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

Sheboygan Rentals

From $243 per night (USD)
VRBO
3 Bedroom Beach House
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Three-bedroom house with full kitchen, dining room with spacious living room to watch movies, relax, play board games an ...
From $243 per night (USD)
VRBO
From $227 per night (USD)
Expedia
REMODELED HOME ON LAKE MICHIGAN
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
3 Bedrooms and 1.5 Baths in this two-story brick home. Located about one mile south of downtown Sheboygan on a bluff ove ...
From $227 per night (USD)
Expedia
From $435 per night (USD)
VRBO
5 Bedroom Modern House
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
5 bedroom modern home. Full kitchen includes dishwasher, microwave, stove, fridge, keurig, everyday utensils and pans. P ...
From $435 per night (USD)
VRBO
From $261 per night (USD)
VRBO
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
100
Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bathroom Sheboygan vac ...
From $261 per night (USD)
VRBO
$Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach$
From $230 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 $230 per night (USD)
VRBO
From $163 per night (USD)
VRBO
The River Bed - Condo sleeps 4 on west side
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
5 minutes from Kohler & minutes from world class champion golf courses! Brand new & clean! Just completed condo with 2 ...
From $163 per night (USD)
VRBO
From $419 per night (USD)
VRBO
Family Home, 1 Block to Lake Michigan Beach!
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
- Game Room - Central Location - Recently Remodeled From Lake Michigan to downtown, there's something for everyone at t ...
From $419 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
$Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA$
From $563 per night (USD)
VRBO
Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA
Bedrooms:
2
Bathrooms:
4
Sleeps:
12
Amazing location just 3 blocks of Lake Michigan. a short walk to the public south beach, 2 min driving to the beach. 4 ...
From $563 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 $181 per night (USD)
VRBO
Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, gol ...
From $181 per night (USD)
VRBO
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Expedia
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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Expedia
From $222 per night (USD)
VRBO
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Modern/updated 2 bedroom 2 bath townhouse on a quite Cul-De-Sac in Sheboygan, WI. Every part of this house has been remo ...
From $222 per night (USD)
VRBO
From $1986 per night (USD)
Expedia
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.
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 $1986 per night (USD)
Expedia
From $1424 per night (USD)
VRBO
Shoreline Sanctuary - 4 Bedroom Beachfront Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to your perfect getaway at Shoreline Sanctuary! This beautifully updated and meticulously maintained condo is a ...
From $1424 per night (USD)
VRBO
From $676 per night (USD)
Expedia
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Our beautiful lakefront home is perfect for a relaxing retreat! Minutes to downtown Sheboygan, downtown Kohler with 5 ...
From $676 per night (USD)
Expedia
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VRBO
Ryder Cup - Premier Location!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This newly remodeled and professionally cleaned home is 8 minutes from Whistling Straits and within walking distance to ...
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VRBO
From $334 per night (USD)
VRBO
Dtwn Sheboygan Apt Above Local Bar!
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your nex ...
From $334 per night (USD)
VRBO
From $347 per night (USD)
VRBO
Art Collector’s Dream • Remodeled Masterpiece with Gallery Vibes
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parki ...
From $347 per night (USD)
VRBO
From $402 per night (USD)
Expedia
Beach and Golf House
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
This home is in the perfect location to explore everything Sheboygan County has to offer. It is located in the historic ...
From $402 per night (USD)
Expedia
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 $141 per night (USD)
VRBO
2BR, 1.5BA, Pet-friendly, Lower duplex w/finished basement + large backyard!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
This 2 bedroom, 2 bath lower duplex is the perfect spot to stay! It's just 3 short blocks to all of the restaurants of S ...
From $141 per night (USD)
VRBO
From $315 per night (USD)
VRBO
Classic brick charmer close to lake, river, and downtown!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Our classic 3 bedroom, 1 bathroom brick home located in the Historic Ellis District is central to the best experiences i ...
From $315 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 $232 per night (USD)
VRBO
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This an Upstairs Duplex with 2 bedrooms and 1 bath. Features a kitchen stocked with pots, pans, utensils, and kitchen ga ...
From $232 per night (USD)
VRBO
From $187 per night (USD)
Expedia
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road Amer ...
From $187 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
From $308 per night (USD)
Expedia
Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
Bedrooms:
2
Bathrooms:
3
Sleeps:
9
Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with ...
