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

Sheboygan Rentals

From $671 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 $671 per night (USD)
VRBO
From $336 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 $336 per night (USD)
Expedia
From $442 per night (USD)
VRBO
REMODELED HOME ON LAKE MICHIGAN
Bedrooms:
2
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 $442 per night (USD)
VRBO
$Updated Sheboygan Home w\/ Porch < 1 Mi to Beach$
From $324 per night (USD)
Expedia
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 $324 per night (USD)
Expedia
From $360 per night (USD)
VRBO
Family Home, 1 Block to Lake Michigan Beach!
Bedrooms:
2
Bathrooms:
7
Sleeps:
7
- Game Room - Central Location - Recently Remodeled From Lake Michigan to downtown, there's something for everyone at t ...
From $360 per night (USD)
VRBO
$2 bed\/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub$
From $415 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 $415 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
Click For Pricing
Expedia
Ryder Cup - Premier Location!
Bedrooms:
2
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 $397 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 $397 per night (USD)
VRBO
From $329 per night (USD)
Expedia
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)
Expedia
Click For Pricing
VRBO
Geele Ave Rental for Ryder Cup
Bedrooms:
3
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
VRBO
From $356 per night (USD)
Expedia
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Kohler Design Center Rentals, Kohler Andrae State Park Rentals, Whistling Straits Rentals Blue Harbor Rentals, Road Amer ...
From $356 per night (USD)
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:
3
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:
3
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 $326 per night (USD)
Expedia
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Escape to this spacious downtown riverfront retreat with easy access to nearby beaches, restaurants, and local shopping ...
From $326 per night (USD)
Expedia
From $173 per night (USD)
VRBO
Cozy 2 bd home, minutes from lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Cozy,Clean two bedroom home.Recently renovated. Fully equipped kitchen,fenced backyard for your pets.Walking distance to ...
From $173 per night (USD)
VRBO
From $379 per night (USD)
Expedia
Pet-Friendly Sheboygan Home, 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
6
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 $379 per night (USD)
Expedia
Click For Pricing
VRBO
Fun family home near Ryder Cup
Bedrooms:
3
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
VRBO
From $811 per night (USD)
Expedia
Central located. Seconds from the highway to get to kohler, and Elkhart lake
Bedrooms:
3
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)
Expedia
From $363 per night (USD)
VRBO
Updated Victorian in the Heart of Sheboygan. Beach, Downtown, Golf, Road America
Bedrooms:
2
Bathrooms:
5
Sleeps:
9
Lovingly restored 1890s Victorian home, updated to include the modern amenities you expect. Fully stocked kitchen, with ...
From $363 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
From $452 per night (USD)
VRBO
BEACHVIEW GETAWAY
Bedrooms:
2
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 $452 per night (USD)
VRBO
From $454 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
In this newly renovated landmark home you are walking distance from all that Sheboygan has to offer. Delicious food, nig ...
From $454 per night (USD)
Expedia
From $777 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 $777 per night (USD)
VRBO
From $448 per night (USD)
Expedia
Beachside, Chefs Kitchen, High-End Everything
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Welcome to our "Delightful Seaside Picnic," hosted by Rose and Fern and Sheboygan Vacation Rentals! This newly renovat ...
From $448 per night (USD)
Expedia
From $320 per night (USD)
VRBO
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 $320 per night (USD)
VRBO
From $430 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 $430 per night (USD)
Expedia
From $461 per night (USD)
VRBO
Beachfront Villa - Sleeps 8. Right on the beach!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Welcome to this charming villa in Sheboygan. This gorgeous property boasts 2 bedrooms, including a king bed, queen bed, ...
From $461 per night (USD)
VRBO
From $461 per night (USD)
Expedia
Catch a Wave: Beachfront King Suite - Sleeps 8!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to your perfect getaway! This beautiful beachfront property is located right on the shores of Lake Michigan, off ...
From $461 per night (USD)
Expedia
From $627 per night (USD)
VRBO
Edgewater Villa: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Modern 4BR Courtyard Condo – Steps from the Beach in the "Malibu of the Midwest" Escape to Sheboygan, WI—a hidden gem o ...
From $627 per night (USD)
VRBO
From $461 per night (USD)
Expedia
2-bedroom villa in serene Sheboygan with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Nestled in Sheboygan right on the beach, this delightful villa is the perfect retreat for guests seeking a superb vacati ...
From $461 per night (USD)
Expedia
$Unique 3-bedroom w\/easy access to Lake Michigan waterfront & downtown amenities$
From $653 per night (USD)
VRBO
Unique 3-bedroom w\/easy access to Lake Michigan waterfront & downtown amenities
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Welcome to Chateau Blu, a unique, beautifully appointed lakeview retreat. Nestled just a leisurely five-minute walk ...
From $653 per night (USD)
VRBO
From $288 per night (USD)
Expedia
Charming 4-bedroom house with WiFi and AC in delightful Sheboygan
