Find short term rentals in Sheboygan, WI at the best prices
219 available short term rental offers
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Price per night
Accommodation type
Rating
Best Short term and Weekly rentals in Sheboygan, WI
9.8 15 reviews
Sheboygan, WI
06/08 – 09/08
$500/nighttotal: $1500 (3 )
3 Blocks From Lake Walk To Lake, Guest House 1 Bdrm Full Bath 4 Min To Downtown
1 2
apartment , Sheboygan
This one-bedroom flat is situated in downtown Sheboygan, a short 100-metre walk from St. Peter Claver Parish and approximately 1.3 kilometres from Lake Michigan, placing it near attractions such as the Above & Beyond Children's Museum and Blue Harbor Resort & Conference Centre Water Park. Guests can enjoy a private terrace with outdoor furniture and a fire pit, alongside a fully equipped kitchen, in-unit laundry facilities, air conditioning, and on-site parking, with opportunities for jet skiing, kayaking, hiking, and biking nearby.
8.8 3 reviews
Sheboygan, WI
25/07 – 26/07
$357/nightfor 1 night
Apartment Centrally Located
2 3
apartment , Howards Grove
This two-bedroom flat in Plymouth, located 27 kilometres from Wilke Lake, offers convenient access to Lake Michigan, which is a 17-minute drive away, and is also close to attractions such as the Kohler Design Centre and Whistling Straits Golf Course. This accommodation for four guests features Wi-Fi, air conditioning, a balcony, and on-site laundry facilities, with towel and linen changes available upon request.
10 1 review
Sheboygan, WI
10/08 – 13/08
$356/nighttotal: $1068 (3 )
Storybook 2-bedroom Apartment 1mi From Lake Michigan
2 2
apartment , Sheboygan
This creatively decorated, private lower-level flat, named 'Fox & Folly', offers a unique storybook adventure in Sheboygan, located in a peaceful neighbourhood just 1.6 kilometres from South Beach, North Beach on Lake Michigan, and the Sheboygan Pier, with Bookworm Gardens also nearby. This two-bedroom, one-bathroom apartment accommodates up to five guests with a king-size bed in the master, a full-over-twin bunk in the second bedroom, a fully stocked kitchen featuring a Keurig coffee bar and reverse osmosis filtered water, air conditioning, on-site parking, and a private fenced backyard with a fire pit, plus exclusive access to a shared basement game room.
10 12 reviews
Sheboygan, WI
20/09 – 25/09
$262/nighttotal: $1310 (5 )
Vacay Vibes
1 4
apartment , Sheboygan
This three-bedroom, two-bathroom flat in Sheboygan offers a residential street location with easy walking access to dining, shopping, and entertainment, situated just 1.6 kilometres from the beach. This pet-friendly accommodation for six guests boasts a fully equipped kitchen, air conditioning, a garden with a fire pit, and keyless entry, providing a comfortable base for exploring Sheboygan.
10 19 reviews
Sheboygan, WI
10/08 – 13/08
$323/nighttotal: $969 (3 )
Historic Lower Unit Near Downtown, King/queen Beds
1 2
apartment , Sheboygan
This centrally located apartment in Sheboygan is 1.6 kilometres from the beach, a 10-minute walk to local bars and eateries, and a 3-minute drive to downtown restaurants and shops, offering historic charm with high, detailed ceilings and stylish restored interiors. This four-bedroom, two-bathroom flat accommodates up to six guests with a King bed, Queen bed, and a sleeper sofa, featuring a fully stocked kitchen, on-site laundry, off-street parking for two vehicles, complimentary WiFi, and central heating and air conditioning.
9.3 3 reviews
Sheboygan, WI
24/07 – 26/07
$5025/nighttotal: $10050 (2 )
Lovely Home Located In The Pine Hills Subdivision.
1 3
apartment , Kohler
This four-bedroom house is situated in the Pine Hills Subdivision in Sheboygan, just 9 kilometres from the renowned Whistling Straits Golf Course and a short drive from Highways 23 and 43. This property has received excellent ratings for its location, cleanliness, and overall experience. The house has three bathrooms, providing ample space for up to 10 guests. It offers a fully equipped kitchen, a garden, a fitness centre, air conditioning, parking, and a basement with additional living space.
