Sheboygan Area, Wisconsin Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Sheboygan Area, Wisconsin on RentalSaver.com!

Sheboygan Area Rentals

$Spacious Blue Harbor 2 bedr courtyard view condo w\/ Breaker Bay Waterpark access$
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VRBO
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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VRBO
$Fairway Getaway-by Whistling Straits, Golf sim\/Theater Room, ZenDen &Poker Room!$
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
$Studio 920 #5 - Cool Studio w\/ AC Monthly Rentals!$
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VRBO
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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VRBO
From $351 per night (USD)
Expedia
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Welcome to The Hemisphere House, a unique dome retreat in a charming Wisconsin neighborhood. This architectural gem offe ...
From $351 per night (USD)
Expedia
$Across from Kohler-Andrae w\/ Orchard Style Yard & Pavilion$
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 $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
$Farm Fresh Eggs, Amazing Outdoor Space w\/ Fire Pit$
From $439 per night (USD)
VRBO
Farm Fresh Eggs, Amazing Outdoor Space w\/ Fire Pit
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
ESCAPE THE ORDINARY AT THIS ONE-OF-A-KIND, HISTORIC PROPERTY. You feel right at home the moment you walk through the do ...
From $439 per night (USD)
VRBO
$Premier View and Patio Overlooking Elkhart Lake! Two minute walk to bars\/dining!$
From $666 per night (USD)
Expedia
Premier View and Patio Overlooking Elkhart Lake! Two minute walk to bars\/dining!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy listening to bands from the private large patio while overlooking Elkhart Lake and the pool. Updated nice furnish ...
From $666 per night (USD)
Expedia
$Lakefront Penthouse, Private Beach, Outdoor\/Indoor Pools, Walk to Town$
From $440 per night (USD)
VRBO
Lakefront Penthouse, Private Beach, Outdoor\/Indoor Pools, Walk to Town
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Fall in love with Elkhart Lake at this luxury Elkhart Lake Penthouse! Enjoy breathtaking views of Elkhart Lake from ever ...
From $440 per night (USD)
VRBO
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 $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 $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
$NEW! Crystal Cove - Lux Lakefront Condo w\/ Massage Chair. Walk to Lake Michigan!$
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 $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
$LUX Uptown Escape - The Trester\n$
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 $148 per night (USD)
VRBO
Cozy Cape Cod Home
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy cape cod home behind the Plymouth racetrack, loud during race season. Close to Road America (8 min; 5.8 miles), nea ...
From $148 per night (USD)
VRBO
$White House on the Mill Pond - kayak\/walk downtown$
From $368 per night (USD)
VRBO
White House on the Mill Pond - kayak\/walk downtown
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
About this space A mix of vintage charm & contemporary/clean with leather couches, hardwood & tile floors. This is a 2 b ...
From $368 per night (USD)
VRBO
From $818 per night (USD)
VRBO
The Woods Estate - walk to Road America & near Kohler Golf ~ Modern Luxury
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Experience the beauty & comfort if this luxury contemporary home nestled in the woods on 5 acres walking distance to Ro ...
From $818 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 $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 $293 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 $293 per night (USD)
Expedia
$Simply Stunning Family Style W\/ 6 Pools$
From $563 per night (USD)
VRBO
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)
VRBO
From $824 per night (USD)
VRBO
Lakeside luxury. Walk to Road America + Hot Tub
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Beautiful lake home located directly on Little Elkhart Lake. Home features 3 bedrooms, 2 full bathrooms & 2 spacious liv ...
From $824 per night (USD)
VRBO
From $1504 per night (USD)
VRBO
Beachfront property with panoramic view of Lake Michigan!
Bedrooms:
6
Bathrooms:
8
Sleeps:
20
Create memories at this beautiful Lake Michigan beachfront home. At the end of a private road, this year-round lake hous ...
From $1504 per night (USD)
VRBO
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Expedia
Track View Townhome Next to Road America
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
• 4 car heated garage • Trailer parking • Gas grill • Keyless entry • Washer+dryer–soap/dryer sheets provided • 1 king b ...
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Expedia
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VRBO
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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VRBO
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Expedia
Dance Hall, Events Welcome, Sleeps 16+, Pets OK
Bedrooms:
0
Bathrooms:
0
Sleeps:
0
Dive into the history of this unique and memorable place. We allow guests to host small weddings and events during their ...
