Vacation Rentals By Owner In Sheboygan, WI

This fantastic condo in Sheboygan offers two bedrooms with queen beds, perfect for a relaxing getaway. With amenities like WiFi, a washer and dryer, and AC, guests will have everything they need for a comfortable stay. The bathroom comes equipped with a hair dryer for added convenience. This condo is the ideal home base for your trip to Sheboygan. We hope you'll enjoy your stay at our condo.

Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$97.54

Your cozy getaway awaits in Sheboygan at this beautiful upper unit duplex . This nice space features 1 bedroom with a comfortable queen bed, a well-equipped bathroom with a hair dryer, and essential amenities like heating, WiFi, and AC. We think our place will help you experience everything Sheboygan has to offer.

Apartment

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$223.56

Welcome to our beautiful 2-bedroom historic home in Uptown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep.brbrStep inside and be greeted by the character and charm of this 1885 historic home. The living area boasts tasteful furnishings, creating a cozy atmosphere for relaxation after a day of exploring. The fully equipped kitchen provides all the essentials for preparing delicious meals, and a dining area is perfect for enjoying them together.brbrThe bedrooms are thoughtfully designed to provide a peaceful night's sleep. Both rooms feature comfortable king beds with quality linens and ample storage space for your belongings. The clean and modern bathroom offers a refreshing shower and essential amenities.brbrBut the true gem of this property lies in the backyard. Step outside and be transported to your private oasis. The beautifully landscaped yard features a grilling area, perfect for cooking up a mouthwatering barbecue. And when night falls, gather around the outdoor movie screen for a memorable movie night under the stars.br

LUX Uptown Escape - The Trester

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$279.02

Modern/updated 2 bedroom 2 bath townhouse on a quite Cul-De-Sac in Sheboygan, WI. Every part of this house has been remodeled with design and detail in mind. AMAZING kitchen upgrades- Quartz countertops, a custom tile backsplash, stainless steel deep sink and beautiful kitchen faucet...this kitchen will not disappoint! The house also features new plank flooring throughout the first floor along with a floor to ceiling natural stone fireplace for those cool/cozy nights. The main floor includes one bath, living room, dining room and kitchen. The kitchen is fully stocked with all your needs and has all new Stainless steel appliances. Both bathrooms have tiled showers, new flooring and countertops. The two bedrooms both have BRAND New queen size Comfy mattresses and both are located on the second floor with another bath. A custom Rustic wood plank feature wall which includes a barn door to the bath is the first thing you see as you walk up the stairs.. The large deck is right off of the Dining room which looks out into the yard which has a large pond and Hot Tub! It's a nice peaceful country setting in the city.brbrThe house is minutes away from Lake Michigan and all that Sheboygan has to offer. The surrounding areas have so many attractions throughout the year, there is always something to do or see.brbrPopular destinations in the area include:brbr*Sheboygan Riverfront restaurants and shops 4 milesbr*American Club in Kohler 6 milesbr*Black Wolf Run Golf Course 6 milesbr*Historic Elkhart lake which includes Road America 20 milesbr*Whistling Straights Golf Course 12 milesbr*Kohler-Andrae State Park 3 milesbrbr

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$383.06

Welcome to Cozy Corner Cottage — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrThis charming Dutch Colonial house in Sheboygan’s historic Ellis District is just steps away from Deland Park’s beach, offering an ideal family retreat. Featuring three cozy bedrooms, a fully equipped kitchen, and a comfortable living space with entertainment options, it’s perfect for both relaxation and adventure. Enjoy beach access, explore the historic neighborhood, and make unforgettable memories.brbrDiscover timeless charm and modern comfort in this classic Dutch Colonial home, nestled in Sheboygan’s historic Ellis District. Just a short stroll from beautiful Deland Park and Lake Michigan’s sandy shores, this home is the perfect blend of cozy retreat and convenient location — ideal for families, couples, and small groups looking to unwind and explore.brbrWhat you’ll love:brbr✔ Beach AccessbrEnjoy the beach supplies stored in the front closet, perfect for enhancing your time at nearby Deland Park.br✔ Comfortable Living SpacebrThe living room offers ample seating and a smart TV for entertainment, alongside complimentary high-speed WiFi to stay connected during your stay.br✔ Fully Equipped KitchenbrThe kitchen comes with everything you need, from cookware to spices, making it easy to prepare meals at home.br✔ Cozy BedroomsbrUpstairs, three bedrooms provide a restful space for your group. The master bedroom features a queen-size bed with an ensuite half bathroom, while the second bedroom has a twin-over-full bunk bed perfect for children. The third bedroom, also with a queen-size bed, offers plenty of storage.br✔ Relaxing BathroombrChoose between the walk-in shower or a soothing soak in the bathtub, with fresh towels provided for your convenience.br✔ Historic NeighborhoodbrTake a leisurely stroll through the Ellis District and admire the beauty of the neighborhood’s historic architecture, adding a unique charm to your stay.brbrWhether you’re visiting Sheboygan for a fun family vacation or a peaceful beach getaway, our home in the heart of the Ellis District offers a comfortable, convenient, and memorable retreat. Book your stay today and make lasting memories with your loved ones.brbr :brJohn Michael Kohler Arts Center – 1 mile (4 min)brAbove & Beyond Children’s Museum – 1 mile (4 min)brEllwood H. May Environmental Park (Maywood) – 2 miles (7 min)brbr & :brBlack Pig – 1 mile (4 min)brThe Duke of Devon – 1 mile (4 min)brLino Ristorante Italiano – 1.5 miles (6 min)brbr & :brSheboygan Brat Days – AugustbrHoliday Parade – NovemberbrMaywood Earth Ride – MaybrbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

