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

Sheboygan Rentals

From $724 per night (USD)
VRBO
Just 75 steps from the sand and shore of Lake Michigan!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
This listing is for the villa only. Blue Harbor water park passes are not included and currently unavailable to purchase ...
From $724 per night (USD)
VRBO
From $322 per night (USD)
Expedia
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 $322 per night (USD)
Expedia
From $368 per night (USD)
VRBO
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 $368 per night (USD)
VRBO
From $482 per night (USD)
Expedia
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 $482 per night (USD)
Expedia
From $255 per night (USD)
VRBO
Updated Sheboygan Home w/ Porch < 1 Mi to Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Discover contemporary comfort right beside Lake Michigan’s coast with a trip to this 3-bedroom, 2-bathroom Sheboygan vac ...
From $255 per night (USD)
VRBO
$Seagull Beach Guest House, Unique Lake Michigan Cottage\non private beach$
From $187 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 $187 per night (USD)
VRBO
From $172 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 $172 per night (USD)
VRBO
From $313 per night (USD)
Expedia
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 $313 per night (USD)
Expedia
From $1283 per night (USD)
VRBO
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)
VRBO
$Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA$
From $544 per night (USD)
Expedia
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 $544 per night (USD)
Expedia
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 $227 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 $227 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $279 per night (USD)
Expedia
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 $279 per night (USD)
Expedia
From $2096 per night (USD)
VRBO
Give Dad a memorable Father’s Day Weekend in Wisconsin!
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 $2096 per night (USD)
VRBO
From $1424 per night (USD)
Expedia
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)
Expedia
From $693 per night (USD)
VRBO
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 $693 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $197 per night (USD)
VRBO
Downtown Sheboygan Apartment w/ Private Deck!
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 $197 per night (USD)
VRBO
From $394 per night (USD)
Expedia
Original Art |1904 Classic | Near Beach & Downtown
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 $394 per night (USD)
Expedia
From $402 per night (USD)
VRBO
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)
VRBO
From $561 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 $561 per night (USD)
Expedia
From $329 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 $329 per night (USD)
VRBO
Click For Pricing
Expedia
Geele Ave Rental for Ryder Cup
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
3 bedroom 2.5 bath home located near Lake Michigan and Downtown restaurants and shopping. Ready for the Women’s Golf Tou ...
Click For Pricing
Expedia
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 $245 per night (USD)
VRBO
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 $245 per night (USD)
VRBO
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 $329 per night (USD)
VRBO
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 $329 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
This location is13 minutes from 2020 Ryder cup at Whistling straights. It's 2 blocks from the beach on lake Michigan. We are only 3 blocks from numerous restaurants and local bars.
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
This house is warm and inviting. The fenced in backyard has a comfortable and covered patio area, with 2 propane fire p ...
Click For Pricing
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
From $319 per night (USD)
Expedia
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 $319 per night (USD)
Expedia
From $239 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 $239 per night (USD)
VRBO
From $811 per night (USD)
Expedia
'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 $811 per night (USD)
Expedia
From $350 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 $350 per night (USD)
VRBO
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia
From $811 per night (USD)
VRBO
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 $811 per night (USD)
VRBO
From $149 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 $149 per night (USD)
VRBO
Click For Pricing
VRBO
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 ...
Click For Pricing
VRBO
Click For Pricing
Expedia
5mi from the Ryder Cup @ Whistling Straits, natural beauty and serenity awaits!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Sleeping 8, this ranch home located just 6 miles as the crow flies from Whistling Straits golf course, offers a relaxing ...
Click For Pricing
Expedia
From $233 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 $233 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $437 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 $437 per night (USD)
Expedia
From $203 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 $203 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
From $277 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 $277 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 $262 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 $262 per night (USD)
VRBO
From $690 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 $690 per night (USD)
Expedia
From $224 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 $224 per night (USD)
VRBO
From $318 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 $318 per night (USD)
Expedia