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Expedia
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VRBO
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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VRBO
$Large lakefront Cabin w\/ year-round activities & enough beds for everyone!$
From $672 per night (USD)
VRBO
Large lakefront Cabin w\/ year-round activities & enough beds for everyone!
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Relax with the whole family at this peaceful lakefront cabin! Wake up to stunning views and days filled with kayaking, h ...
From $672 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
From $490 per night (USD)
VRBO
Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
**2022 calendar is open. Please note that our peak season rentals are a week minimum and run Monday-Monday** To reach K ...
From $490 per night (USD)
VRBO
From $644 per night (USD)
VRBO
Stunning custom built country home with the ultimate game room!
Bedrooms:
4
Bathrooms:
6
Sleeps:
14
The search is over, you have found the PERFECT retreat at Oaks Haven! Experience the tranquility of nature surrounded by ...
From $644 per night (USD)
VRBO
From $476 per night (USD)
VRBO
Heart of the Action, Village Square Upper Condo Sleeps 8
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Upper 4BR/2BA condo unit on the Village Park! Central location on Village Square across from historic train depot and re ...
From $476 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 $198 per night (USD)
Expedia
cute and cozy-minutes from beaches,parks,trails,entertainment!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Cute comfortable open concept 2 bedroom apartment adjacent/ above The Dundee's Roadhouse super fun full service food and ...
From $198 per night (USD)
Expedia
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VRBO
25 min. to Kohler Resort, Golf, Spa, Dining
Bedrooms:
6
Bathrooms:
6
Sleeps:
14
This 5,500 square feet home sits directly on Lake Michigan. 6 Bedrooms and 4 full baths plus 2 1/2 baths. Located in Ced ...
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VRBO
From $333 per night (USD)
Expedia
'McJugger’s Loft:' Walk to Lake, Park, Restaurants
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Experience small-town Wisconsin from this 3-bed, 2-bath vacation rental! 'McJugger's Loft' is ideal for a family trip, c ...
From $333 per night (USD)
Expedia
From $503 per night (USD)
VRBO
The Lakehouse on Long Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Our family always dreamt of owning a Lakehouse. When we had the opportunity to finally make that dream come true, we cra ...
From $503 per night (USD)
VRBO
From $455 per night (USD)
Expedia
Beautiful new year round Lake home on Long Lake in Kettle Moraine State forest
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Long Lake is a 432 Acre full recreational lake, known for water clarity, fishing, swimming, water skiing, boating , ice ...
From $455 per night (USD)
Expedia
$Lillibridge Lake Home on Tittle Lake\/Long Lake All Season Fun$
From $181 per night (USD)
VRBO
Lillibridge Lake Home on Tittle Lake\/Long Lake All Season Fun
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
The Lillibridge Lake House is just steps from the water on quaint Tittle Lake, nestled in the Kettle Moraine State Fores ...
From $181 per night (USD)
VRBO
From $422 per night (USD)
Expedia
Clara's Cottage, On Lake Michigan
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
The cottage is located approximately 45 minutes north of Milwaukee and ,10 minutes south of historic Sheboygan/Kohler ...
From $422 per night (USD)
Expedia
$Colorful Cottage w\/ Hot Tub - Steps to Long Lake!$
From $377 per night (USD)
VRBO
Colorful Cottage w\/ Hot Tub - Steps to Long Lake!
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Prepare to experience lake life at this vacation rental in Campbellsport. Sitting across the street from Long Lake, this ...
From $377 per night (USD)
VRBO
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Expedia
RYDER CUP RENTAL : rustic lake front log cabin - 45min to Ryder Cup
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Log Cabin with loads of rustic charm situated on Forest Lake, Campbellsport, WI., a spring feed lake surrounded by the n ...
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Expedia
$Lakefront Campbellsport Retreat w\/ Dock & Yard!$
From $370 per night (USD)
VRBO
Lakefront Campbellsport Retreat w\/ Dock & Yard!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Discover your own slice of Wisconsin heaven at this 4-bedroom, 2.5-bathroom Campbellsport vacation rental! You'll be in ...
From $370 per night (USD)
VRBO
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
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 $439 per night (USD)
VRBO
On the Shores of Lake Michigan with Breathtaking Views & A Beach Out Your Door!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Private and Charming Beach Bungalow located on a secluded road! Who said this is a lake? This feels more like an ocean ...
