12 properties  

$199-3,789/night

Pine Dunes Cabin

4 Bedrooms • 3 Baths • Sleeps 7-10
Internet Wood Stove Beach Hot Tub

Whether you are looking to decompress at the beach, or spend your day enjoying one of the world-class golf courses, hiking or biking Kohler Andrae State Park, a day at Road America, or a fishing charter on Lake Michigan, you can rest comfortably in the modern rustic style of Pine Dunes Cabin hosted by Sheboygan Vacation Rentals.

We cannot wait to host you!

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$239-3,750/night

The Sandwood Cottage

4 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 7-10
Internet Firewood Provided Beach

Welcome to The Sandwood Cottage hosted by Sheboygan Vacation Rentals.

Family and friends are everything. When we set out to put this home together, we wanted to be sure it was perfectly suited for gathering, conversation, fun and most importantly, making memories.

Newly remodeled in 2023, and professionally designed by the well-known Jordan Gottsacker of Honey and Ace, The Sandwood Cottage will help you relax, unwind, and strengthen those familial bonds and friendships.

We cannot wait to host you!

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$329-4,239/night

The Big Montana at Elkhart Lodge

7 Bedrooms • 3 Baths • Sleeps 11-18
Allows pets Internet Fireplace
Experience rustic charm in our "Big Montana" Log Cabin located at Elkhart Lodge. The Big Montana cabin, hosted by Sheboygan Vacation Rentals, sits on 5 acres near Road America and Elkhart Lake Beach, comfortably sleeps 18 with 7 bedrooms, 3 bathrooms and is ideal for groups. Fully loaded kitchen, cozy living areas, outdoor deck. Great proximity to the racetrack and lakeside relaxation. Book now for an unforgettable getaway!

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$394-7,124/night

The House at Wilson Shore

6 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 11-15
Internet Fireplace Beachfront

Welcome to the House at Wilson Shore hosted by Sheboygan Vacation Rentals.

Escape to the serene beauty of this stunning lakefront vacation rental, situated right on Lake Michigan and just moments away from Kohler, Sheboygan, and Kohler-Andrae State Park. Nestled on a tranquil waterfront setting, this property boasts spectacular views, a private beach, and the peace and quiet you've been searching for.

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$289-3,119/night

Old Trees Farm

5 Bedrooms • 3 Baths • Sleeps 1-12
Internet Fireplace

Old Trees Farm Guesthouse, hosted by Sheboygan Vacation Rentals, Welcomes You!

​Your Home Away From Home

Visit the friendly resident farm animals, relax under the old black oak tree or enjoy a cozy fire after a long day of exploring the many diverse activities Sheboygan County has to offer.

We have thought through every amenity to make sure each guest (regardless of age) has a remarkable experience at Old Trees Farm.

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$119-1,329/night

Waves of Happiness Lower Condo

2 Bedrooms • 1 Bath • Sleeps 2-4
Internet Fireplace Beach View

You will see & hear the beauty of Lake Michigan during your stay at this main floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals.

A deck to the north allows views of the magnificent Blue Harbor Resort. The south deck gives more amazing views of the lake, plus a park just steps out the back door. You can stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art, & exquisite restaurants - walkable from the condo.

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$119-1,249/night

Waves of Happiness Upper Condo

2 Bedrooms • 1 Bath • Sleeps 4-5
Internet Fireplace Beachfront

Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan Vacation Rentals.

You just decide whether to sit on the north or south deck to enjoy the sights and sounds of Lake Michigan. Less than 200 feet to the beach and a sprawling city park for our backyard. Plan to stroll the beach, walk the River Boardwalk, or tour our historical downtown full of shops, art opportunities, & exquisite restaurants--WALKABLE from the condo.

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$219-2,589/night

Orchard House Retreat

4 Bedrooms • 4 Baths • Sleeps 5-8
Internet Fireplace

Welcome to Orchard House Retreat, hosted by Sheboygan Vacation Rentals. Our home is situated directly across from the picturesque Kohler-Andrae State Park and the scenic Black River Trails.

Our retreat is charming and character-filled and offers the perfect blend of natural beauty and cozy comfort.

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$129-1,329/night

Uptown Coach House

2 Bedrooms • 1 Bath • Sleeps 1-4
Internet Downtown

Welcome to the Uptown Coach House hosted, by Sheboygan Vacation Rentals.

Our newly built coach house is nestled in the heart of downtown Sheboygan near all the action and some of our finest dining options. You will also find our most Fabulous "North Beach" to be just a 1/2 mile away.

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$139-1,949/night

Rose & Fern's Delightful Seaside Picnic

3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 4-8
Internet Fireplace Beachfront

Welcome to our "Delightful Seaside Picnic," hosted by Rose and Fern and Sheboygan Vacation Rentals!

This newly renovated home offers a serene retreat just steps from Sheboygan’s stunning shoreline where you can enjoy a sunrise stroll along the sandy beach or a refreshing dip in the lake.

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$349-5,709/night

Nelly's Place

3 Bedrooms • Sleeps 1-8
Internet Wood Stove Beachfront

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$439-4,489/night

The Pond Cottage

2 Bedrooms • Sleeps 1-7
Internet Fireplace Beachfront

Welcome to The Pond Cottage, hosted by Sheboygan Vacation Rentals!

Nestled atop a scenic dune along the shores of Lake Michigan, The Pond Cottage offers the perfect blend of tranquility and adventure. Whether you’re seeking a peaceful escape or looking to explore the cultural and recreational treasures of Kohler and Sheboygan, this private, pristine getaway has it all.

Wake up to breathtaking, unobstructed views of the lake from the moment you step inside, and enjoy 275 feet of stunning private lakeshore frontage.


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