Find short term rentals in Sheboygan, WI at the best prices
219 available short term rental offers
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Accommodation type
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Best Short term and Weekly rentals in Sheboygan, WI
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.
9.8 35 reviews
Sheboygan, WI
02/07 – 05/07
$2305/nighttotal: $6915 (3 )
6 Bedroom House On 7 Acres
6 6
apartment , Sheboygan Falls
This Sheboygan Falls holiday home is situated 0.8km from The Bull at Pinehurst Farms Golf Course and 2.3km from Evans, with Deer Trace Mall and the Kohler Design Center within a 9.6km radius. This nine-bedroom, four-bathroom property sleeps eighteen guests and boasts a fully equipped kitchen, Jacuzzi, fitness centre, and parking, offering a smoke-free environment with added amenities like a washing machine and fireplace.
10 1 review
Sheboygan, WI
27/06 – 28/06
$543/nightfor 1 night
Apartment Near Many Locations.
4 5
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.
10 36 reviews
Sheboygan, WI
18/09 – 25/09
$356/nighttotal: $2492 (7 )
Family Cottage, Walk To The Lake (Pet Friendly)
1 4
apartment , Sheboygan
This Sheboygan holiday home is situated on the North Side, 0.24km from Lake Michigan and 1.6km from North Side Municipal Beach. The three-bedroom, 1.5-bathroom property sleeps six, features a fully equipped kitchen including a dishwasher, and offers Wi-Fi, air conditioning, and on-site parking.
10 8 reviews
Sheboygan, WI
02/07 – 05/07
$1290/nighttotal: $3870 (3 )
The Links! - Luxury Golf Retreat With Golf Simulator
4 6
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.
10 4 reviews
Sheboygan, WI
06/08 – 09/08
$534/nighttotal: $1602 (3 )
Overlook Oasis - Coastal Haven In Ellis District
3 2
apartment , Sheboygan
This Sheboygan apartment, located in the Ellis District, is steps from the lakefront walk, Blast Ice Cream, and Harbor Lights Bar, and a short walk from DeLand Park. The newly remodelled, three-bedroom flat sleeps six guests, offering two queen beds and a king trundle, a fully equipped kitchen with stainless steel appliances, high-speed Wi-Fi, and free on-street parking; nearby attractions include Kohler-Andrae State Park and the John Michael Kohler Arts Center.
Sheboygan, WI
03/07 – 06/07
$479/nighttotal: $1437 (3 )
The Beach Town Bungalow
2 2
apartment , Sheboygan
This two-bedroom flat in Sheboygan is a 10-minute walk from the Sheboygan County Historical Museum and a 5-minute drive from Lake Michigan. This apartment accommodates up to five guests and features air conditioning, a garden, a balcony, and on-site parking, with a fully equipped kitchen including a fridge and microwave oven, and in-unit internet access.
10 2 reviews
Sheboygan, WI
03/07 – 06/07
$1848/nighttotal: $5544 (3 )
Walk To Beach & Pier | Fully-loaded Kitchen
5 2
apartment , Sheboygan
This Sheboygan city centre holiday let offers proximity to Lake Michigan's public beach and the North Pier, with Kohler golf courses and Road America a short drive away. This spacious 5-bedroom, 4-bathroom holiday house accommodates up to 11 guests, featuring a fully equipped kitchen, air conditioning, dedicated office space, and is conveniently located near dining, shopping, and family attractions.
9.9 24 reviews
Sheboygan, WI
03/07 – 06/07
$182/nighttotal: $546 (3 )
Private Guest Bedroom - 2e East Room - Close To Lake Michigan
1 2
B&B , Sheboygan
This charming bed and breakfast is located in a quiet residential area of Sheboygan, just 3 kilometres from the Children's Museum and within easy reach of Lake Michigan. It has consistently received excellent ratings for its cleanliness, location, and overall guest experience. The property features a comfortable bedroom, two bathrooms, and a fully equipped kitchen, offering a total floor area of 9 square metres and accommodating up to two guests. Enjoy the peaceful courtyard views, relax in the Jacuzzi, and make the most of the outdoor fireplace, the tennis court, and the rental services for bicycles and cars.
9.9 119 reviews
Sheboygan, WI
18/09 – 25/09
$295/nighttotal: $2065 (7 )
Spacious/stylish, 2br Loft
2 4
apartment , Sheboygan
This apartment is situated in a walkable neighbourhood in Sheboygan, just a short distance from shops, restaurants, museums, and the lakefront. It has consistently received excellent ratings for its cleanliness, location, and overall experience. This two-bedroom, one-bathroom home can comfortably accommodate up to six guests. It features a well-equipped kitchen, in-unit laundry, smart TVs, free Wi-Fi, and convenient parking.