From $308 per night (USD)
Expedia
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VRBO
Apt w/ Shared Gas Grill, 2 Blocks to Dtwn!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Escape to Lake Michigan when you choose this centrally located Sheboygan vacation rental! Bring your fishing rods to spe ...
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VRBO
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Expedia
Ryder Cup 2021 - Home near Lake Michigan, 6 miles from Whistling Straits
Bedrooms:
2
Bathrooms:
5
Sleeps:
10
This mid-century modern home is situated in a quiet north Sheboygan Neighborhood, a 2 min walk to the Lake Michigan shor ...
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Expedia
From $150 per night (USD)
VRBO
BEST LOCATION IN SHEBOYGAN! Steps to beach & marina, walk to historic downtown!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
My husband and I love to stay in a reasonably priced condo or flat when we travel. We like to feel like we are at a home ...
From $150 per night (USD)
VRBO
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Expedia
10 min drive to Whistling Straits Golf course
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
4 bedroom House with 2.5 baths and finished basement. Lots of extra room to spread out or add air mattresses to accommod ...
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Expedia
From $274 per night (USD)
VRBO
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping ...
From $274 per night (USD)
VRBO
From $231 per night (USD)
VRBO
Scenic Lake Views in Sheboygan
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Watch the sun/moon come up over Lake Michigan across from the Sheboygan Marina and scenic lighthouse in this beautifully ...
From $231 per night (USD)
VRBO
From $809 per night (USD)
VRBO
'Beautiful Day Getaway' - Lake Michigan Views
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Set your sights on the coastal community of Sheboygan, where you can find 2 miles of sandy beaches, epic sailing, and a ...
From $809 per night (USD)
VRBO
From $349 per night (USD)
VRBO
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
4
Sleeps:
10
Whether you’re on the hunt for some good cheese, a delicious fried brat or just a simple lake retreat, this vacation ren ...
From $349 per night (USD)
VRBO
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VRBO
Fun family home near Ryder Cup
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Minutes from Ryder Cup, steps from Lake Michigan. 4 bedroom home with open concept family room, kitchen, and formal dini ...
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VRBO
From $827 per night (USD)
Expedia
Central located. Seconds from the highway to get to kohler, and Elkhart lake
Bedrooms:
2
Bathrooms:
4
Sleeps:
14
Everything you need on one level. complete modern Open concept living room, kitchen and dinning area. Hosts two large k ...
From $827 per night (USD)
Expedia
From $202 per night (USD)
VRBO
2BR Duplex Lower Overlooking Kiwanis Park
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
This 2BR lower unit of a duplex is located in a quiet neighborhood, yet it is within walking distance of 2 coffee shops, ...
From $202 per night (USD)
VRBO
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Expedia
Northside Charmer!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Charming Northside Sheboygan home just 5 miles from Whistling Straits, a ten minute walk to Lake Michigan and 15 minute ...
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Expedia
From $198 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 $198 per night (USD)
VRBO
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Expedia
Beautiful Historic Home Near Lake Michigan
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
Beautiful historic home near Lake Michigan, only 6 blocks away. This house offers 4 bedrooms, 2 full bathrooms dinning ...
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Expedia
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VRBO
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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VRBO
From $404 per night (USD)
Expedia
BEACHVIEW GETAWAY
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Amazing location just off of Lake Michigan. A quick walk to the public beach across the street or downtown as well. Prev ...
From $404 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Riverfront Sheboygan Townhome w/ Grill!
Bedrooms:
1
Bathrooms:
2
Sleeps:
8
Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. Th ...
From $193 per night (USD)
VRBO
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Expedia
16 MIN FROM RYDERCUP Wooded Retreat
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
3000 sq ft ranch 16 minutes from the Ryder Cup, this lovely 4 bed/2 bath is nestled in a beautiful wooded neighborhood a ...
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Expedia
From $191 per night (USD)
VRBO
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Whether you're here to visit friends or family, this lower-level 2-bed, 1-bath Sheboygan vacation rental apartment has a ...
From $191 per night (USD)
VRBO
From $277 per night (USD)
Expedia
Malibu of the Midwest Condo steps from the Lake
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
7th Heaven Condo is in the popular South Pier district. Cute condo is on the 2nd floor with elevator access. Across the ...
From $277 per night (USD)
Expedia
From $199 per night (USD)
VRBO
Logan Ave Holiday House - Upper
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Unique attractions and endless days by Lake Michigan await at this ideally located vacation rental! Hosting 2 bedrooms, ...