9.8 6 reviews
Sheboygan, WI
24/07 – 26/07
$685/nighttotal: $1370 (2 )
Newly Updated! Downtown & Shore
3 3
apartment , Sheboygan
This apartment is located in a quiet residential neighbourhood in Sheboygan, just 6.4km from the city centre and 8km from the Lake Michigan shoreline. It has received excellent user ratings, making it a popular choice for travellers. The property has three bedrooms and one bathroom, comfortably accommodating up to six guests. It offers a fully equipped kitchen, a garden, free on-site laundry facilities, and pet-friendly accommodation for up to two dogs.
9.6 220 reviews
Sheboygan, WI
06/08 – 09/08
$611/nighttotal: $1833 (3 )
Spacious & Peaceful Home In The Heart Of Sheboygan
1 2
apartment , Sheboygan
This apartment is located in a peaceful neighbourhood just 800 metres from downtown Sheboygan, within a 15-minute drive of Kohler golf courses and Elkhart Lake. It has received excellent ratings for user experience, location, and cleanliness. The three-bedroom property can accommodate up to five guests and features a fully equipped kitchen, washer and dryer, comfortable living spaces, and a private parking space with a fenced-in backyard. Guests can enjoy easy access to restaurants, coffee shops, and nightlife in the city centre, as well as nearby attractions like Whistling Straits and Road America.
9.8 53 reviews
Sheboygan, WI
18/09 – 25/09
$289/nighttotal: $2023 (7 )
The Perfect Location!
3 4
apartment , Sheboygan
This three-bedroom apartment is located in Sheboygan, just a short walk from both the historic downtown area and the beach, offering easy access to shops, restaurants, and the lakeside. The apartment has consistently received excellent ratings for location, cleanliness, and overall user experience. The property offers a spacious living area with a fully equipped kitchen, dining room, and three bedrooms, comfortably accommodating up to six guests. Amenities include a private garden, a front patio, free street parking, Wi-Fi, a washer and dryer, and a small yard, providing plenty of space for relaxation and outdoor activities.
8.0 2 reviews
Sheboygan, WI
27/06 – 28/06
$543/nightfor 1 night
Apartment Near Many Locations.
4 5
apartment , Howards Grove
This Howards Grove apartment, a short distance (less than 1.6km) from Esch Library and Lakeland University, offers convenient access to both educational facilities and Lake Michigan (approximately 14.5km away). This four-bedroom, two-bathroom property sleeps seven guests and includes amenities such as a fully equipped kitchen, on-site laundry, and is within easy reach of the Rhine Center Bog State Natural Area (approximately 14.5km away).
10 5 reviews
Sheboygan, WI
20/09 – 25/09
$359/nighttotal: $1795 (5 )
Lake Breeze Cottage
Walk To Beach, Marina, Shops.
1 4
apartment , Sheboygan
Lake Breeze Cottage, a three-bedroom apartment in Sheboygan, is situated one block from Lake Michigan, offering easy access to the beach and Sheboygan's downtown area. This self-catering property sleeps six guests and includes a fully equipped kitchen with fridge, microwave, and dishwasher, plus air conditioning, parking, and internet access; enjoy swimming, sunbathing, or exploring nearby attractions.
Sheboygan, WI
26/07 – 30/07
$399/nighttotal: $1596 (4 )
The Parisian! – 2br Upper, Near Lake Michigan
1 4
apartment , Sheboygan
This two-bedroom, one-bathroom upper duplex in Sheboygan is located within a 1.2-kilometre walk of Lake Michigan and a short drive from downtown Sheboygan's dining, shopping, and beaches. This pet-friendly apartment, accommodating up to six guests, features a Parisian-inspired décor, air conditioning, a fully equipped kitchen with a dishwasher and microwave, and off-street parking.
Best family friendly Sheboygan, WI Short term rentals
Among the 219 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals
Sheboygan, WI
25/07 – 26/07
$316/nightfor 1 night
Apartment Centrally Located
2 3
apartment , Howards Grove
This flat is situated in Plymouth, just 3.2 kilometres from Road America and 32 kilometres from the beach, on the Lakeland University campus. Offering 114 square metres of living space for up to four guests, this apartment features two bedrooms, one bathroom, a full kitchen, a living room, a private patio, and access to shared laundry facilities, a grill, and nature trails, with free on-site parking.
