Sheboygan Rentals
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Shoreline Sanctuary - 4BR Villa w/ Lake Views, Beach Access & Sunsets
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Shoreline Sanctuary by Great Lakes Getaways! This stunning 4-bedroom, 3-bathroom beachfront villa on Lake Michigan offe ...
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From $309 per night (USD)Expedia
Wandering Waves - Beachfront condo right on Lake Michigan.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Wandering Waves by Great Lakes Getaways! Enjoy breathtaking Lake Michigan views from this updated 2-bedroom, 2-bathroom ...
From $309 per night (USD)Expedia
From $273 per night (USD)VRBO
Cozy Corner Cottage- 2 blocks to Lake Michigan. Walk to Deland Park and Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Cozy Corner Cottage by Great Lakes Getaways! This charming Dutch Colonial house in Sheboygan’s historic Ellis District ...
From $273 per night (USD)VRBO
From $119 per night (USD)VRBO
2 Mi to Dtwn: Studio Suite in Sheboygan
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Pet Friendly w/ Fee | Walk to Diner & Brewery | Private Balcony Set sail for a getaway near the shore of Lake Michigan ...
From $119 per night (USD)VRBO
From $429 per night (USD)VRBO
Fully renovated, updated, and high-end finished 5 bedroom facing the marina!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
No expense spared in this fully renovated, updated, and high-end finished home facing the water and a block from the bea ...
From $429 per night (USD)VRBO
From $304 per night (USD)Expedia
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to King Park Beach Lookout Deluxe! Experience the perfect family getaway with panoramic views of Lake Michigan, ...
From $304 per night (USD)Expedia
From $287 per night (USD)VRBO
Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Riverwalk Retreat by Great lakes Getaways! Discover the ultimate retreat in this top-floor Riverfront condo with stunni ...
From $287 per night (USD)VRBO
From $274 per night (USD)Expedia
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Crystal Cove by Great Lakes Getaways! This lakeside condo boasts 2 bedrooms, 2 bathrooms, and a breathtaking view of La ...
From $274 per night (USD)Expedia
From $306 per night (USD)VRBO
Wonderful 3+ Bedroom Home Completely Renovated
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful home in Sheboygan WI. Entire home has been completely remodeled and updated. Three entire floors of space fo ...
From $306 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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From $231 per night (USD)VRBO
Centrally located house minutes away from the lake, golfing, & Road America.
- Bedrooms:
- 1
- 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 $231 per night (USD)VRBO
From $202 per night (USD)Expedia
LUX Uptown Escape - The Trester\n
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers ...
From $202 per night (USD)Expedia
From $192 per night (USD)VRBO
Riverfront Townhome with Breathtaking Water Views!
- Bedrooms:
- 1
- 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 $192 per night (USD)VRBO
From $307 per night (USD)Expedia
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 $307 per night (USD)Expedia
From $368 per night (USD)VRBO
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Perfect Paradise by Great Lakes Getaways! Unwind in this spacious 4-bedroom, 3-bath beachfront condo—perfect for famili ...
From $368 per night (USD)VRBO
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Perfect location for Ryder Cup!
- Bedrooms:
- 1
- 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 $216 per night (USD)VRBO
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 $216 per night (USD)VRBO
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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 $1483 per night (USD)VRBO
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n
- Bedrooms:
- 2
- 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 $1483 per night (USD)VRBO
From $246 per night (USD)VRBO
Pet-Friendly Sheboygan Home: 4 Mi to Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $246 per night (USD)VRBO
From $484 per night (USD)VRBO
Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 13
Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community 🌲 Just two blocks ...
From $484 per night (USD)VRBO
From $626 per night (USD)Expedia
Vacation Paradise: 4 Bedroom, Sleeps 14!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Enjoy life on the shores of Lake Michigan in this luxury, courtyard condo. This two-story, 4 bedroom/3 bathroom get-away ...
From $626 per night (USD)Expedia
From $2021 per night (USD)VRBO
Labor Day will be here before you know it. Celebrate with your favorite group!
- Bedrooms:
- 7
- 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 $2021 per night (USD)VRBO
From $1283 per night (USD)Expedia
Quiet and spacious home, close to downtown, the beach, and fantastic golfing.