From $438 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 $438 per night (USD)
VRBO
From $217 per night (USD)
Expedia
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 $217 per night (USD)
Expedia
From $996 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 $996 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
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 ...
Click For Pricing
VRBO
From $130 per night (USD)
VRBO
COMFY, COZY, and CONVENIENT!!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Whether you are here for golf, fishing, a Green Bay Packer game, Road America, or simply a vacation, this convenient She ...
From $130 per night (USD)
VRBO
From $404 per night (USD)
VRBO
*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 $404 per night (USD)
VRBO
From $332 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 $332 per night (USD)
Expedia
From $310 per night (USD)
VRBO
*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 $310 per night (USD)
VRBO
From $1198 per night (USD)
Expedia
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 $1198 per night (USD)
Expedia
From $277 per night (USD)
VRBO
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 $277 per night (USD)
VRBO
From $470 per night (USD)
Expedia
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 $470 per night (USD)
Expedia
From $421 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 $421 per night (USD)
VRBO
From $331 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 $331 per night (USD)
VRBO
From $277 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 $277 per night (USD)
VRBO
Click For Pricing
Expedia
Remodeled Cape Cod within steps of Lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
8
Our charming Cape Cod home is waiting for you! With 3 bedrooms, and 1.5 baths, we’re sure our home will meet the needs o ...
Click For Pricing
Expedia
From $247 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 $247 per night (USD)
VRBO
From $262 per night (USD)
Expedia
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 $262 per night (USD)
Expedia
From $353 per night (USD)
VRBO
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 $353 per night (USD)
VRBO
$LUX Uptown Escape - The Trester\n$
From $389 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 $389 per night (USD)
Expedia
From $247 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 $247 per night (USD)
VRBO
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 $527 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 $527 per night (USD)
VRBO
From $328 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 $328 per night (USD)
Expedia
From $454 per night (USD)
VRBO
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 $454 per night (USD)
VRBO
From $155 per night (USD)
VRBO
3 Bedroom lower unit -Brand New Remodel
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Complete Remodel just finished on this 3 BR 1 BA lower unit. New bathroom, kitchen, flooring, etc. in a central location ...
From $155 per night (USD)
VRBO
From $314 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! Unwind at this cozy 2BR/2BA condo just moments from Lake Michigan. Enjoy e ...
From $314 per night (USD)
VRBO
From $538 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 $538 per night (USD)
Expedia
$Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan\n$
From $1619 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 $1619 per night (USD)
VRBO
From $243 per night (USD)
Expedia
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 $243 per night (USD)
Expedia
From $343 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 $343 per night (USD)
VRBO
Click For Pricing
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 ...
Click For Pricing
Expedia
Click For Pricing
VRBO
Lakeview Loft - Just opened up for July!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Looking for extended stays? We offer monthly rates. Inquire within, or check out StayWithNSD Bright and cozy 2-bedroom, ...
Click For Pricing
VRBO
From $1598 per night (USD)
Expedia
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 $1598 per night (USD)
Expedia
From $145 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 $145 per night (USD)
VRBO
From $149 per night (USD)
Expedia
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 $149 per night (USD)
Expedia
From $259 per night (USD)
VRBO
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 $259 per night (USD)
VRBO
From $313 per night (USD)
Expedia
Beachside Condo w/ Stunning Lake Views
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Blue water+White sand+Waves will surely make your stay in our second-floor Waves of Happiness Condo hosted by Sheboygan ...
From $313 per night (USD)
Expedia
From $124 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 $124 per night (USD)
VRBO
From $314 per night (USD)
Expedia
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 $314 per night (USD)
Expedia
From $331 per night (USD)
VRBO
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 $331 per night (USD)
VRBO
From $331 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 $331 per night (USD)
Expedia
$\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy$
From $1004 per night (USD)
VRBO
\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 $1004 per night (USD)
VRBO
From $1010 per night (USD)
Expedia
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 $1010 per night (USD)
Expedia
From $495 per night (USD)
VRBO
Beachside, Chefs Kitchen, High-End Everything
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our "Delightful Seaside Picnic," hosted by Rose and Fern and Sheboygan Vacation Rentals! This newly renovat ...
From $495 per night (USD)
VRBO
From $208 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 $208 per night (USD)
Expedia

Search Your Destination Now!

Sheboygan Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 141 Rentals