10 3 reviews
Sheboygan, WI
26/07 – 30/07
$1359/nighttotal: $5436 (4 )
Central Located. Seconds From The Highway To Get To Kohler, And Elkhart Lake
4 4
apartment , Sheboygan
This four-bedroom house is located in Sheboygan, less than 2km from Lake Michigan and just under 1.5km from HSHS St. Nicholas Hospital. It has received excellent user ratings and is perfect for families or groups of up to 14 people. The property features a fully equipped kitchen with a fridge, microwave, dishwasher, and coffee maker, as well as a terrace, garden, and parking. Guests can enjoy amenities such as air conditioning, internet access, a washing machine, and a Smart TV.
9.9 83 reviews
Sheboygan, WI
20/09 – 25/09
$318/nighttotal: $1590 (5 )
Grammy’s House In A Quiet And Convenient Location
1 4
apartment , Sheboygan
This family-friendly four-bedroom house in central Sheboygan offers convenient access to local attractions and amenities. The property boasts a finished basement with office space, play area, and workout equipment, comfortably accommodating eight guests with a fully equipped kitchen and a newly enclosed toilet; a 10% discount is available for returning guests.
10 327 reviews
Sheboygan, WI
26/07 – 30/07
$679/nighttotal: $2716 (4 )
Remodeled Home On Lake Michigan
3 4
apartment , Sheboygan
This three-bedroom apartment is situated just south of Sheboygan's city centre, a short walk from restaurants, shops, and entertainment, and less than 1km from two public parks with beaches. The property has consistently received excellent ratings for location, cleanliness, and overall user experience. The apartment offers 135 square metres of space, comfortably accommodating up to seven guests. It features a fully equipped kitchen, a spacious living area, a private terrace, and a garden, providing a comfortable and relaxing stay.
Best Sheboygan, WI lodging with a balcony
10 12 reviews
Sheboygan, WI
10/08 – 13/08
$1290/nighttotal: $3870 (3 )
Beachside, Chefs Kitchen, High-end Everything
3 2
apartment , Sheboygan
This Sheboygan holiday home, located in the Ellis Historical District, offers easy walking access to Lake Michigan, the riverfront, and Sheboygan's downtown area, including its lighthouse. The 175-square-metre (1884 square foot) property boasts three bedrooms, three bathrooms, sleeping up to six guests, and features a modern open-plan design, a well-equipped kitchen, and outdoor amenities including a deck with a gas grill and access to beach fire rings; nearby attractions include the John Michael Kohler Arts Center and the Stefanie H. Weill Center for the Performing Arts.
This four-bedroom beachfront apartment in Sheboygan's city centre, situated within the Blue Harbor Resort on Lake Michigan, offers easy access to attractions such as the Stefanie H. Weill Center and John Michael Kohler Arts Center. The 186-square-metre property sleeps ten guests, features three bathrooms (including a master suite with jacuzzi), a fully equipped kitchen, and a private balcony overlooking the courtyard and lake; nearby amenities include the Blue Harbor Resort & Conference Center Water Park and Above & Beyond Children's Museum.
10 32 reviews
Sheboygan, WI
20/09 – 25/09
$484/nighttotal: $2420 (5 )
Beachside Condo W/ Stunning Lake Views
2 4
apartment , Sheboygan
This Sheboygan beachfront apartment, less than 1.6km from St Peter Claver Parish, Blue Harbor Resort & Conference Centre, and the John Michael Kohler Arts Centre, offers direct Lake Michigan access. The 74 square metre self-catering property features two bedrooms, one bathroom, sleeps five, and includes a fully equipped kitchen, private balcony, free Wi-Fi, and on-site garden and barbeque facilities.
10 8 reviews
Sheboygan, WI
06/08 – 09/08
$1418/nighttotal: $4254 (3 )
The Links! - Luxury Golf Retreat With Golf Simulator
4 2
apartment , Sheboygan
This four-bedroom Sheboygan dwelling is conveniently located near Blackwolf Run golf course and the Above & Beyond Children's Museum, with Deer Trace Mall and the Farmers Market also within easy reach. The self-catering property sleeps eight guests comfortably in two king and two queen beds across four bedrooms, three bathrooms, and boasts a terrace, parking, internet access, and a fully equipped kitchen including a fridge, microwave, and dishwasher.
Frequently Asked Questions about short term rentals in Sheboygan, WI
What attractions should you visit during a week-long stay in Sheboygan, Wisconsin?
A week in Sheboygan offers plenty to explore! Start with the Sheboygan Maritime Museum, showcasing the city's rich shipbuilding history. Then, head to the John Michael Kohler Arts Center, known for its impressive collection and rotating exhibits. A stroll along the Sheboygan Riverwalk is a must, offering beautiful views. Consider visiting the Blue Harbor Resort & Spa for some relaxation. For outdoor activities, explore the trails at Evergreen Park or Kohler-Andrae State Park. Don't forget to check out the local shops and boutiques in downtown Sheboygan.