- Bedrooms:
- 3
- 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 $1283 per night (USD)Expedia
From $175 per night (USD)VRBO
Seagull Beach Guest House, Unique Lake Michigan Cottage\non 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 $175 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:
- 2
- 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 $130 per night (USD)VRBO
Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This fantastic condo in Sheboygan offers two bedrooms with queen beds, perfect for a relaxing getaway. With amenities li ...
From $130 per night (USD)VRBO
From $1319 per night (USD)Expedia
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 20
🏡 Welcome to Baronwood Oasis – The Ultimate Family Escape - Sleeps 20 This is your moment to be the hero of your famil ...
From $1319 per night (USD)Expedia
From $619 per night (USD)VRBO
Luxury Lake Front Villa: Sleeps 12!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Experience the ultimate in luxury at this exquisite 4 bedroom lakefront vacation rental on Lake Michigan, just minutes f ...
From $619 per night (USD)VRBO
From $308 per night (USD)Expedia
Black River Retreat\nEclectic-Unique-Intriguing
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Wow. An amazing home in an amazing location. Minutes from downtown Sheboygan, beaches at Kohler Andre & Lakeview parks, ...
From $308 per night (USD)Expedia
From $434 per night (USD)VRBO
Boat in Sheboygan Harbor for Mercury Midwest Challenge!
- Bedrooms:
- 0
- Bathrooms:
- 2
- Sleeps:
- 5
40' Yacht on Lake Michigan, slipped at the Sheboygan Yacht Club. Come live aboard a 40ft by 13ft boat with all the mode ...
From $434 per night (USD)VRBO
From $165 per night (USD)Expedia
Beachside Condo Downtown 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 Waves of Happiness Condo hosted by S ...
From $165 per night (USD)Expedia
From $454 per night (USD)VRBO
Charming 4-bedroom house with WiFi and AC in lovely Sheboygan
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Unwind in this fabulous 1970's home with modern upgrades. This spacious 3700 SF retreat features 4 bedrooms (3 queen, ...
From $454 per night (USD)VRBO
From $197 per night (USD)Expedia
Sunset Vista 2br in Sheboygan
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
This cozy vacation rental is a perfect place to relax and enjoy a getaway! From its warm and inviting fireplace, with co ...
From $197 per night (USD)Expedia
From $695 per night (USD)VRBO
Modern Lakeside House with Treehouse
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to Curtiss Castle! Ideal for large families, remote workers, lake lovers, and golf enthusiasts! This peaceful, w ...
From $695 per night (USD)VRBO
From $551 per night (USD)Expedia
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)Expedia
From $176 per night (USD)VRBO
Sheboygan Sunrise Beach Stay
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
*** STEPS AWAY FROM LAKE MICHIGAN*** Experience the vibrant energy from our stylish apartment with great views. Enjoy e ...
From $176 per night (USD)VRBO
From $371 per night (USD)Expedia
NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Your much-needed retreat begins at this large 3-bedroom house 300-feet from Lake Michigan. This wonderful property featu ...
From $371 per night (USD)Expedia
From $375 per night (USD)VRBO
State Park w/ Orchard Style Yard & Pavilion
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our Orchard House Retreat, hosted by Sheboygan Vacation Rentals. Our home is situated directly across from t ...
From $375 per night (USD)VRBO
From $300 per night (USD)Expedia
Lighthouse Lookout - 3BR / Steps to Lake Michigan & Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Lighthouse Lookout by Great Lakes Getaways! Discover the ultimate retreat at Sheboygan's Riverfront condo with stunning ...
From $300 per night (USD)Expedia
From $1286 per night (USD)VRBO
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Welcome to Fairway Getaway! This stunning property combines luxury, comfort, and convenience, making it the perfect choi ...
From $1286 per night (USD)VRBO
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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 $233 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 $233 per night (USD)VRBO
From $333 per night (USD)VRBO
Peaceful Retreat, Near Road America! Mid Century Modern Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Peaceful and private getaway in the woods, yet close to everything! Shops, restaurants, bars, parks, golf, fishing, sail ...
From $333 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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From $284 per night (USD)Expedia
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The Cottage by Great Lakes Getaways! Escape to this newly renovated beachfront condo nestled along the serene shores of ...
From $284 per night (USD)Expedia