Sheboygan Vacation Rentals

Looking for a vacation home in Sheboygan County, Wisconsin? From spacious beachfront townhouses to cozy cabins with a hot tub or firepit, you’re sure to find a perfect base for your Sheboygan adventure in our collection of stunning properties.

Nestled on the shores of Lake Michigan, Sheboygan is an idyllic vacation destination offering stunning beaches, a vibrant arts scene, and an abundance of outdoor activities. The area is known as the “Malibu of the Midwest” for its excellent surfing conditions, and it’s a perfect paradise for visitors who want to golf, fish, and explore the scenic Kohler-Andrae State Park.

Many of our lakefront properties offer unobstructed lake views from their private decks, where your group can enjoy a peaceful morning coffee or an evening glass of wine. Or, outdoorsy hikers can opt for a pet-friendly cabin surrounded by natural beauty with trails starting directly from their doorsteps.

Are you more of a foodie, art lover, or retail therapy enthusiast? Our downtown Sheboygan properties are ideal for vacationers who want to be close to the city’s best restaurants, galleries, and stores.

Choosing to stay in a vacation rental over a hotel gives your party a comfortable home-away-from-home experience with more space, privacy, and amenities. This makes it a top choice for families and multi-generational families, couples, and groups of friends looking for a place to relax and unwind.

Ready to experience everything that this charming city has to offer? Book your Sheboygan vacation rental today to experience a fun and relaxing getaway that you’ll never forget.

14 properties  

$289-1,519/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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$189-1,559/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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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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$649-3,944/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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$289-1,609/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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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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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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$219-889/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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$119-489/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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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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$239-1,239/night

Nelly's Place

3 Bedrooms • Sleeps 1-8
Internet Wood Stove Beachfront

***Beach is a 30-second walk, NOT an 11-minute walk. We own 100’ of pristine private beach and Lake Michigan access that the cabin sits on. ***

Enjoy a memorable escape on the beach AND in the woods at your private luxury cabin on Lake Michigan's beachfront. Feels like the North Woods, but is just 45 min north of Milwaukee.

Unique to the area is this special cabin surrounded by woods with a sandy beach for those who like days on the shore, making fireside memories, stargazing, walks, and fun surrounded by nature's best. Many activity options in the huge, grassy yard (basketball, old-fashioned play equipment, fire pits...)!

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$289-999/night

The Pond Cottage

2 Bedrooms • 1 Bath • Sleeps 1-7
Internet Fireplace Beachfront

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

Beautifully updated and redecorated in 2025, our cottage is 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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