Cozy Corner Cottage - Dutch Colonial Step from Beach

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$474.4

Welcome to Wandering Waves — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrWake up to sweeping Lake Michigan views in this stylish 2BR/2BA beachfront condo! Just steps from the sand, you’ll enjoy sunrise mornings, wave-filled nights, and unbeatable beach access. Inside, a modern open layout offers a fully equipped kitchen, cozy living area, and private patio with serene water views.brbrPerfect for couples, families, or friends, this condo is ideal for a weekend getaway or longer stay.brbrWelcome to your ultimate getaway! This beautifully renovated 2-bedroom, 2-bath beachfront condo offers a serene retreat just steps away from the pristine shores of Lake Michigan. With sweeping views, modern comforts, and a prime location, this is the perfect place for a relaxing and unforgettable vacation.brbr ’ :br✔ Master Suite with King Bed & Jetted TubbrEnjoy ultimate relaxation in the master suite, featuring a king-sized bed and a private en-suite bathroom with a jetted tub, ideal for unwinding after a day at the beach.br✔ Private Queen BedroombrThe second bedroom offers a cozy queen bed, designed for guests who want their own retreat while staying close to all the excitement. Thoughtful design with natural light ensures a peaceful rest.br✔ Fully Stocked Kitchen & Dining Area:brThe kitchen is fully equipped with everything you need to prepare meals, from cookware to utensils. Enjoy breakfast at the bar or share meals around the dining table with stunning lake views.br✔ Cozy Living Room with Gas FireplacebrThe living room is perfect for relaxation, with a gas fireplace to keep you warm. Watch TV, read a book, or simply gaze out the window at the waves crashing on the shore.br✔ Direct Beach AccessbrStep outside and you’re just a few feet from the beach! Spend your days lounging on the sand, collecting shells, or simply enjoying the stunning sunsets over Lake Michigan.br✔ Perfect Location & ComfortbrWith modern amenities and the natural beauty of Lake Michigan right at your doorstep, this condo provides the best of both worlds—luxury and serenity.brbrExplore the SurroundingsbrWhether you're looking to relax on the beach, enjoy scenic walks along the shore, or explore local attractions, this condo offers the perfect base for your Lake Michigan adventure.brbr :br* Deland Park – 0.3 milesbrBeach access, picnic areas, playgrounds, surfing, and the historic Lottie Cooper Shipwreck. Hosts annual kite festivals.br* Sheboygan Marina – 0.3 milesbrBoat rentals, fishing, and scenic waterfront views.br* North Point Park – 0.5 milesbrLake views, walking trails, and peaceful relaxation spots.br* John Michael Kohler Arts Center – 1 milebrContemporary art exhibitions and interactive installations.br* Above and Beyond Children's Museum – 1 milebrHands-on exhibits and educational programs for kids.brbr & :br* Driftwood South Pier – 0.1 milesbrWaterfront bar & grill with American cuisine and river views.br* Lino Ristorante Italiano – 0.2 milesbrUpscale Italian dining with authentic dishes.br* Weather Center Café – 0.2 milesbrSpecialty coffee, teas, and light meals in a cozy setting.br* Field to Fork – 0.9 milesbrFresh, locally sourced breakfast and lunch with bakery and roastery.brbr & :br* Sheboygan Farmers Market – 0.9 milesbrWednesdays & Saturdays (June–October), fresh produce, crafts, and live entertainment.br* Deland Park Kite Festival – 0.3 milesbrAnnual vibrant kite displays and family fun.br* Sheboygan Midwest Challenge – 0.5 milesbrAugust powerboat races with high-speed excitement and festivities.brbr : br- This condo is privately owned and does not include access to the Blue Harbor Resort water park. Guests may not purchase day passes, as the unit owner has waived the Resort Amenity Fee.br- This condo does not have any associated with Blue Harbor, and none of their amenities are included.brbrWe are excited to host you! Your satisfaction and comfort are our top priorities. Book now and experience lakeside living at its finest! Your Perfect Getaway Awaits!brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

Villa

Wandering Waves - Beachfront Lake Michigan Stay!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$207.14