From $199 per night (USD)
VRBO
From $346 per night (USD)
Expedia
Beach front luxury spacious villa !
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beach front luxury spacious condo! Beautiful remodeled four bedroom villa/condo overlooking Lake Michigan, well equippe ...
From $346 per night (USD)
Expedia
From $225 per night (USD)
VRBO
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
More than just an inviting home away from home. It’s a friendly gesture, usually followed by a smile, and exchanged betw ...
From $225 per night (USD)
VRBO
From $262 per night (USD)
Expedia
4 Bedroom Home on the River with Private River access
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Take in the coastal vibes as you enjoy your stay at this Riverfront home. With private access to the river, kayaks to us ...
From $262 per night (USD)
Expedia
From $364 per night (USD)
VRBO
LUXE Manor with Modern, Elegant Vibes
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Modern chic blends with classic sophistication in this late 1800s Manor. Enjoy the expansive 4,500 square feet of elegan ...
From $364 per night (USD)
VRBO
From $219 per night (USD)
VRBO
Family-Friendly House: Walk to Lake Michigan!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Spend fun-filled days with your surfboard when you choose this conveniently located Sheboygan vacation rental! Just unde ...
From $219 per night (USD)
VRBO
From $494 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 $494 per night (USD)
VRBO
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Expedia
Top Floor Condo With Lake Michigan Views Throughout!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Relax in this luxurious new construction condo! Enjoy top floor Lake Michigan Views from every room! Balcony with lots o ...
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Expedia
From $110 per night (USD)
VRBO
COMFY, COZY, and CONVENIENT!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you are visiting for golf, fishing, a Green Bay Packer game, Road America, or simply a vacation, this convenient ...
From $110 per night (USD)
VRBO
From $355 per night (USD)
Expedia
*NEW* Sleeps 8 & Spacious!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $355 per night (USD)
Expedia
From $318 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 $318 per night (USD)
VRBO
From $324 per night (USD)
Expedia
*NEW* Beautiful & Convenient!
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $324 per night (USD)
Expedia
From $552 per night (USD)
VRBO
A Glorious Getaway Sheboygan - LUX Lake Condo
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Welcome to a Glorious Getaway! Steps to Lake Michigan come and enjoy this luxury 4 bed 3 bath condo. Located i ...
From $552 per night (USD)
VRBO
From $220 per night (USD)
Expedia
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Welcome to the Relax ‘n Retreat! Retreat: noun - a quiet or secluded place in which one can rest and relax Unwind at o ...
From $220 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Beach House on the shores of Lake Michigan Near downtown Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Amazing location on the shores of Lake Michigan. One of only a few homes in the city of Sheboygan that are right on the ...
From $495 per night (USD)
VRBO
From $313 per night (USD)
Expedia
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 $313 per night (USD)
Expedia
From $290 per night (USD)
VRBO
Beautiful 3BR Home Near Lake MI
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
🏡 Overview Relax and recharge in this charming 3-bedroom, 1.5-bath home just one block from Lake Michigan. Nestled in a ...
From $290 per night (USD)
VRBO
From $284 per night (USD)
Expedia
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Come stay at a beautiful home close to Lake Michigan and downtown Sheboygan! Located in a quiet neighborhood, and two b ...
From $284 per night (USD)
Expedia
From $247 per night (USD)
VRBO
Serene Home One Block From Lake Michigan
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our spacious, two-story 3-bedroom, 2-bathroom home just one block from Lake Michigan and beautiful Deland Par ...
From $247 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
From $310 per night (USD)
VRBO
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Plan for plenty of outdoor fun on your next Lake Michigan getaway when you stay at this Sheboygan vacation rental! With ...
From $310 per night (USD)
VRBO
From $294 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 $294 per night (USD)
VRBO
From $119 per night (USD)
VRBO
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Place is all for you! No share place. Forget your worries in this spacious and serene Guest House ( sleeps 4 people) q ...
From $119 per night (USD)
VRBO
From $159 per night (USD)
Expedia
Sleeps 7{SPACIOUS}Pets Welcome!
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally ...
From $159 per night (USD)
Expedia
$LUX Uptown Escape - The Trester\n$
From $179 per night (USD)
VRBO
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 $179 per night (USD)
VRBO
From $205 per night (USD)
Expedia
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 $205 per night (USD)
Expedia
From $126 per night (USD)
VRBO
Cute Quiet Neighborhood Hideway
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Step back in time and relax in this 1930’s bungalow. Situated on the south side of the City of Sheboygan, able to feel t ...