What are the best short term rentals in Sheboygan, WI?
What attractions should you visit when you spend a month in Sheboygan, Wisconsin?
With a month, you can delve deeper into Sheboygan's offerings. Beyond the attractions mentioned for a week-long trip, explore the local breweries, such as 3 Sheeps Brewing Company and Sheboygan Brewing Company. Take day trips to nearby towns like Kohler, famous for its Kohler Company and golf courses. Visit the Wisconsin Cheese Mart for a taste of Wisconsin's dairy heritage. Spend time exploring the beaches along Lake Michigan, like those at Kohler-Andrae State Park. Consider attending a performance at the Weill Center for the Performing Arts. You could also explore the many parks and nature trails in the surrounding area, such as the Oostburg State Park.
What are the best short term rentals with a pool in Sheboygan, WI?
Can visitors to Sheboygan, Wisconsin witness any unique natural cycles, like cherry blossom season or autumn colors?
While Sheboygan doesn't have widespread cherry blossoms like some areas, the autumn colors in the parks and surrounding areas are quite stunning, typically peaking in October. Kohler-Andrae State Park and Evergreen Park are excellent spots for viewing the fall foliage.
What are the best short term rentals with a jacuzzi in Sheboygan, WI?
What are the most meaningful ways to engage with locals and discover the culture in Sheboygan, Wisconsin?
To connect with locals, visit the farmers' markets during the summer months, where you can interact with vendors and sample local produce. Attend events at the Weill Center for the Performing Arts or check out local festivals. Exploring the downtown area and chatting with shop owners is another great way to engage with the community. Consider visiting local restaurants and trying the unique dishes. Sheboygan has a strong German heritage, so exploring that aspect of the culture could be particularly rewarding.
What are the best short term rentals for families and kids in Sheboygan, WI?
Are there any distinctive cultural activities or hands-on workshops in Sheboygan, Wisconsin?
The John Michael Kohler Arts Center often hosts workshops and classes related to art and creativity. Check their website for current offerings. Many local breweries offer tours and tastings. You might also find pottery classes or other craft workshops at local studios, although availability varies.
What are some secret spots or hidden treasures to visit in Sheboygan, Wisconsin?
One relatively undiscovered gem is the Bookworm Gardens, a unique outdoor children's book-themed garden. Exploring the quieter residential streets near the lake can reveal charming architecture and hidden parks. The local beaches outside of the main areas can offer a more secluded experience. Look for smaller, family-owned shops and restaurants off the main streets for a more authentic Sheboygan experience.
What should not be left out of your suitcase if you are going to Sheboygan, Wisconsin?
Pack comfortable walking shoes, as you'll likely be doing a lot of exploring on foot. Layers are essential, as the weather can be unpredictable. Don't forget swimwear if you plan on visiting the beaches. Sunscreen and insect repellent are also recommended, especially during the warmer months.
What are the most popular festivals in Sheboygan, Wisconsin?
Sheboygan has several festivals throughout the year. The Brat Days festival is a popular event, celebrating bratwurst. The Wisconsin Cheese Festival (though not exclusively Sheboygan) often draws large crowds. There are also smaller, local events throughout the year, best checked through the local event listings closer to your travel dates.
Where should you try the best local food in Sheboygan, Wisconsin?
For a taste of Sheboygan's culinary scene, try restaurants like the 8th Street Ale Haus for pub fare and local brews. The Black Pig is known for its upscale dining experience. Many smaller eateries offer delicious and authentic Wisconsin cuisine. Don't forget to try some local cheese and bratwurst at various locations throughout the city.
Nearby regions
Best Sheboygan, WI lodging with a kitchen
10 1 review
Sheboygan, WI
25/07 – 26/07
$543/nightfor 1 night
Apartment Near Many Locations.
4 6
apartment , Howards Grove
This Plymouth apartment, situated less than 1.6km from Esch Library and Lakeland University and 14.5km from Lake Michigan, offers easy access to local amenities and attractions. Sleeping seven guests, this four-bedroom, two-bathroom dwelling boasts a fully equipped kitchen, including oven, hob, microwave and fridge, plus a washing machine and coffee/tea maker; nearby activities include exploring the Rhine Center Bog State Natural Area.