*** STEPS AWAY FROM LAKE MICHIGAN***brbrExperience the vibrant energy from our stylish apartment with great views. Enjoy easy access to the beach, restaurants, bars and a cozy stylish getaway for unforgettable relaxation and adventure. The apartment features fully equipped kitchen, cozy living area, and comfortable bedrooms.brbrYou are in the center of it all, walking distance to Lake Michigan and the Beach, Bars, Restaurants, River Boardwalk, and Historical Downtown.brThe spacebr1st Floor Condo that features living room, 2 bedrooms, 1 bathroom, full kitchen.brbrLiving Room: features TV with internet, pull out sofa bed that sleeps 2, fireplace, plenty of space for sitting.brbrBedroom #1: features TV with internet, queen size bed, luggage stand, closet with hangers, night light for reading, CO/smoke detector.brbrBedroom #2 features queen size bed, luggage stand, closet with hangers, night light for reading, CO/smoke detector.brbrKitchen: Fridge/Freezer, oven, breakfast table, coffee maker, snack bar, cooking utensil set.brbrPlease, No pets or smoking allowed on premise.brGuest accessbrYou will enter the building through a common entrance that leads into the hallway. Once inside, you will have your specific passcode key for keyless entrance.brbrPlenty of street PARKING on both sides of the street.brbrEarly Check in or late Checkout requests could be accommodated, please message for details.brOther things to notebrWhere is Sheboygan brSheboygan, Wisconsin, is 55 miles north of Milwaukee, 60 miles south of Green Bay, 110 miles north of Madison, 140 miles north of Chicago, and a short drive of 340 miles from Minneapolis. Sheboygan is a great stop on your way to Door County, which happens to be 131 miles away.brbrSheboygan is a lovely city situated on the shores ofbrLake Michigan. Visitors and residents alike enjoy Sheboygan’s natural treasures, it’s scenic parks, well-planned recreational opportunities, exciting events, and world-class restaurants and accommodations.brbrEnjoy the serenity of the South Pier District and the Fish Shanty Village Riverfront Boardwalk. Enrich your stay with the enchantment of the John Michael Kohler Arts Center, theaters, museums, antique shops, and charming B&Bs.brbrThere is always something fun to do with a variety of events and activities such as music festivals, boating, biking and the Blue Harbor Resort water park.brbrOne of the most exciting ways to spend the day in Sheboygan is to make a splash at Blue Harbor Resort’s water park, Breaker Bay Waterpark. Waterpark passes are $40 for a full day and $30 for a half day for non-resort guests, but you have nothing to worry about and can stay at our place.brbrSheboygan also offers the excitement of Lake Michigan charter fishing, world-class golf and world-cup sailboat racing.brbrSheboygan is known as the Malibu of the Midwest because it has some of the best waves for surfing on the Great Lakes. Because of this, surfing is a popular sport year-round, especially winter! Even if you’re not a surfer, you can still enjoy the beautiful beaches in Sheboygan, or other water sports like SUP, fishing, and sailing.brbrThere are also plenty of hiking trails of varying skill levels, including an accessible boardwalk trail (Black River Marsh Boardwalk). A nice walking path along Lake Michigan is perfect for a sunrise or sunset walk. A few of the trails go over the sand dunes, like the half-mile Creeping Juniper Nature Trail.brbrThere are 2 miles of Lake Michigan shoreline to choose from, so make sure to bring swimsuits, towels, and sand toys if the weather is nice outside.brbrWisconsin is full of surprisingly diverse state parks, and Kohler-Andrae State Park is the place to go if you’re looking for sand dunes, wildlife, and beach time!brbrBringing good times to life...providing fun for everyone!

Sheboygan Sunrise Beach Stay

Sheboygan, Wisconsin, United States

Bed

1

Bath

6

Sleeps

$264.88

Welcome to Riverside Drift — Presented by Great Lakes Getaways! brbrEscape to this spacious 2BR, 1.5BA Sheboygan retreat! The king suite features a private balcony and cozy fireplace with serene river views. The second bedroom offers two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, in-unit laundry, and plenty of parking with a 2-car garage plus extra space. Minutes from Lake Michigan and downtown!brbrUnwind in comfort at Riverside Drift, a peaceful and spacious 2-bedroom, 1.5-bath retreat overlooking the serene Sheboygan River. Perfect for families, couples, or small groups, this home sleeps up to 6 guests and offers the ideal mix of relaxation, convenience, and unbeatable location on Wisconsin’s Fresh Coast.brWhether you're here for a weekend escape, a family vacation, or an extended stay, Riverside Drift is your perfect home base in Sheboygan.brbrRoom for Everyone — Sleeps 6 ComfortablybrbrThis family-friendly home includes 3 cozy beds and plenty of space to spread out:br- King Suite with a private balcony + fireplace and peaceful river viewsbr- Second Bedroom with Two Queen Beds — perfect for kids, friends, or extra guestsbrbrAmple storage for luggage and clothing during longer staysbrbrA perfect setup for families traveling together or friends enjoying a getaway.brbr- 1.5 Bathrooms + Laundry for Added EasebrEnjoy extra convenience with:brbr- Full bathroom upstairs near both bedroomsbrbr- Half bath on the main level for easy accessbrbr- Upstairs laundry (washer & dryer) — ideal for beach trips and extended staysbrbr- Fully Equipped Kitchen + Open Living SpacebrFeel right at home with everything you need:brbr- Modern, fully stocked kitchen for home-cooked mealsbrbr- Coffee mornings made easybrbr- Cozy living room for relaxing after a day of adventurebrbr- Open-concept layout perfect for quality family timebrbrStress-Free Parking + Attached 2-Car GaragebrNo street parking hassles here!br- Attached 2-car garagebr- Additional parking directly in front of the garagebrbr- Direct walk-in access makes arrival simple in every seasonbrbr- Riverside Views + Cozy Balcony Fireplacebrbr- Step outside to enjoy beautiful Sheboygan River viewsbrbr- Private balcony fireplace for cozy eveningsbrbr- Perfect spot for morning coffee or sunset unwindingbrbr- Peaceful, scenic, and truly relaxing.brbrPrime Location Near Sheboygan’s Best AttractionsbrYou’re just minutes from everything that makes Sheboygan unforgettable:br- Lake Michigan beachesbr- Sheboygan Lighthousebr- Deland Park (pickleball, tennis courts, lakefront trails)br- Sheboygan Riverwalkbr- Downtown dining, shops, and local favoritesbr- Nearby golf courses and outdoor adventuresbrbrSheboygan is known for its lakefront charm, family-friendly atmosphere, and endless vacation opportunities.br- The Perfect Wisconsin Fresh Coast GetawaybrWhether you're visiting for:br- Beach days & sunsetsbr- Pickleball weekendsbr- Festivals & local diningbr- Riverside relaxationbrbr…Riverside Drift has everything you need for a comfortable, memorable stay.brbrBook your stay today and let Great Lakes Getaways host your next Sheboygan adventure at Riverside Drift!brbrRental Agreement Notice:brGuests are required to review and sign a rental agreement prior to check-in. The agreement includes important house rules and stay policies. Booking this property confirms that you agree to review and complete the rental agreement before your stay. Failure to complete the agreement may result in cancellation of the reservation.

