Sheboygan holiday rentals

We found 427 holiday rentals — enter your dates for availability
Select from 95 houses, 27 flats and other holiday rentals to find the perfect place for your stay in Sheboygan. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for hanging out with the people that matter most, such as Wi-Fi and cable TV. You'll be sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Sheboygan

Showing deals for:11 Dec - 18 Dec

Pool
Interior
Interior
Step into a world of endless adventure and boundless freedom as you step into the backyard of your dreams. Here, amidst the vast expanse of lush greenery and under the open sky, there's plenty of room to roam and play outdoor games to your heart's content. With sweeping views stretching for miles across the shimmering waters of Lake Michigan, every moment feels like a chapter f...
Exceptional
(47 reviews)

Amazing Luxury Mansion ~ Indoor Pool ~ Stunning Lake Views ~ One Of A Kind!

Newton

12% off
AU$39,858
for 7 nights, 1 home
AU$5,694 per night
includes taxes & fees
Amazing Luxury Mansion ~ Indoor Pool ~ Stunning Lake Views ~ One Of A Kind!
Twinkling string lights lead to the outdoor fire pit for magical nights outdoors.
Four-season room w/ bar seating, great for gathering year-round.
Settle in by one of two wood fireplaces for a cozy cabin night.
Four-season room ready for games, lounging, and laid-back fun.
Exceptional
(54 reviews)

Beach Access near Kohler-Andrae

Oostburg

11% off
AU$4,632
for 7 nights, 1 cabin
AU$662 per night
includes taxes & fees
Beach Access near Kohler-Andrae
Living area
Living area
Private kitchen
Outdoor dining
Exceptional
(15 reviews)

House Neighboring Road America and the Mullet River

Plymouth

9% off
AU$12,434
for 7 nights, 1 home
AU$1,776 per night
includes taxes & fees
House Neighboring Road America and the Mullet River
Interior
Private kitchen
Living area
Interior
Exceptional
(26 reviews)

Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake

Elkhart Lake

12% off
AU$11,252
for 7 nights, 1 home
AU$1,607 per night
includes taxes & fees
Vacation In STYLE! 2 minutes to Road America, Beach, Golf, Downtown Elkhart Lake
Exterior
Property grounds
Terrace/patio
Private kitchen
Exceptional
(41 reviews)

Road America Adjacent Lake House with indoor pool

Plymouth

8% off
AU$7,487
for 7 nights, 1 home
AU$1,070 per night
includes taxes & fees
Road America Adjacent Lake House with indoor pool
Large prep & serving island ideal for cooking or gathering.
Breakfast area framed by forest & lake views for peaceful mornings.
Sconie Skies are gorgeous in every season!
Professionally designed living space blending style & comfort for easy relaxing.
Exceptional
(31 reviews)

Pristine Beach Access, Arcade near Kohler-Andrae

Oostburg

10% off
AU$3,149
for 7 nights, 1 cottage
AU$450 per night
includes taxes & fees
Pristine Beach Access, Arcade near Kohler-Andrae
Exterior
Private kitchen
Living area
Property grounds
Exceptional
(10 reviews)

Peaceful 4 BDRM Lake Michigan Retreat - Perfect for Friends and Families

Sheboygan

8% off
AU$4,871
for 7 nights, 1 home
AU$696 per night
includes taxes & fees
Peaceful 4 BDRM Lake Michigan Retreat - Perfect for Friends and Families
Kitchen & dining area connected by a convenient passthrough bar.
Morning walks on the beach are encouraged.
Warm, beautifully styled dining room made for shared meals & memories.
Spacious family room w/ plenty of seating for everyone to gather & relax.
Exceptional
(98 reviews)

Rare Find! Huge Beach & Luxe Woodsy Cabin

Oostburg

10% off
AU$3,843
for 7 nights, 1 cabin
AU$549 per night
includes taxes & fees
Rare Find! Huge Beach & Luxe Woodsy Cabin
Large sandy beach located 0.2 miles from Sheboygan Shores!
Fully stocked and appointed kitchen for hosting groups.
Kohler Waters Spa - incredible!
Sheboygan Shores mud room.
Exceptional
(10 reviews)

Sheboygan Shores

Sheboygan

8% off
AU$4,071
for 7 nights, 1 home
AU$582 per night
includes taxes & fees
Sheboygan Shores
Fully stocked and updated kitchen with dishwasher, double oven
Lakefront Trail. A walking/biking trail 200 feet from your front door.
Exterior
Living area
Exceptional
(7 reviews)

Steps from Lake Michigan: North Point Place

Sheboygan

12% off
AU$2,683
for 7 nights, 1 home
AU$383 per night
includes taxes & fees
Steps from Lake Michigan: North Point Place
Main level great room
Great room viewed from the loft
Main level bedroom with king size bed, glider, and walk-in closet
Loft area overlooking great room
Exceptional
(63 reviews)

Cozy Cabin in the Woods with fishing and golf nearby

Valders

24% off
AU$2,137
for 7 nights, 1 home
AU$305 per night
includes taxes & fees
Cozy Cabin in the Woods with fishing and golf nearby
Room
Exterior
Private kitchen
Living area
Exceptional
(8 reviews)

Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!

