9 properties  

$359-1,340/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.

We cannot wait to host you!

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$350-1,048/night

The Sandwood Cottage

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

Welcome to The Sandwood Cottage.

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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$395-1,383/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 cabin 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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$1,125-2,727/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.

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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$439-1,073/night

Old Trees Farm

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

Old Trees Farm Guesthouse 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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$127-346/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 condo. 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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$149-442/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 condo a Wave of Happiness.

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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$219-661/night

Orchard House Retreat

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

Welcome to Orchard House Retreat, 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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$149-342/night

Uptown Coach House

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

Welcome to the Uptown Coach House.

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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