At River's Edge - Charming 2BR River Retreat with Garage

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$737.61

Welcome to our Delightful Seaside Picnic, hosted by Rose and Fern and Sheboygan Vacation Rentals! brbrThis newly renovated home offers a serene retreat just steps from Sheboygan’s stunning shoreline (and biggest and best beach in the area) where you can enjoy a sunrise stroll along the sandy beach or a refreshing dip in the lake. brbrNestled in the charming Ellis Historic District, our home is also just a short walk from the vibrant riverfront and downtown area, where you can explore a delightful array of local restaurants, cafes, boutique shops, and entertainment. The road end also offers easy access to the lovely Sheboygan North Pier and lake walk.brbrOur spacious home has been thoughtfully designed for comfort and style, featuring a bright, open floor plan and a beautifully appointed kitchen equipped with modern appliances and ample counter space – perfect for cooking up a feast or hosting dinner with family and friends. Throughout the home, you’ll find unique handcrafted furniture (Beds are hand crafted by the owner, a renowned furniture designer and woodworker), ultra high-end MillerKnoll seating in the living room, and artwork created by local artisans, adding a touch of Sheboygan’s artistic spirit to your stay.brbrThe neighborhood is quiet, safe, and brimming with historical charm. You'll love the tree-lined streets and classic architecture, making it an ideal place for leisurely walks. For those who enjoy an active lifestyle, Sheboygan is known for being incredibly walkable and bike-friendly (we provide the bikes), with scenic trails along the lake and river. During the summer months, hop on the local trolley for a nostalgic ride through town, or rent one of the many available scooters to explore at your own pace. Public bus transportation is also conveniently accessible for easy travel around the area.brbrWhether you’re here for a relaxing beach getaway, a culinary adventure, or to immerse yourself in the local culture, Rose & Fern’s Delightful Seaside Picnic offers the perfect home base for your Sheboygan experience. brbrWe look forward to welcoming you!brbrAfter requesting your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at Rose & Fern's, as well as the refundable security deposit, which you will be able to execute and set up digitally. brbrPlease note that cancellation fee is 3% to cover the credit card transaction fees.

Beachside, Chefs Kitchen, High-End Everything

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$1285.98

✨ Welcome to the Huron House, hosted by Sheboygan Vacation Rentals ✨brbrA beautiful classy remodeled 5-bedroom, 4-bath home just a short walk from Sheboygan’s nicest public beach and the iconic North Pier. Enjoy lake breezes, neighborhood charm, and easy access to dining, shopping, and family fun.brbrbr The HomebrbrBright, open layout with cozy living room + fireplacebrFully equipped kitchenbrLarge dining table for family meals + gamesbrCurated furnishings + thoughtful touches throughoutbrbrbr Office SpacebrDedicated workspace with desk, monitor & printer — ideal for remote workbrbr Bedrooms & Bathroomsbr5 comfortable bedrooms — space for everyonebr4 modern bathrooms — no waitingbrbrbr ‍♂️ Walkable LocationbrbrStroll to:brLake Michigan’s best public beachbrThe North PierbrRestaurants + shopsbrIce cream + coffeebrSeasonal farmers marketbrbrbr Short Drive To:brbr⛳ World-class golf at Kohlerbr Road America auto racingbr ️ Kohler-Andrae State Park + sand dunesbrbrbr What You’ll LovebrbrIdeal for families & groupsbrPeaceful, tree-lined neighborhoodbrStylish + comfortable interiorsbrClose to everything you want to dobrbrWhether your stay is for the beach, the golf course, the race track, or just a quiet getaway — the Huron House is the perfect place to settle in, reconnect, and make memories.br brbrbr✨ We look forward to hosting you!brbr- After booking your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at The Huron House, as well as a refundable security deposit, which you will be able to execute and set up digitally.brbr- Pet Fees: $55/dog per night. Please notify us at booking if you plan to bring a dog. $500/night fine for each animal present if not notified.