Plymouth

8% off
AU$7,487
for 7 nights, 1 home
AU$1,070 per night
includes taxes & fees
Large Farmhouse near RA & golf. Breakfast Included with lots of room for all!
Exterior
Your new favorite indoor coffee spot.
One of two main floor living room areas flows directly to kitchen for convenience.
Serveware for 10.
Exceptional
(11 reviews)

Modern | Beachfront | Sleeps 10

Oostburg

12% off
AU$5,641
for 7 nights, 1 home
AU$806 per night
includes taxes & fees
Modern | Beachfront | Sleeps 10
Living Room
Street view with Front porch and Garage
Dining Room, Breakfast Bar and Kitchen
Master Bedroom with balcony and Lake Michigan view!
Exceptional
(264 reviews)

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Sheboygan

7% off
AU$1,695
for 7 nights, 1 home
AU$242 per night
includes taxes & fees
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Living Room
Front Deck
Living Room
Kitchen with all new appliances.
Exceptional
(28 reviews)

Lime Ridge Guest House

Elkhart Lake

13% off
AU$3,805
for 7 nights, 1 home
AU$544 per night
includes taxes & fees
Lime Ridge Guest House
Private kitchen
Outdoor dining
Marina
Dining
Exceptional
(81 reviews)

Beach and Golf House

Sheboygan

8% off
AU$3,855
for 7 nights, 1 home
AU$551 per night
includes taxes & fees
Beach and Golf House
Down back dock with view of sunken diving platform...kids' favorite
Dusk view from porch
Exterior
30' screened porch with bar
Exceptional
(61 reviews)

Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf

Plymouth

9% off
AU$3,936
for 7 nights, 1 home
AU$562 per night
includes taxes & fees
Family Fun on Crystal Lake Island - minutes to Road America, hiking, PGA Golf
Open Concept
Outdoor dining
Interior
Interior
Exceptional
(137 reviews)

Book an autumn vacation to Surfdaze!

Oostburg

8% off
AU$2,718
for 7 nights, 1 cottage
AU$388 per night
includes taxes & fees
Book an autumn vacation to Surfdaze!
Interior
Screened porch and view - updated photo as of June 2022
Foyer and start of kitchen
Exterior
Exceptional
(13 reviews)

Remodeled lake house on Lake Michigan, near Kohler

Oostburg

9% off
AU$12,129
for 7 nights, 1 home
AU$1,733 per night
includes taxes & fees
Remodeled lake house on Lake Michigan, near Kohler
Entrance to bedroom three with two twin beds
Living room/dining room
Upper level of Duplex with private side entrance
Kitchen
Exceptional
(21 reviews)

Super clean amazing location downtown Elkhart Lake

Elkhart Lake

8% off
AU$5,087
for 7 nights, 1 home
AU$727 per night
includes taxes & fees
Super clean amazing location downtown Elkhart Lake
Close to the beach & north pier.
Tasteful lake-inspired color palette adds calm, inviting vibes.
Kitchen opens directly into the dining room for effortless hosting.
Convenient open floor plan connecting dining & living rooms.
Exceptional
(7 reviews)

Walk to Beach & Pier | Fully-Loaded Kitchen

Sheboygan

10% off
AU$3,923
for 7 nights, 1 home
AU$560 per night
includes taxes & fees
Walk to Beach & Pier | Fully-Loaded Kitchen
Exterior
Property grounds
Interior
Private kitchen
Exceptional
(20 reviews)

Amazing Lakefront house

Port Washington

8% off
AU$7,890
for 7 nights, 1 home
AU$1,127 per night
includes taxes & fees
Amazing Lakefront house
Interior
Dining
Living area
Room
Exceptional
(8 reviews)

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Sheboygan

8% off
AU$1,565
for 7 nights, 1 home
AU$224 per night
includes taxes & fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Interior
Living area
Private kitchen
Exterior
Exceptional
(7 reviews)

Lake House-Kayaks/Paddle Boards/Private Pier

Plymouth

11% off
AU$4,746
for 7 nights, 1 home
AU$678 per night
includes taxes & fees
Lake House-Kayaks/Paddle Boards/Private Pier

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Explore the waterfront setting in Sheboygan