From $126 per night (USD)
VRBO
From $742 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 $742 per night (USD)
VRBO
From $222 per night (USD)
VRBO
The Cottage - Newly Renovated Beachfront Condo on Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
The Cottage by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $222 per night (USD)
VRBO
From $426 per night (USD)
Expedia
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Enjoy your Sheboygan getaway in this spacious 4-bedroom, 2-bath home just a 5-minute walk to the lake. Sleeps 11 and pac ...
From $426 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Lovely Lake Lookout - Cozy 2BR Condo Steps from Lake Michigan
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Lovely Lake Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $145 per night (USD)
VRBO
From $241 per night (USD)
Expedia
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Nestled in the heart of Sheboygan, our location is a true gem! We are just steps away from the shores of Lake Michigan a ...
From $241 per night (USD)
Expedia
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
From $1230 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 $1230 per night (USD)
VRBO
From $234 per night (USD)
VRBO
Modern South Pier Condo on Sheboygan River!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Stay in luxury at this 2-bedroom, 2-bathroom vacation rental in Sheboygan, WI. Enjoy the convenience of a fully equipped ...
From $234 per night (USD)
VRBO
From $177 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 $177 per night (USD)
VRBO
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Expedia
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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Expedia
From $1167 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 $1167 per night (USD)
VRBO
From $136 per night (USD)
VRBO
Cozy and private 3 bedroom unit located a few blocks from downtown Sheboygan.
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Located just a couple blocks from downtown Sheboygan! Visit the shops and unique restaurants just a short walk away, or ...
From $136 per night (USD)
VRBO
From $134 per night (USD)
VRBO
Urban Lake Condo in Sheboygan's Historic Ellis District
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Your family will be within walking distance of almost everything when you stay at this centrally-located harborside gem ...
From $134 per night (USD)
VRBO
From $148 per night (USD)
VRBO
Dog-Friendly Sheboygan Home - 1 Mi to Town!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience the best of Sheboygan with your loved one from this 1-bed, 1-bath vacation rental! This newly renovated home ...
From $148 per night (USD)
VRBO
From $255 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! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2 ...
From $255 per night (USD)
VRBO
From $74 per night (USD)
VRBO
Lakeside Condo - 2BR, Lake Michigan Views & Massage Chair
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Crystal Cove by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026. ...
From $74 per night (USD)
VRBO
From $262 per night (USD)
VRBO
Lighthouse Lookout - 3BR / Steps to Lake Michigan & Views
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lighthouse Lookout by Great Lakes Getaways! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $262 per night (USD)
VRBO
$\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy$
From $766 per night (USD)
Expedia
\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Grand colonial meets coastal luxe in this 2800 square ft, 4 bedroom home along the magnificent Lake Michigan coast. Stun ...
From $766 per night (USD)
Expedia
From $552 per night (USD)
VRBO
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Luxury Modern Farmhouse 4B-2Ba Lake & Beach House! Is it time for a Cool Change? Relax and rejuvenate at Sheboygan's n ...
From $552 per night (USD)
VRBO
From $158 per night (USD)
Expedia
Downtown, Uniquely Designed, Near the Beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Welcome to the Uptown Coach House, hosted by Sheboygan Vacation Rentals. Our newly built coach house is nestled in the ...
From $158 per night (USD)
Expedia
From $355 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 $355 per night (USD)
VRBO
From $186 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! Take advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, ...
From $186 per night (USD)
VRBO
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 $421 per night (USD)
Expedia
Charming 3-bedroom 3 Bathroom house in Sheboygan with AC, WiFi, & Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy a peaceful stay at this cozy 3-bedroom, 3 living room, and 3 bathroom home in Sheboygan, WI. This charming propert ...
From $421 per night (USD)
Expedia
From $561 per night (USD)
VRBO
Executive Beachfront Villa: Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Just steps from Lake Michigan, this updated 2BR/2BA condo features modern décor, new flooring, and refreshed showers for ...
From $561 per night (USD)
VRBO
From $263 per night (USD)
Expedia
Lakefront Condo- Step-free & accessible! Sleeps 8!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Enjoy the beauty of Lake Michigan just steps from your door in this 2BR/2BA beachfront condo. Located near the boardwalk ...
From $263 per night (USD)
Expedia

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Results: 137 Rentals