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$390.49

Welcome to The Cottage — Presented by Great Lakes Getaways! brbrTake advantage of FLEXIBLE MONTHLY RENTALS—available now through April 30, 2026.brbrEscape to this newly renovated beachfront condo nestled along the serene shores of Lake Michigan. Indulge in modern comforts, soak in breathtaking views, and savor the ease of direct beach entry. Your lakeside sanctuary awaits.brbrExperience comfort and convenience in our clean and spacious beach condo, designed for families, friends, and groups. Located just steps away from the beautiful shores of Lake Michigan, this condo offers the perfect setting for your next getaway.brbr ’ :br✔ Comfortable AccommodationsbrThe primary suite features a luxurious king-size bed and an exclusive en-suite bathroom with a relaxing deep-soak tub—perfect for unwinding after a day of exploring. The second bedroom is family-friendly, with a cozy queen bed and a bunk bed arrangement, making it ideal for groups or families with children.br✔ Convenient BathroomsbrBoth bathrooms are equipped with refreshing showers, complimentary toiletries, and extra towels for your convenience.br✔ Additional Sleeping SpacebrA sofa sleeper in the living room ensures extra sleeping accommodations, allowing the condo to comfortably fit up to 8 guests.br✔ Fully Equipped Kitchen & Dining AreabrThe fully stocked kitchen, complete with modern appliances, ensures effortless meal preparation, while the dining area provides the perfect space to enjoy your meals together.br✔ Steps from the BeachbrEnjoy direct beach access just outside your door—whether you’re lounging on the sand, soaking up the sun, or enjoying a leisurely walk along the shore, Lake Michigan is right at your fingertips.brbr :br* Sheboygan Breakwater Lighthouse — 0.5 miles northeastbrHistoric lighthouse with scenic views, perfect for photos and shoreline walks.br* John Michael Kohler Arts Center — 1 mile southwestbrCultural hub featuring contemporary art exhibits, live performances, and interactive installations.br* Deland Park — 1 mile northeastbrBeautiful lakefront park with picnic areas, playground, volleyball courts, and outdoor activities.br* Sheboygan County Historical Museum — 1 mile southwestbrMuseum showcasing local history and early settler artifacts.br* Road America — 20 miles westbrWorld-famous race track hosting NASCAR, IndyCar, and other major motorsport events.brbr & :br* The Duke of Devon — 1 mile southwestbrCozy British pub with traditional fare and craft beers.br* Lino Ristorante Italiano — 1.5 miles southbrUpscale Italian dining with classic pasta, seafood, and fine wines.br* The Black Pig — 1 mile southwestbrFarm-to-table restaurant offering modern American dishes with locally sourced ingredients.br* Sly's Midtown Saloon — 1 mile southwestbrComfortable tavern serving classic comfort food and drinks.br* Meatball Joe’s — 1.5 miles southbrFamily-friendly spot famous for meatball sandwiches and casual dining.brbr & :br* Sheboygan Brat Days (August)brFestival celebrating German heritage with bratwurst, live music, car show, and fireworks.br* Holiday Parade (November)brFestive parade with floats, marching bands, and community groups.br* Lakefront Music Festival — 1 mile northeastbrFree summer concerts at Deland Park featuring local and regional artists.br* Farmer’s Market — 1 mile southwestbrSeasonal market open Saturdays May to October with fresh produce, crafts, and treats.br* Witches Gulch Fall Festival (October)brAutumn celebration with pumpkin decorating, guided tours, and seasonal snacks.brbr : br- This condo is privately owned and does not include access to the Blue Harbor Resort water park. Guests may not purchase day passes, as the unit owner has waived the Resort Amenity Fee.br- Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.br- Guests can park in the assigned parking space (711), any unmarked spot, or street parking.brbrWe are excited to host you! Your satisfaction and comfort are our top priorities. Book now and experience lakeside living at its finest! Your Perfect Getaway Awaits!

The Cottage - Newly Renovated Beachfront Condo on Lake Michigan

Sheboygan, Wisconsin, United States

Bed

Bath

8

Sleeps

$1879.23

Located on a dead-end street, this 4 bedroom home is less than 15 minutes away from Whistling Straits and many other golf courses and walking distance to Blind Horse Winery. Located just north of Kohler, the Kohler Water Spa and Shops at Woodlake are just 2 miles down the road. brbrThe private backyard is fully fenced in with a deck-great for cooking out. Gas grill and gas bonfire pit included. The perfect setup after a long day at the course. brbrThis home offers a master with an attached full bath and an additional half bath on the main level. There are three bedrooms upstairs along with another full bath. ! Note: the bedroom pictured with a crib will be outfitted with a full size bed. brbrThe three-car garage will fit one vehicle. The remaining space is used for a gym. Feel free to get a workout in while you are here. Don't worry, the driveway offers plenty of additional parking.

Private, 4-bedroom, 2.5-bath near Kohler golf & walking distance to winery!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$264.27