The area's museums and art galleries are just some of the reasons to come on holiday to Sheboygan. Renowned for its lake, beaches and restaurants, this city welcomes all visitors. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Sheboygan

Are you hoping to find attractions to visit while you're in the area? Venture out of your holiday home and check out everything that makes Sheboygan a one-of-a-kind holiday spot. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Blue Harbor Resort & Conference Center Water Park (0.4 mi / 0.6 km)
  • Blackwolf Run (3.5 mi / 5.6 km)
  • The Bull at Pinehurst Farms Golf Course (5.7 mi / 9.1 km)
  • Whistling Straits Golf Course (7.1 mi / 11.4 km)
  • Road America (14.2 mi / 22.9 km)
  • Evergreen Golf Course (12.3 mi / 19.8 km)

Exploring the beaches and other natural features in Sheboygan

Travellers enjoy Sheboygan for its lakeside setting and riverfront. Whether you're an outdoor enthusiast or just want to appreciate the scenery, Sheboygan is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Bookworm Gardens (2.2 mi / 3.5 km)
  • Elkhart Lake (16.4 mi / 26.5 km)
  • North Side Municipal Beach (0.6 mi / 1 km)
  • Kohler Park Dunes State Natural Area (5.8 mi / 9.4 km)
  • Crystal Lake (15.7 mi / 25.2 km)
  • Cedar Lake (16.5 mi / 26.6 km)

Seasonal weather averages in Sheboygan

If you're planning a holiday around the weather, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