9.6 40 reviews
Sheboygan, WI
20/09 – 25/09
$386/nighttotal: $1930 (5 )
Coastal Comfort & Golfers' Paradise In Sheboygan!
3 4
apartment , Sheboygan
This holiday home is located in the Ellis Historical District of Sheboygan, less than 800 metres from Lake Michigan and a short walk to Deland Park. It has received excellent reviews from previous guests, making it a popular choice for travellers visiting the area. The property has three bedrooms and two bathrooms, spanning 93 square metres and comfortably accommodating up to six guests. The home offers a range of amenities including a fully equipped kitchen, a spa, air conditioning, free Wi-Fi, and parking, making it a perfect base for exploring the local area.
9.7 244 reviews
Sheboygan, WI
06/08 – 09/08
$833/nighttotal: $2499 (3 )
Serene Home One Block From Lake Michigan
3 2
apartment , Sheboygan
This apartment is located just a block from Lake Michigan and Deland Park in Sheboygan, within walking distance of North Beach and the YMCA, and minutes from the town centre. The property has excellent user, location, and cleanliness ratings, making it a great choice for travellers looking for a comfortable and convenient stay. The apartment is a two-storey property with three bedrooms, two bathrooms and can accommodate up to six guests. It has a fully equipped kitchen with a fridge, microwave and dishwasher, as well as air conditioning and parking. Guests can enjoy relaxing by the lake or exploring the nearby golf courses, shops, and restaurants.
9.9 52 reviews
Sheboygan, WI
10/08 – 13/08
$237/nighttotal: $711 (3 )
Peaceful Apartment Close To The Lake
1 2
apartment , Sheboygan
This centrally located Sheboygan apartment offers easy walking access to downtown Sheboygan's restaurants, bars, parks, beach, and the Stephanie H. Weill Center for the Performing Arts. The two-bedroom, one-bathroom flat sleeps four guests, features a fully equipped kitchen with dishwasher, in-unit laundry, a private balcony, high-speed internet, and smart TVs; nearby attractions include Kohler's golf courses, roughly 10-15 minutes' drive away.
Best Sheboygan, WI lodging with laundry available
9.8 21 reviews
Sheboygan, WI
18/09 – 25/09
$263/nighttotal: $1841 (7 )
Sheboygan Sunrise Beach Stay
1 4
apartment , Sheboygan
This Sheboygan apartment, a first-floor condo centrally located in Sheboygan, offers easy walking access to Lake Michigan, the beach, and attractions such as the Riverwalk, South Pier District, and Fish Shanty Village. The two-bedroom, one-bathroom flat sleeps up to six guests, featuring a fully equipped kitchen, keyless entry, ample street parking, and a cosy living area with a fireplace and pull-out sofa bed; nearby activities include visiting the John Michael Kohler Arts Centre.
10 4 reviews
Sheboygan, WI
06/08 – 09/08
$1208/nighttotal: $3624 (3 )
Riverfront Condo Steps To Downtown & Lake Michigan
3 2
apartment , Sheboygan
This riverfront flat in Sheboygan's South Pier District offers a peaceful escape, just 300 meters from downtown's shops and restaurants, and a short walk to Southside Beach and the Lake Michigan pier. This spacious 3-bedroom, 2-bathroom condo accommodates up to six guests, featuring a fully equipped kitchen, a living room with a fireplace, air conditioning, a private balcony with water views, and allowing pets.
9.8 35 reviews
Sheboygan, WI
10/08 – 13/08
$490/nighttotal: $1470 (3 )
4 Bedroom Home On The River With Private River Access
4 2
apartment , Sheboygan
This Sheboygan waterfront holiday home offers private river access with kayaks and is conveniently located near Lake Michigan and Kohler-Andrae State Park, distances to specific attractions unspecified. The 149 square metre (1600 square feet) property boasts four bedrooms, two bathrooms, sleeps eight guests, and includes a fully equipped eat-in kitchen, family room with smart TV and board games, and a serene backyard oasis with a fireplace.
9.4 140 reviews
Sheboygan, WI
26/07 – 30/07
$219/nighttotal: $876 (4 )
Vintage Sheboygan
1 4
apartment , Sheboygan
This three-bedroom apartment in Sheboygan is located just 1.6 kilometres from the Lake Michigan beach and within walking distance of the 8th Street restaurants. The apartment features a spacious living room, an eat-in kitchen with a separate butler's pantry, and a bathroom with a clawfoot tub shower enclosure, offering ample space for a comfortable stay.
