautiful Elkhart Lake, all just blocks away. About one hour from Lambeau Field, Milwaukee, or EAA. The Finish Line is your home away from home.

LocationCleanlinessHospitality

4.95 out of 5 average rating, 174 reviews

Oak Haven | Theater • Game Room • Sauna • Firepit

Welcome to Oak Haven, a private 4,300 sq ft retreat surrounded by oak trees and peaceful Wisconsin beauty. 🌿 • 12-seat movie theater with plush recliners & surround sound 🎬 • Game room with pool, ping pong, shuffleboard & poker 🎱 • Infrared sauna + two outdoor fire spots for perfect nights 🔥 • Gourmet kitchen & dining for twelve 🍽️ • Minutes to Kohler golf, Kettle Moraine & Road America 🏎️ ✨ Oak Haven—where relaxation, laughter, and connection come naturally.

ValueFamilyWi-Fi

A charming two-story home is showcased with a welcoming porch and well-maintained landscaping. Green grass surrounds the house, and colorful flowers add vibrant touches along the walkways. The building's exterior is finished in gray vinyl siding, complemented by white window trim and a sloped roof.

4.97 out of 5 average rating, 33 reviews

Downtown. Sleeps 6 close to Road America

Welcome to our cherished family home, nestled in the heart of a magical town that holds countless memories for us. We're two sisters and our husbands, joined by our six kids, all deeply connected to this special place. Together, we've decided to keep this legacy alive and invite others to experience the charm and warmth of our beloved hometown. It's your turn to make new memories while enjoying the beauty and magic that has captivated our family for generations.

ValueLocationWalkability

4.96 out of 5 average rating, 157 reviews

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

Guest Favorite | Super Host + Clean & Modern Stay!

Unwind in this modern retreat just minutes from Whistling Straits Golf, Road America, Lake Michigan, and year-round outdoor adventures. The bright, open living spaces feature high ceilings, skylights, and stylish furnishings, with thoughtful comforts like heated bathroom floors. Enjoy the spacious outdoor living area for relaxing after a day out. Ideal for golfers, couples, families, wedding groups, business travelers, and traveling nurses.

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Popular amenities for Elkhart Lake house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A spacious country home is set back amidst tall trees and a green yard. A circular driveway leads to the entrance, featuring a large garage and a basketball hoop. Sunlight filters through the leaves, creating a serene outdoor atmosphere.

Home in Fond du Lac

4.9 out of 5 average rating, 10 reviews

4 br 4.5 acre secluded country property

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Superhost

4.64 out of 5 average rating, 14 reviews

New place to stay

Lake Views | Walk Everywhere | 3BR Beach Resort

The exterior of a charming single-story home is visible, featuring a well-maintained lawn with neatly trimmed hedges. A stone pathway leads to the entrance, which is flanked by decorative planters. A spacious driveway provides access to an attached garage.

Home in Oshkosh

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

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An outdoor area features a heated swimming pool filled with clear blue water, surrounded by a spacious deck. A wooden pavilion with seating is positioned nearby, offering shade and a place to relax. Poolside lounge chairs are arranged for sunbathing.

4.96 out of 5 average rating, 48 reviews

Road America Retreat-4 BDRM-2BA-Hot Tub+Pool

FamilyLocationAmenities

5 out of 5 average rating, 3 reviews

New place to stay

Luxury Pool Retreat-2 Acres-Near Whistling Straits

ViewIndoor spacesHospitality

A well-maintained home is displayed, featuring a light-colored exterior and a welcoming porch with green railings. An American flag is flown proudly in the front yard. The two-car garage is visible, with a driveway that leads to the entrance and accessible landscaping.

Home in Oshkosh

3 Bedroom, 2 Bath House, Available during EAA only

LocationNearbyAccuracy

4.91 out of 5 average rating, 34 reviews

An indoor heated pool is framed by light-colored walls adorned with subtle marine-themed decor. Smooth tiles line the edge of the pool, while several white chairs are arranged nearby. Natural light filters through windows, reflecting on the calm water.

Home in Two Rivers

Cool City, Warm Pool

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A spacious living area features a large, dark gray sectional sofa with decorative pillows, set on a patterned area rug. A small side table is positioned nearby, and natural light filters in through sheer curtains covering a window. The walls are adorned with a 'HOME' sign.