Frequently asked questions

What is the best area to stay in Sheboygan when booking a holiday rental?
When considering a holiday rental in Sheboygan, Wisconsin, the best area to stay is along the scenic Lake Michigan shoreline, particularly in the North Point neighbourhood. This area is known for its beautiful beaches and waterfront parks, making it an ideal spot for those looking to relax and enjoy outdoor activities. The North Point neighbourhood is home to a variety of properties, offering options from charming cottages to modern apartments, ensuring something for every taste.One of the top attractions nearby is the John Michael Kohler Arts Centre, which showcases a diverse range of contemporary art and offers engaging community programmes. Additionally, the Sheboygan Breakwater Lighthouse provides a lovely backdrop for leisurely walks and stunning views of the lake, superb for capturing memorable photographs.
Where are the best areas for renting a beach house in Sheboygan?
For renting a beach house in Sheboygan, the area along North Beach is an excellent choice. This picturesque stretch offers easy access to sandy shores and is popular for its stunning views of Lake Michigan. Many properties here come equipped with amenities such as outdoor decks, fire pits, and spacious living areas, making them ideal for families or groups looking to enjoy a relaxing beach getaway.Additionally, the nearby Deland Park area features charming rental options, often with private gardens and barbecue facilities, great for outdoor dining and relaxation after a day at the beach. Visitors can also take advantage of the local parks, walking trails, and the vibrant setting of the waterfront, which hosts events and provides recreational opportunities.For those interested in exploring further, the Sheboygan Riverfront is another attractive location, with rentals that offer proximity to waterfront dining and local attractions. Many properties in this area include modern kitchens, Wi-Fi, and convenient access to water sports and fishing activities, enhancing the overall holiday experience. Find your rental near the beach in Sheboygan.
What is the most popular type of holiday rental accomodation in Sheboygan?
In Sheboygan, holiday houses are the most popular type of holiday rental, with approximately 248 available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and often include outdoor spaces such as patios or gardens, superb for families or groups looking for a comfortable retreat. Additionally, there are around 116 condos and 104 apartments, which offer more compact living arrangements with essential amenities like kitchen facilities and living areas, suitable for couples or smaller groups. Cottages, with about 48 options, provide a charming, rustic experience, while a selection of 16 villas offers a more luxurious stay.
Are there any family house rentals in Sheboygan?
In Sheboygan, Wisconsin, there are numerous family-friendly house rentals available—around 90 to choose from. This charming lakeside city offers a variety of properties suitable for families, particularly in neighbourhoods close to the waterfront and nearby parks. Many homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor spaces where children can play safely.Visitors can enjoy easy access to attractions like the picturesque Kohler-Andrae State Park, which is great for hiking and enjoying nature, as well as local beaches along Lake Michigan for swimming and sunbathing. Additionally, families can explore the vibrant downtown area, where local shops, restaurants, and cultural sites await.
Can I rent a holiday home with a pool or hot tub in Sheboygan?
In Sheboygan, there are several holiday homes available for rent that feature pools and hot tubs, providing a great option for travellers looking to enjoy some relaxation during their stay. This charming city, located along the shores of Lake Michigan, offers a variety of neighbourhoods where these properties can be found, including the scenic areas near the lakefront and the more residential districts.Rentals often come equipped with amenities such as private pools, outdoor hot tubs, and spacious patios, ideal for both sunbathing and evening gatherings. Many homes also feature fully equipped kitchens, allowing guests to prepare meals and enjoy dining al fresco.
Are there pet-friendly house rentals in Sheboygan?
In Sheboygan, there are a variety of pet-friendly house rentals available, with around 43 options to choose from. Many of these properties are conveniently located near the beautiful shores of Lake Michigan, providing easy access to scenic beaches and waterfront parks. Travellers can expect a range of amenities in these rentals, including fully equipped kitchens, spacious living areas, and outdoor spaces such as patios or gardens, ideal for enjoying time with pets.The city boasts pet-friendly parks, such as Deland Park, which features walking paths, open green areas, and access to the beach, making it a great spot for pet owners to relax and enjoy the outdoors. Additionally, the nearby Kohler-Andrae State Park offers hiking trails and natural landscapes, great for adventurous outings with furry friends.
Are there any remote work holiday rentals in Sheboygan?
In Sheboygan, Wisconsin, there are numerous options for remote work holiday rentals, with around 468 available throughout the area. This vibrant lakeside city offers a variety of properties, including charming cottages, modern apartments, and spacious homes that cater to remote workers. Many of these accommodations come equipped with essential amenities such as free Wi-Fi, dedicated workspaces, and comfortable living areas, ensuring a productive environment for those working remotely.The city is known for its beautiful waterfront, with easy access to Sheboygan's scenic parks and the stunning shores of Lake Michigan. Nearby attractions include the John Michael Kohler Arts Centre and the Sheboygan County Historical Museum, providing opportunities for leisure during breaks. Additionally, local cafes and restaurants are within reach, offering a great change of scenery for remote working. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Sheboygan?
In Sheboygan, popular holiday rental amenities include fully equipped kitchens, which allow guests to prepare their own meals, making it a convenient choice for families or those looking to save on dining out. Onsite parking is often available, providing ease of access for travellers with vehicles. Many properties also come with coffee and tea makers, ensuring guests can enjoy a warm beverage at their leisure. Additionally, rentals frequently feature decks or patios, great for relaxing outside and enjoying the local scenery. Some accommodations also include blenders, suiting those who enjoy making smoothies or other blended drinks during their stay.
When is the best time to visit Sheboygan for a holiday rental?
The most popular time to visit Sheboygan is during the peak season, which runs from May to July. This vibrant period attracts a multitude of travellers eager to bask in the beauty of Lake Michigan and indulge in a variety of outdoor activities. With pleasant temperatures typically ranging from 10 to 25 degrees Celsius, the climate is superb for enjoying the stunning beaches, engaging in water sports, or exploring the picturesque parks that dot the area.May, in particular, is an excellent month to visit, as it marks the beginning of the summer season and offers a delightful atmosphere for outdoor adventures. As the weather warms up, visitors can partake in activities such as hiking along scenic trails, biking through the scenic routes, or simply relaxing by the lake, all while surrounded by the blossoming flora of spring.For those looking for a more budget-friendly option, consider planning your trip in November. While this month is less crowded, it still offers a unique charm with the crisp fall air and the opportunity to witness the beautiful transition into winter. This quieter time allows for a more relaxed exploration of Sheboygan's attractions, and you can still enjoy local dining and art events without the hustle and bustle of peak season.Ultimately, whether you choose the vibrant peak months for lively festivities or the serene atmosphere of November, Sheboygan has something special to offer.
What are the top attractions in Sheboygan?
In Sheboygan, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local culture. The picturesque Lake Michigan shoreline offers scenic views and opportunities for water activities at places like Kohler-Andrae State Park, where guests can explore sandy beaches and walking trails. The Riverfront District is a vibrant area featuring charming shops, restaurants, and art galleries, making it a great spot to experience the local community.For those interested in history, the Sheboygan County Historical Museum presents engaging exhibits about the region's past. Additionally, the John Michael Kohler Arts Centre is a must-visit for art enthusiasts, showcasing a diverse range of contemporary and folk art.
Are all fees included in the Sheboygan holiday homes prices shown on Stayz?
Stayz provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Sheboygan holiday homes with parking?
Stayz offers a wide selection of holiday homes in Sheboygan with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Sheboygan holiday homes?
You can find great discounts on holiday homes in Sheboygan on Stayz, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Sheboygan holiday home booking on Stayz?
To find Sheboygan holiday rentals with free cancellation, just use Stayz's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Sheboygan?
A long-stay holiday home in Sheboygan is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Sheboygan holiday home?
Book your Sheboygan holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Sheboygan?
Prices for holiday homes in Sheboygan vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Sheboygan to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas