Sheboygan Rentals
From $493 per night (USD)VRBO
Luxurious artistic 2 bed - 2 bath Condo; feel like living by the Coast!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
This is a very well-taken care of condo in the most touristic part of Sheboygan. Be close to two beaches, a pier walk, a ...
From $493 per night (USD)VRBO
From $252 per night (USD)Expedia
Modern South Pier Condo on Sheboygan River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped ...
From $252 per night (USD)Expedia
From $151 per night (USD)VRBO
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
About this space: Renovated 1930's home located in the historic downtown district within walking distance of breathtakin ...
From $151 per night (USD)VRBO
From $290 per night (USD)VRBO
N E W ! Cozy Corner Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Welcome to Cozy Corner Cottage by Great Lakes Getaways! Experience a home nestled in a serene neighborhood. The master ...
From $290 per night (USD)VRBO
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Studio 920 #5 - Cool Studio w\/ AC Monthly Rentals!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience comfort and style in our fully furnished 1-bedroom apartment, perfect for monthly stays. Relax in a cozy sett ...
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From $255 per night (USD)VRBO
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to King Park Beach House Deluxe! Experience the perfect family getaway where breathtaking lake views and family ...
From $255 per night (USD)VRBO
From $272 per night (USD)VRBO
Riverwalk Retreat - Overlooking Sheboygan River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Riverwalk Retreat by by Great Lakes Getaways! Discover the ultimate retreat in this top-floor Riverfront con ...
From $272 per night (USD)VRBO
From $70 per night (USD)VRBO
NEW! Crystal Cove - Lux Lakefront Condo w\/ Massage Chair. Walk to Lake Michigan!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to Crystal Cove by Great Lakes Getaways! Nestled along the picturesque South Pier in Sheboygan, where beachfron ...
From $70 per night (USD)VRBO
From $182 per night (USD)VRBO
LUX Uptown Escape - The Trester\n
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers ...
From $182 per night (USD)VRBO
From $344 per night (USD)Expedia
Riverfront Townhome with Breathtaking Water Views!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
*exterior fire table cannot be used after october 1. Welcome to Driftwood, our modern two-bedroom, 1.5-bath townhome, n ...
From $344 per night (USD)Expedia
From $259 per night (USD)VRBO
Centrally located house minutes away from the lake, golfing, & Road America.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Get cozy on the big covered front porch by enjoying a cup of coffee or a local brew. Relax with a book or glass of wine ...
From $259 per night (USD)VRBO
From $563 per night (USD)Expedia
Simply Stunning Family Style W\/ 6 Pools
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Summary: Direct Ocean Front Condo with beach access Family Style with oversized sectional couch and 64" Smart Tv 3 Bedro ...
From $563 per night (USD)Expedia
From $375 per night (USD)VRBO
Perfect Paradise : Luxury Beachfront Condo!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Perfect Paradise by Great Lakes Getaways! Explore your dream destination in this stunning 4-bedroom beachfro ...
From $375 per night (USD)VRBO
From $258 per night (USD)VRBO
Wonderful 3+ Bedroom Home Completely Renovated
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. Three entire floors of space fo ...
From $258 per night (USD)VRBO
From $293 per night (USD)VRBO
Newly Updated! Downtown & Shore
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $293 per night (USD)VRBO
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Conveniently located in beautiful Sheboygan!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 90
Comfy Bungalow with baby grabs piano. An artists get-away. Cook in the nice kitchen with everything you need or walk to ...
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Perfect location for Ryder Cup!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Tri-level home in a quiet neighborhood with modern updates and less than five miles from the Ryder Cup! Perfect backyard ...
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From $161 per night (USD)Expedia
BEACHSIDE GETAWAY IN SHEBOYGAN
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located just one lot in from the beautiful shores or Lake Michigan. This amazing location provides year round stunning v ...
From $161 per night (USD)Expedia
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Modern Cabin, private wooded lot with lake access
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly renovated home with grilling deck and fire pit. 600 foot walk to the beach. Brand new Kohler bathrooms, electric f ...
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From $1206 per night (USD)Expedia
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Escape to your own private Lakeside Retreat. 4 BR, 2.5 bath Cape Cod overlooking Lake Michigan & Black River giving you ...
From $1206 per night (USD)Expedia
From $217 per night (USD)VRBO
Adorable cape cod with views of Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Adorable Cape Cod in Sheboygan near Lake Michigan. Located near Vollrath Park and North Beach Overlook and North Point B ...
From $217 per night (USD)VRBO
From $253 per night (USD)Expedia
Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Indulge in a fun-filled getaway when you stay at this 2-bed, 1-bath Wisconsin vacation rental! Boasting a colorful open ...
From $253 per night (USD)Expedia
From $1988 per night (USD)VRBO
Start planning now for the holidays-neutral spot to celebrate with family!
- Bedrooms:
- 9
- Bathrooms:
- 10
- Sleeps:
- 24
The 10,000 square foot Castino Lakeview Mansion sits high atop a bluff with uninterrupted breathtaking views of Lake Mic ...
From $1988 per night (USD)VRBO
From $1504 per night (USD)VRBO
Quiet and spacious home, close to downtown, the beach, and fantastic golfing.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled on a wooded acre in a quiet cul de sac. The cozy wood burning fireplace and wet bar in the family room is great ...
From $1504 per night (USD)VRBO
From $185 per night (USD)VRBO
Seagull Beach Guest House, Lake Michigan Cottage On Private Beach
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
The whimsical little cottage has a spectacular view of the private beach, the woods and sunrises. Starting right at your ...
From $185 per night (USD)VRBO
From $973 per night (USD)VRBO
Whistling Straights 4 min, Blackwolf Run 7 min, Erin Hills 84 min, 3 Bedroom
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Two Story Home With 3 Bedrooms, 2-1/2 Bathrooms, Large Kitchen, Dinette, Formal Dining Room, Living Room, Family Room, ...
From $973 per night (USD)VRBO
From $616 per night (USD)VRBO
Luxury Lake Front Villa: Sleeps 14!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Get ready to relax in this 4-bedroom townhome in Sheboygan. This amazing property features 1 king bed, 3 queen beds, and ...
From $616 per night (USD)VRBO
From $177 per night (USD)Expedia
Downtown Beachside Condo with Lake Michigan Views
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
You will see & hear the beauty of Lake Michigan during your stay at this main floor condo. A deck to the north allows ...
From $177 per night (USD)Expedia
From $445 per night (USD)VRBO
Charming 4-bedroom house with WiFi and AC in lovely Sheboygan
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
Located in Sheboygan, this fabulous house boasts 4 bedrooms with 3 queen beds and 1 king bed. With 4 bathrooms including ...
From $445 per night (USD)VRBO
From $605 per night (USD)VRBO
Lake Michigan Beach Retreat with Treehouse
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
Ideal for traveling families, remote workers, lake lovers, and golf enthusiasts, this peaceful, woodsy retreat is steps ...
From $605 per night (USD)VRBO
From $551 per night (USD)VRBO
The Kohler House
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
The Kohler House is located in the quaint village of Kohler. Our family grew up in this neighborhood and created a spac ...
From $551 per night (USD)VRBO
From $266 per night (USD)VRBO
Lighthouse Lookout - Views of Lake and River!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Lighthouse Lookout by Great Lakes Getaways! Discover the ultimate retreat at Sheboygan's Riverfront condo wi ...
From $266 per night (USD)VRBO
From $375 per night (USD)VRBO
Across from Kohler-Andrae w\/ Orchard Style Yard & Pavilion
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Orchard House Retreat, situated directly across from the picturesque Kohler-Andrae State Park and the scenic ...
From $375 per night (USD)VRBO
From $228 per night (USD)Expedia
Cozy and charming country estate less than 5 minutes from Whistling Straits!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful 3 bd, 2 bath Country Estate nestled among a variety of mature trees in the town on Mosel, WI. Within a 10-minu ...
From $228 per night (USD)Expedia
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Spacious Blue Harbor 2 bedr courtyard view condo w\/ Breaker Bay Waterpark access
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Detach yourself from the main crowd and check yourself into the 1242 square feet of spacious privacy of your own lakesid ...
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From $794 per night (USD)Expedia
Fairway Getaway-by Whistling Straits, Golf sim\/Theater Room, ZenDen &Poker Room!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $794 per night (USD)Expedia
From $289 per night (USD)VRBO
The Cottage at Beachfront Lane!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to The Cottage by Great Lakes Getaways! Escape to this newly renovated beachfront condo nestled along the seren ...
From $289 per night (USD)VRBO
From $340 per night (USD)VRBO
Private, Mid Century Modern, Panoramic Views, Newly Furnished
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Peaceful and private getaway in the woods, yet close to everything! Shops, restaurants, bars, parks, golf, fishing, sail ...
From $340 per night (USD)VRBO
From $264 per night (USD)VRBO
Sheboygan Retreat in Black River
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Only an hour drive north of Milwaukee and south of Green Bay. Experience all Sheboygan County has to offer. Kohler gol ...
From $264 per night (USD)VRBO
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Cottage in the Woods walk to Lake Michigan!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Cottage in the black river area of Sheboygan County. Located on almost and acre of wooded property two blocks from publ ...
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