Welcome to Superior Commons by Doorway Travel! This newly renovated and professionally decorated apartment is centrally located; only 4 mins to downtown and 5 mins to the shoreline! Upon entry you are welcomed by a spacious kitchen, dining and living area. Relax and unwind on new memory foam queen mattresses in all bedrooms. 43` Roku TVs in all bedrooms and a 65` Roku TV in the living area. The kitchen is fully stocked for meal prep. Enjoy the coffee & tea bar! We are pet friendly!brbrThe Quad on Superior is a recently remodeled property with four units. Each unit can be rented individually, or all four can be rented to sleep 27 people! brbrThis second-floor unit has three very spacious bedrooms with new memory foam queen mattresses, the largest room has an additional twin memory foam mattress.brbrRoku TVs are available in each bedroom and living area. They are set up in guest mode so you can login to your preferred streaming services. White noise machines are available in each bedroom along with blackout shades to ensure a peaceful nights rest!brbrBedroom 1: Queen bed with new memory foam mattress. 43` Roku TV. Closet for storage. brbrBedroom 2: Queen bed with new memory foam mattress and an additional twin memory foam mattress. 43` Roku TV. Closet for storage. brbrBedroom 3: Queen bed with new memory foam mattress. 43` Roku TV. Closet for storage.brbrBring out your inner chef in the fully stocked kitchen using Greenware pots & pans and silicone utensils. A starter supply of paper towels, dish soap, and toilet paper are provided.brbrEnjoy your morning beverage of choice at the coffee and tea bar! A coffee pot and Keurig are available; we provide a starter set of ground coffee, k-cups, tea, creamer, sugar and stevia. brbrFull bathroom is stocked with shampoo, conditioner and body wash. Makeup towels and a hair dryer are available. brbrFree laundry is available on site; the washer and dryer are located in the basement. For your convenience, laundry detergent and wool dryer balls are stocked in the laundry room!brbrGuests will have access to the entirety of Unit D, along with the general shared hallway spaces in the rest of the building.brbrLocated in a residential neighborhood, across the street from green space next to a commercial building. This building is very conveniently located for walking or driving. Superior Avenue does have regular traffic, so please keep that in mind if you are looking for a very quiet and out of the way location.brbrThis building has only 2 shared parking spaces available off-street. Street parking is available in front of, and next to, building on a first come first serve basis. Street parking is shared with neighbors, so you may not be able to park directly in front of the building.brbr$250 pet fee includes up to 2 dogs. Additional or unauthorized pets will result in an additional $250 per animal. Pet owners must clean up the property after taking their pet outside. A $25 fee will be applied to reservations that require additional cleaning outside after pets.brbrWe are available for guests if needed! Guests will be provided a unique keycode for entry for keyless check-in and check-out at their convenience.brbrIf a guest is under the age of 25, or if most of their group is under the age of 25, they may be required to submit photo IDs of everyone in the group and pay a security deposit for the booking to be approved.brbrCredit card fees are non-refundable upon booking if reservation is cancelled by guest.br- Guests must be 25 years or older to book. br- If a guest is under the age of 25, or if most of their group is under the age of 25, they may be required to submit photo IDs of everyone in the group and pay a security deposit for the booking to be approved.br- Rental Agreement must be signed to receive check-in instructions, including code of entry.br- Government issued photo ID is required for booking to verify identity. br- No parties or events allowed in the home. A $1500 fee will be applied to any bookings that host a party or event, and booking may be terminated immediately without refund. br- No additional guests other than those indicated in the booking allowed, maximum of 7 guests allowed in the home.br- $250 pet fee includes up to 2 dogs. Additional or unauthorized pets will result in an additional $250 per animal. Pet owners must clean up the property after taking their pet outside. A $25 fee will be applied to reservations that require additional cleaning outside after pets.br- A $150 charge applies for lost backup keys.br- No smoking, including vaping, is allowed in the home. A $500 fee will apply for anyone found to have smoked inside the property.br- No candles or open flames allowed in the home. br- Please close and lock all windows and doors when you leave the home.br- Please be respectful of neighbors when using entrances and shared spaces such as hallway and laundry area. Music and noise should be kept to a minimum after 9pm and before 8am.br- Property has exterior cameras for security of guests and property. Cameras capture 360 degree views of exterior property including front, back, and sides of building, and front walkway area. Recording occurs 24/7. No exterior cameras can view any interior spaces. No interior cameras. Tampering or disabling of cameras will result in immediate termination of the reservation.br- Tampering or disabling of wifi will result in immediate termination of the reservation.br- Rearranging furniture in the home that results in damages in the home or labor cost associated with returning furniture to its original location will be charged to the guest after check out.br- Please remove your shoes when in the home.br- Check-out is at 10am unless a late check-out has been previously approved. Check-out past 10am may result in a late check-out fee of $50 per hour if this results in the cleaning team waiting for guest to check-out.br- Please report any problems or issues immediately so we can address these during your stay. Refunds will not be issued after check-out for any problems or issues that were not reported during the stay. br- Any violation of Airbnb terms of service or house rules may result in immediate termination of the reservation. br- Trip insurance is recommended with your stay as the cancellation policy does not include covering for sickness or weather circumstances. Please see Airbnb`s strict cancellation policy for further details.br- We do not refund any credit card fees for reservations canceled by guest.

Apartment

Sleeps 7{SPACIOUS}Pets Welcome!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$629.7

This is your new favorite vacation spot. A spacious, two-level condo located just across the courtyard from the beautiful beaches of Lake Michigan. It's the perfect place to relax, recharge, and enjoy quality time with family and friends. You're close to all the action but can always retreat to your peaceful home away from home.brbrPLEASE NOTE: Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee. Guests and occupants are not permitted to access or attempt to access Breaker Bay Waterpark. Purchasing or attempting to purchase tickets is strictly prohibited. Violations may result in a fine at the owner’s discretion, which will be the guest’s responsibility and must be paid in full.brbrStep inside to a bright and airy open-concept living area, where large windows fill the space with natural light and create a welcoming atmosphere. The main level is a hub for relaxation and connection, featuring a cozy living room, a dining area for shared meals, and a fully equipped kitchen. From here, you can step out onto your private balcony to enjoy a fresh breeze and views of the peaceful courtyard. The beach and lake are located just across the courtyard, making it a quick walk to the water's edge.brbrThis condo offers ample space for everyone, with four spacious bedrooms spread across two levels. The main floor features two inviting bedrooms, while the upper level holds a special treat: a tranquil master suite complete with a jetted soaking tub in its private bathroom. The upstairs also includes a convenient laundry area, so you can pack light and stay fresh.brbrStarter EssentialsbrWe provide a few essentials to help you settle in comfortably. Guests are responsible for purchasing any additional items they may need during their stay. We do not supply beach chairs or beach towels, so please remember to bring your own.brbrExplore Your SurroundingsbrThe location couldn't be better. You're a short walk from the beach and the scenic lakefront path, and surrounded by Sheboygan's best attractions and eateries.brbrBeach & Parks: Quick drive to Deland Park for beach access, playgrounds, and the historic Lottie Cooper Shipwreck. brbrDining: Enjoy waterfront dining at Parker Johns BBQ & Pizza, upscale fine dining at Harry's Prohibition Bistro, a cozy coffee & croffle at eb flo coffee house, or a sweet treat at South Pier Parlor! All located on the boardwalk right next to the resort, or across the river!brbrFun for All: The John Michael Kohler Arts Center, Above and Beyond Children's Museum, and bookworm gardens offer cultural and educational fun just a short distance away.brbrGood to KnowbrAccessibility: This is a two-story condo. There are stairs to the main living area and a second set of stairs to the upper level.brbrParking: Free on-site parking is available for guests.brbrbrWe can't wait to host you! Book your perfect lakeside getaway today. Once booked, check out the Guidebook for some more local recommendations!brbrRental Agreement Required: A separate rental agreement is required to be signed after booking and can be reviewed in advance upon request. The agreement includes standard terms such as house rules, guest responsibilities, and property-specific policies (for example, rules regarding pool/hot tub use, prohibited access to Breaker Bay Water park, and guest liability for damages).brGuests will receive the agreement electronically after booking and must sign within 48 hours to maintain their reservation. Failure to sign will result in cancellation.