Home in Oshkosh

4.5 out of 5 average rating, 4 reviews

Cozy 4 bedroom home. Minutes to Eaa grounds.

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Weekly house rentals

A spacious living area features a stone fireplace beneath a wall-mounted TV. A wooden coffee table is positioned on a dark hardwood floor, with a cozy red throw draped over a light-toned couch. Soft lighting is provided by track lights on the ceiling.

5 out of 5 average rating, 13 reviews

Racers Haven - 1 min from Road America

LocationComfortWalkability

The exterior view of the home presents a combination of stone and wood siding, accentuated by large windows that showcase the scenic surroundings. A pathway of stepping stones leads to a covered porch, framed by well-maintained grass and nearby trees.

4.77 out of 5 average rating, 31 reviews

Summit Ranch - Elkhart Lake/Road America- 3 mins

LocationCheck-inAccess

The exterior of a two-story home is displayed, surrounded by a lush green landscape. A stone-lined driveway leads to the entrance, featuring stairs that ascend towards the front door. The home’s siding is a muted green, and a black grill is visible on the upper deck.

4.92 out of 5 average rating, 25 reviews

Turn 15 Lodge near Road America

FamilyLocationGetting around

5 out of 5 average rating, 33 reviews

The exterior of the property is framed by lush greenery and colorful flowering plants. A rustic wooden fence runs along the foreground, while the house is partially obscured by trees, creating a serene and inviting environment.

Home in Kiel

Kiel River House

FamilyLocationCleanliness

A sunlit sunroom features a cozy seating arrangement with two wicker armchairs and a spacious sofa adorned with blue and white cushions. Large windows provide multiple views of the surrounding greenery and the lake, allowing natural light to fill the space.

5 out of 5 average rating, 13 reviews

Lake House-Kayaks/Paddle Boards/Private Pier

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5 out of 5 average rating, 38 reviews

Family Cottage, Walk to the lake (pet friendly)

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A modern kitchen features stainless steel appliances and marble countertops. Natural light streams through large windows, illuminating the space. Four bar height stools are positioned along a counter, inviting a casual dining experience. Exposed wooden beams add a touch of warmth to the design.

5 out of 5 average rating, 10 reviews

Stylish Ranch Near Road America

LocationSleep qualityBathroom

A spacious living area features soft seating, including a comfortable sofa adorned with decorative pillows. Natural light filters through sheer curtains, illuminating the light wood flooring and accent rug. A grouping of framed artworks and a stylish chandelier enhance the inviting atmosphere.

5 out of 5 average rating, 15 reviews

Elkhart Lake Getaway-Walk to Town + Lake!

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Private house rentals

5 out of 5 average rating, 15 reviews

Sunset Vista- cozy two bedroom retreat

LocationFamilyTV

5 out of 5 average rating, 46 reviews

A wooden deck equipped with a large dining table surrounded by six matching chairs faces the serene expanse of Lake Michigan. An umbrella is positioned to provide shade, and the bright blue sky enhances the view of the calm water.

Home in Oostburg

Lakefront Blue Dune Cottage on Lake Michigan.

FamilyLocationCheck-in

5 out of 5 average rating, 36 reviews

Farm Fresh Eggs, Amazing Outdoor Space w/ Fire Pit

LocationFamilyNearby

5 out of 5 average rating, 7 reviews

3 Minutes to Road America | Amazing Location!

LocationAccessIndoor spaces

5 out of 5 average rating, 62 reviews

A serene lakeside view features a setting sun casting warm hues over the water. A grassy area with neatly arranged seating faces the lake, while two trees provide a natural frame. Smooth stones and a pathway lead towards the water's edge.

Home in Fond du Lac

Spacious Lakefront 3Br 3Ba Home

LocationFamilyOutdoor spaces

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.

4.91 out of 5 average rating, 68 reviews

Sheboygan Riverside Condo

LocationFamilyQuiet

5 out of 5 average rating, 39 reviews

The Woods Estate walk to RoadAmerica modern luxury

ValueLocationAccess

The exterior of the house features a white facade, complemented by a welcoming front porch with a green chair. A lamp post stands nearby, and potted flowers adorn the porch. Lush greenery and a gravel path lead to the entrance, creating an inviting approach.