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This Sheboygan house boasts 4 inviting bedrooms with 3 queen beds and 1 crib. The pleasant and soothing atmosphere will ...
From $288 per night (USD)
Expedia
$Sheboygan Shores - Beach\/Arcades\/9 beds\/Sleeps 12$
From $629 per night (USD)
VRBO
Sheboygan Shores - Beach\/Arcades\/9 beds\/Sleeps 12
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to Sheboygan’s Premier Beachfront Getaway! 🌊🏖️ Steps from the public beach, volleyball, pickleball, parks, ...
From $629 per night (USD)
VRBO
From $336 per night (USD)
Expedia
Charming, Modern Riverfront 2-bedroom South Pier, Sheboygan Condo
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Stay comfortably in Sheboygan at this 2-bedroom condo. The space features 2 lovely queen beds, 2 bathrooms with showers, ...
From $336 per night (USD)
Expedia
From $347 per night (USD)
VRBO
NEW! Harbor Hideaway - Walk to Beach, Dining & Downtown
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Cozy Condo Steps from Sheboygan Harbor – Walk to Beach, Dining & Downtown Perfectly situated just steps from the Sheb ...
From $347 per night (USD)
VRBO
From $627 per night (USD)
Expedia
Edgewater Escape: 4 Bedroom, Sleeps 14!
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
This two-story 4 bedroom/3 bathroom get-away is in close proximity to EVERYTHING, including the boardwalk, harbor and do ...
From $627 per night (USD)
Expedia
From $627 per night (USD)
VRBO
Just Beachy: 4 Bedroom, Sleeps 12!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Newly Renovated 4BR/3BA Upper-Level Condo – Walk to Boardwalk, Harbor & More! Welcome to your perfect home away from ho ...
From $627 per night (USD)
VRBO
From $331 per night (USD)
Expedia
Overlook Oasis - Walk to Lake at Ellis District
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Overlook Oasis by Great Lakes Getaways! Nestled in Sheboygan’s charming and historic Ellis District. This newly remode ...
From $331 per night (USD)
Expedia
From $945 per night (USD)
VRBO
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette weekend, gol ...
From $945 per night (USD)
VRBO
From $155 per night (USD)
Expedia
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)
Expedia
From $702 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 $702 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 $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
From $244 per night (USD)
Expedia
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 $244 per night (USD)
Expedia
$2BR, 1.5BA, Pet-friendly, Lower duplex w\/finished basement + large backyard!$
From $141 per night (USD)
VRBO
2BR, 1.5BA, Pet-friendly, Lower duplex w\/finished basement + large backyard!
Bedrooms:
2
Bathrooms:
3
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 $232 per night (USD)
Expedia
2BR Spacious Upper, Overlooking Kiwanis Park, Close to Everything!
Bedrooms:
1
Bathrooms:
3
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)
Expedia
From $183 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 $183 per night (USD)
VRBO
From $494 per night (USD)
Expedia
Original Art |1904 Classic | Near Beach & Downtown
Bedrooms:
3
Bathrooms:
4
Sleeps:
7
Newly renovated 1904 home in prime location. Remodeled kitchen and baths, gorgeous woodwork and floors, off-street parki ...
From $494 per night (USD)
Expedia
From $777 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 $777 per night (USD)
VRBO
From $269 per night (USD)
Expedia
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 $269 per night (USD)
Expedia
$Sheboygan Getaway w\/ Yard: 1 Mi to Lake Michigan$
From $321 per night (USD)
VRBO
Sheboygan Getaway w\/ Yard: 1 Mi to Lake Michigan
Bedrooms:
1
Bathrooms:
3
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 $321 per night (USD)
VRBO
From $293 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 $293 per night (USD)
Expedia
From $867 per night (USD)
VRBO
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 $867 per night (USD)
VRBO
From $253 per night (USD)
Expedia
Riverfront Townhome with GIANT Rec Room and Private Riverfront Deck
Bedrooms:
2
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 $253 per night (USD)
Expedia
From $345 per night (USD)
VRBO
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 $345 per night (USD)
VRBO
From $477 per night (USD)
Expedia
LUXE Manor with Modern, Elegant Vibes
Bedrooms:
4
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 $477 per night (USD)
Expedia
From $313 per night (USD)
VRBO
Family-Friendly House: Walk to Lake Michigan!
Bedrooms:
2
Bathrooms:
5
Sleeps:
6
Spend fun-filled days with your surfboard when you choose this conveniently located Sheboygan vacation rental! Just unde ...
From $313 per night (USD)
VRBO
From $301 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 $301 per night (USD)
Expedia
From $700 per night (USD)
VRBO
Luxury Villa on Lake Michigan!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Summary: Welcome to the ideal place on Lake Michigan for a family beach getaway, wind surfing, fishing, bachelorette wee ...
From $700 per night (USD)
VRBO
$Beachside Condo w\/ Stunning Lake Views$
From $405 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 $405 per night (USD)
Expedia
From $185 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 $185 per night (USD)
VRBO
From $131 per night (USD)
Expedia
Lake Breeze on 11th
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Sheboygan has lots to offer & our place is perfect for your homebase. The lakefront, Sunrise, End, & Vollrath park are j ...
From $131 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Beachy Bungalow! Come in and unwind at our beachy 3 bedroom upper unit near Lake Michigan, Whistling Str ...