Vacation Paradise: 4 Bedroom, Sleeps 14!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$643.59

Modern 4BR Courtyard Condo – Steps from the Beach in the Malibu of the MidwestbrbrEscape to Sheboygan, WI—a hidden gem on the shores of Lake Michigan, famously dubbed the Malibu of the Midwest. Whether you're planning lazy beach days in the summer or chasing winter waves at one of the country’s top cold-weather surf spots, this stylish, courtyard-facing condo puts you in the heart of it all.brbrThis spacious, two-story, 4-bedroom, 3-bathroom retreat is just steps from the sand and within walking distance of Sheboygan’s charming boardwalk, scenic harbor, and buzzing downtown restaurants. Relax and recharge in this beautifully updated space, ideal for families, groups, or anyone seeking a lakeside escape.brbrYou’re also just a quick 30-minute drive to:brbrWhistling Straits – championship golf at its finestbrbrKohler Spa – world-renowned luxury and relaxationbrbrRoad America – high-speed thrills and motorsport actionbrbrPlease note:brbrThis unit faces the peaceful interior courtyard (no lake view, but a quieter setting).brbr****Renters and guests of this condominium unit do NOT have access to or use of the Blue Harbor Resort water park and WILL NOT TRY TO PURCHASE a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.****brbrWhether you're here for surf, sun, or snowy adventures, you'll love calling this luxury condo your home base in Sheboygan.brbrStarter essentials are provided to help you settle in comfortably. This includes 2 rolls of toilet paper per bathroom, 1 paper towel roll, 2 dishwasher pods, a small bottle of dish soap, a sponge, 2 laundry pods, bath towels, fresh linens, and a few garbage bags. Guests are responsible for purchasing any additional items they may need during their stay. Please note: we do not supply beach chairs or beach towels, so guests should bring their own.

Edgewater Villa: 4 Bedroom, Sleeps 14!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$225.81

Peaceful bohemian retreat filled with warmth and a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! brThe house is spacious with 4 bedrooms (3 Queen beds, 1 Full, 1 Bath) with a well stocked kitchen, inviting dining area, cozy living space, comfy beds, a front porch and a fenced in backyard! Enjoy a cup of coffee, listen to a record or relax on the hammock. We supply a French press coffee maker as well as a 6 cup coffee maker. Lots of coffee for all your mornings and a grinder to keep it fresh.brIf you have a hunger spot we also have snacks and microwave popcorn for our guests to enjoy!brCome and hang out outside!!! brWe have a lovely fenced in backyard, grill for outdoor cooking, a fire pit (we don’t supply wood but you are welcome to get some just down the street at Trillings the local hardware store) and a corn hole game to enjoy! We have a picnic area and gazebo as well for guests enjoyment. brbrWe also provide 4 beach chairs, beach towels an inflatable paddle board ( and life jackets) to use. If you would like to to bike around let us know!! We provide 2 beach cruisers and a kids trailer!brbrOur neighborhood is a safe and family friendly . It has has lots of architectural charm from Dutch and German settlers. It is very walkable with multiple parks nearby and close to downtown. The house is a 3 minute drive or short bike ride to the Sheboygan's beautiful lakefront. Take a dip in Lake Michigan, watch the local surfers catch some waves or enjoy the ever changing sunset! brWhatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!brbrbrFeel the vibes of the Third Coast and cherish the days!!brbrThings that we ask when booking, Guidelines for the house:brbr*Please respect of our home!br*No smoking, parties or candles. *No additional guests unless communicated with us. No weapons allowed on property. No drugs allowed on property. No smoking or tobacco of any kind. (If there is any evidence we will charge a $375 fee)brbr*Please take off shoes when entering our home. (No shoes inside) We recently refinished our floors ourselves so it has been quite the labor of love.brbr*Up to 2 well behaved dogs are allowed. $150 pet fee. Please bring a crate for them when you have to head out)br brbr*Please be respectful of our neighbors, we are in a family friendly neighborhood.brbr*Quiet hours from 9pm-8am.brbr*Also Failure to follow check out instructions and VRBO standard of “Leaving the listing in the condition it was received” will result in an additional $110 /hour cleaning fee. If a pet or person damages any part of the property a $375 fee will be charged.