From $439 per night (USD)
VRBO
From $469 per night (USD)
VRBO
Rustic 3BR cottage on beach, 40 min from downtown Milwaukee.
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
This 3BR rustic cottage is quietly tucked away and just steps away from the shoreline of Lake Michigan. Large deck for ...
From $469 per night (USD)
VRBO
From $686 per night (USD)
VRBO
The Long Lake Chalet
Bedrooms:
1
Bathrooms:
3
Sleeps:
10
This recently remodeled and tastefully furnished, PET FRIENDLY, cabin boasts a unique charm. Nestled along the shores of ...
From $686 per night (USD)
VRBO
From $536 per night (USD)
Expedia
Charming Retreat with Panoramic Views near Oostburg, Sheboygan, and Kohler
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Discover the epitome of lakeside living in this charming house nestled along Lake Michigan's serene shores, near Oostbur ...
From $536 per night (USD)
Expedia
$Welcome to the \Lake Cottage\ where lake Michigan waves are calling$
From $321 per night (USD)
VRBO
Welcome to the \"Lake Cottage\" where lake Michigan waves are calling
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Make memories of a lifetime at the “Lake Cottage” On a private gravel road right on the Lake 1.5 hours north of Chicago, ...
From $321 per night (USD)
VRBO
From $166 per night (USD)
Expedia
GGG Log Cabin Apartment on the Ice Age Trail
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
With 10-11’ ceilings and 1000 sf, this sunny apartment is the second floor of an 1860’s log cabin. Completely updated wi ...
From $166 per night (USD)
Expedia
From $984 per night (USD)
VRBO
Serene Lakeview Retreat on Lake Michigan - Minutes to Whistling Straights
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Relax in this beautiful secluded home with breathtaking views of Lake Michigan. This spacious 4 bedroom home is showered ...
From $984 per night (USD)
VRBO
$NEW! Lakeview Cottage on 3.5 acres w\/hot tub and fire pit$
From $341 per night (USD)
Expedia
NEW! Lakeview Cottage on 3.5 acres w\/hot tub and fire pit
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
NEW Modern cottage on Lake Michigan’s coast nestled on spacious 3.5 acres. Outdoors you can relax and unwind in the seve ...
From $341 per night (USD)
Expedia
From $154 per night (USD)
VRBO
LAKE HOUSE Realx'n in or on the water this is your place for memories to be made
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Kettle Moraine Long Lake Vacation Get Away. Comfort begins as you enter the door to your lake frontage studio style vaca ...
From $154 per night (USD)
VRBO
From $289 per night (USD)
Expedia
Cascade Lakefront Home: Boat Dock, Fire Pit!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Prepare for your ultimate lakeside retreat at this newly renovated Cascade lakefront property. Sitting right on Long Lak ...
From $289 per night (USD)
Expedia
From $283 per night (USD)
VRBO
Cottage in Campbellsport
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
The Retreat on Long Lake is the transformation of a cottage into a newly renovated and stylish experience. The house i ...
From $283 per night (USD)
VRBO
From $201 per night (USD)
VRBO
Sunset Views by Long Lake
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This A-frame cottage boasts 3 inviting bedrooms. The bedrooms will ensure a comfortable stay for all guests. The cozy a ...
From $201 per night (USD)
VRBO
From $353 per night (USD)
VRBO
From Schwarz Supper Club to Road America, Schwarz Guest House is in Between.
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The Schwarz family has been taking care of friends and customers for over 55 years. Dinner, drinks, and a good time is ...
From $353 per night (USD)
VRBO
$NEW! Hidden Haven on 3.5 Acres w\/ Hot Tub and Fire Pit$
From $322 per night (USD)
VRBO
NEW! Hidden Haven on 3.5 Acres w\/ Hot Tub and Fire Pit
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to Hidden Haven by Great Lakes Getaways! Discover our new modern cottage on Lake Michigan’s coast, nestled on a ...
From $322 per night (USD)
VRBO
From $836 per night (USD)
VRBO
Just listed-newly renovated home on Lake Michigan - heated pool- Ozaukee County
Bedrooms:
4
Bathrooms:
4
Sleeps:
11
Welcome to Wisco Lakehouse! Our lakefront home is perfect year-round for a fun family vacation, couple’s getaway, golf t ...
From $836 per night (USD)
VRBO

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Sheboygan Area Rentals

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Results: 361 Rentals