From $176 per night (USD)
VRBO
From $176 per night (USD)
Expedia
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Coastal Comfort! Comfort: noun - a state of physical ease and freedom from pain or constraint Come in a ...
From $176 per night (USD)
Expedia
From $176 per night (USD)
VRBO
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Bedrooms:
1
Bathrooms:
3
Sleeps:
5
Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will u ...
From $176 per night (USD)
VRBO
From $485 per night (USD)
Expedia
NEW! Indigo Waters- Steps to the sand! Sleeps 7! Book today!
Bedrooms:
2
Bathrooms:
2
Sleeps:
7
Indigo Waters by Great Lakes Getaways! Step into this vibrant, updated condo where bold colors and unique touches make ...
From $485 per night (USD)
Expedia
From $289 per night (USD)
VRBO
Steps from Lake Michigan: North Point Place
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Conveniently located for adventure and relaxation along the lakeshore and beyond, this historic home is steps away from ...
From $289 per night (USD)
VRBO
$\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy$
From $1011 per night (USD)
Expedia
\n\nLuxury Downtown Sheboygan 4BR-2.5 Bath - 3 min walk to beach - Lakeside Legacy
Bedrooms:
3
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 $1011 per night (USD)
Expedia
From $268 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 $268 per night (USD)
VRBO
From $152 per night (USD)
Expedia
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 $152 per night (USD)
Expedia
$Eclectic Spacious 3 BR Home Near Lake MI w\/ Fire Pit$
From $187 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 $187 per night (USD)
VRBO
From $471 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 $471 per night (USD)
Expedia
From $132 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 $132 per night (USD)
VRBO
From $321 per night (USD)
Expedia
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 $321 per night (USD)
Expedia
$Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!$
Click For Pricing
VRBO
Apt w\/ Shared Gas Grill, 2 Blocks to Dtwn!
Bedrooms:
1
Bathrooms:
2
Sleeps:
2
Escape to Lake Michigan when you choose this centrally located Sheboygan vacation rental! Bring your fishing rods to spe ...
Click For Pricing
VRBO
Click For Pricing
Expedia
Northside Charmer!
Bedrooms:
3
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
Expedia
Click For Pricing
VRBO
5mi from the Ryder Cup @ Whistling Straits, natural beauty and serenity awaits!
Bedrooms:
3
Bathrooms:
4
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
VRBO
From $335 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 $335 per night (USD)
Expedia
$Sheboygan Getaway w\/ Deck + On-Site Lake Access!$
From $284 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 $284 per night (USD)
VRBO
Click For Pricing
Expedia
Remodeled Cape Cod within steps of Lake Michigan
Bedrooms:
2
Bathrooms:
4
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
$Riverfront Sheboygan Townhome w\/ Grill!$
From $316 per night (USD)
VRBO
Riverfront Sheboygan Townhome w\/ Grill!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Find rest and relaxation where the Sheboygan River flows into Lake Michigan at this 2-bedroom, 1.5-bathroom townhome. Th ...
From $316 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
$Beach Lake House walking disance to lake Close to Downtown\n & South Pier\n4BR 2BA$
From $666 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 $666 per night (USD)
VRBO
From $497 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 $497 per night (USD)
Expedia
$Downtown Sheboygan Apartment w\/ Private Deck!$
From $249 per night (USD)
VRBO
Downtown Sheboygan Apartment w\/ Private Deck!
Bedrooms:
1
Bathrooms:
5
Sleeps:
8
Nestled in the heart of downtown, this 4-bedroom, 1-bathroom Sheboygan vacation rental is a walkable utopia for your nex ...
From $249 per night (USD)
VRBO
From $823 per night (USD)
Expedia
'Beautiful Day Getaway' - Lake Michigan Views
Bedrooms:
3
Bathrooms:
5
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 $823 per night (USD)
Expedia
From $162 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 $162 per night (USD)
VRBO
From $129 per night (USD)
Expedia
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 $129 per night (USD)
Expedia
From $511 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 $511 per night (USD)
VRBO
From $341 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 $341 per night (USD)
Expedia
From $303 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 $303 per night (USD)
VRBO
From $193 per night (USD)
Expedia
Historic Home in Quiet Central Location
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtow ...
From $193 per night (USD)
Expedia
From $301 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 $301 per night (USD)
VRBO
From $461 per night (USD)
Expedia
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 $461 per night (USD)
Expedia
From $358 per night (USD)
VRBO
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 $358 per night (USD)
VRBO
From $555 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 $555 per night (USD)
VRBO
Click For Pricing
VRBO
New! Breezy Beach - 75 Steps to Lake Michigan!
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Breezy Beach by Great Lakes Getaways! This villa is just 75 steps from Lake Michigan’s sandy shores, with fishing, boat ...
Click For Pricing
VRBO
$Shoreline Sanctuary - 4BR Villa w\/ Lake Views, Beach Access & Sunsets$
Click For Pricing
Expedia
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 ...
Click For Pricing
Expedia

Search Your Destination Now!

Sheboygan Rentals

Rental Rates ($USD weekly)

Guests

Check Rates & Availability:

Results: 141 Rentals