Good Vibes on the Third Coast-Pet Friendly! Cozy and Close by!

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$289.9

Welcome to the Uptown Coach House, hosted by Sheboygan Vacation Rentals.brbrOur newly built coach house is nestled in the heart of downtown Sheboygan near all the action and some of our finest dining options. You will also find our most Fabulous North Beach to be just a 1/2 mile away.brbrThis upscale and exquisite retreat boasts a unique design aesthetic, featuring curated art, furniture, and decor sourced, literally . . . from around the world.brbrWith two bedrooms and one luxurious bathroom (think high-end Kohler), this coach house offers comfort and style for up to four guests. Each bedroom is thoughtfully decorated to provide a cozy and inviting atmosphere, ensuring a restful night's sleep.brbrThe open-concept living area is the perfect place to relax and unwind after a day of exploring all that Sheboygan has to offer. The living room features plush seating and a smart TV.brbrPrepare delicious meals in the fully equipped kitchen, complete with modern high-end appliances and sleek countertops. Enjoy dining at the stylish dining table, or take advantage of the beautiful weather and walk down the street to some of Sheboygan's most well known restaurants.brbrConveniently located in downtown Sheboygan, our coach house is just steps away from an array of shops, restaurants, and the River Front. Plus, you're less than half a mile away from the stunning shores of Lake Michigan and its beautiful beach. Whether you're here for business or leisure, you'll find everything you need for a memorable stay right at your fingertips.brbrBook your stay today and experience the perfect blend of luxury, convenience, and natural beauty at our stunning coach house in downtown Sheboygan!brbrAfter requesting your reservation, you will receive a notification and link to complete our Rental Agreement, confirming the terms and conditions of your stay at the Uptown Coach House, as well as the refundable security deposit, which you will be able to execute and set up digitally.brbrDisclosure: We do have a Nest Doorbell Cam to monitor the front entry way and for delivery personnel. We also have a Nest Cam on our balcony which monitors the front walk leading up to the home.

Guest House

Downtown, Uniquely Designed, Near the Beach

Sheboygan, Wisconsin, United States

Bed

Bath

Sleeps

$312

Welcome to your Lake Michigan getaway - a bright, modern condo sitting right on Sheboygan's sandy shore line. Wake up to panoramic sunrise views, walk barefoot to the beach, and relax to the sound of gentle waves. brbrThis 2 bedroom, 2 bath beachfront condo combines comfort with Wisconsin lakefront charm - perfect for families, couples, or business travelers seeking a peaceful retreat. Sleeps 7, features 2 beds, 1 bunk bed and 1 roll-away bed. Max of 4 adults and up to 4 kids. Beach Blues is a handicap-accessible condo. brbrPlease note:br- This condo is privately owned and does not include access to the Blue Harbor Resort water park. Guests may not purchase day passes, as the unit owner has waived the Resort Amenity Fee.brbr- Renters and guests of this condominium unit do not have access to or use of the Blue Harbor Resort water park and amenities, and will not try to purchase a Day Pass, since the unit owner obtained a waiver of the Resort Amenity Fee.brbrbrSheboygan is considered the Freshwater Capital of the World. On the Wisconsin shore of the magnificent Lake Michigan, you can enjoy breathtaking views of the lake and its sunrises, making it the perfect destination for a romantic seaside escape. brbrNearby Attractions: br- Deland Park – Beach access, picnic areas, playgrounds, and annual kite festivals.br- Sheboygan Marina – Boat rentals, fishing, and scenic waterfront views.br- North Point Park – Lake views, walking trails.br- John Michael Kohler Arts Center – Art exhibitions.br- Above and Beyond Children's Museum – Hands-on exhibits and programs for children.br- Harbor Centre Marina – Boat rentals, fishing, and waterfront views.br- South Pier Parlor – Ice cream, mini-golf, and arcade games; popular for families.br- Sheboygan Midwest Challenge (August) - Power boat races and family fun.br- Kohler's 5 star PGA championship golf coursesbr- Kohler Andrae State Park - majestic sand dunes, miles of golden beach, shimmering blue Lake Michigan waterbr- Road America - Motorsport permanent race track, family funbr- Green Bay Packers brbr**This condo is not part of Blue Harbor Resort and therefore the resort amenities are not included.

Fits 7! Beachfront Condo - Handicap Accessible

Sheboygan, Wisconsin, United States

Bed

Bath

7

Sleeps

$888.64

Experience the charm of our cozy home away from home!brbrComfortably situated halfway between Milwaukee & Green Bay, it is the perfect spot for families, golfers, race fans, anglers and all sports fans. brbrCharter Hill Retreat is tucked away in a quiet neighborhood, yet close to world class golf, 5 star Kohler restaurants & shopping, endless beaches (surfing anyone ), charter fishing and Road America. brbrUnwind and enjoy the huge private backyard, perfect for your morning coffee, bonfire with s'mores or dinner under the stars!brbrYour getaway awaits in Sheboygan at this brilliant house. With 4 bedrooms including 1 king, 2 queen, and 1 full bed, this amazing property offers plenty of space for guests to relax. With 2.5 bathrooms, getting ready for your weekend events will be a breeze!

Boho Farmhouse - Fire Pit - Huge Backyard-Golfing - Family Friendly

Sheboygan, Wisconsin, United States

4

Bed