10 1 review
Sheboygan, WI
26/07 – 30/07
$339/nighttotal: $1356 (4 )
Fresh Coast Craftsman - Pet Friendly | Near Lake
1 4
apartment , Sheboygan
This two-bedroom flat is located in a residential district of Sheboygan, offering convenient access to city amenities and the Great Lakes, approximately 5 kilometres away. This pet-friendly residence accommodates up to four guests and includes a secure two-car garage, on-site laundry facilities, a smart TV, and a fully fenced garden, making it ideal for families or groups seeking a comfortable stay with all necessary conveniences.
9.9 155 reviews
Sheboygan, WI
20/09 – 25/09
$200/nighttotal: $1000 (5 )
King Bed Near Lake W/ Fire Pit & Pack N Play
1 4
apartment , Sheboygan
This three-bedroom lower duplex is located near Lake Michigan, Whistling Straits golf course, and Kohler-Andrae State Park in Sheboygan, offering easy access to these attractions. Sleeping up to five guests, this self-catering property boasts a fully equipped kitchen, private backyard with fire pit, smart TV, and complimentary amenities including coffee, popcorn, and essential toiletries; board games and puzzles are also provided for indoor entertainment.
Best family friendly Sheboygan, WI Short term rentals
Among the 219 accommodations in Sheboygan, WI, here are the 4 best family friendly rentals
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.
10 65 reviews
Sheboygan, WI
20/09 – 25/09
$174/nighttotal: $870 (5 )
A Wave From It All! - Lake Condo
1 4
apartment , Sheboygan
This ground floor apartment is conveniently located just a short walk, less than 1.6km, from the South Boardwalk and North Beach in Sheboygan, offering easy access to the city's attractions and scenic lakefront views. The apartment consistently receives excellent ratings for its location, cleanliness, and overall experience, making it a popular choice for travellers. The apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a comfortable living area, and a keyless entry system. Guests can enjoy amenities such as a smart TV, free Wi-Fi, and a relaxing electric fireplace, while exploring the nearby historical sites and enjoying the beautiful lakefront views.
9.8 52 reviews
Sheboygan, WI
10/08 – 13/08
$1030/nighttotal: $3090 (3 )
Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub
1 2
apartment , Sheboygan
Sheboygan Chalet, a four-bedroom lodge in Sheboygan's Black River neighbourhood, is situated two blocks from Lake Michigan and a short walk from Majerle's Supper Club, ten minutes' drive from Sheboygan's town centre. This self-catering holiday home sleeps up to 13 guests and boasts a chef's kitchen, games room with PS5 and arcade machines, hot tub, infrared sauna, and two expansive decks, all within easy reach of the beach and marina.
10 143 reviews
Sheboygan, WI
20/09 – 25/09
$198/nighttotal: $990 (5 )
House Near The Lake
2 4
apartment , Sheboygan
This family home is located one block from Lake Michigan in Sheboygan, Wisconsin, offering easy access to three parks, two beaches, and is within a 16km drive of Terry Andrae State Park. The two-bedroom, one-bathroom property sleeps four, boasts a fully equipped kitchen including fridge, freezer and microwave, air conditioning, a garden, parking, and excellent guest reviews; nearby attractions include the Kohler Art Center and Road America, approximately 48km away.
Best Sheboygan, WI lodging with a balcony
9.6 12 reviews
Sheboygan, WI
20/09 – 25/09
$493/nighttotal: $2465 (5 )
Sheboygan Getaway W/ Deck + On-site Lake Access!
2 4
apartment , Sheboygan
This apartment is situated in Sheboygan, just 3.2 kilometres from the city centre and less than 1.6 kilometres from South Shore Beach, offering a peaceful retreat close to the city's attractions. The property has received excellent reviews from previous guests, highlighting its comfortable and convenient location. This two-bedroom flat, spanning 93 square metres, comfortably accommodates up to five guests, making it ideal for families or groups. The apartment provides a fully equipped kitchen, a private balcony, and access to a range of amenities, including a washing machine and dryer, plus the added benefit of lake views and on-site parking.
Sheboygan, WI
18/09 – 25/09
$477/nighttotal: $3339 (7 )
At River's Edge - Charming 2br River Retreat With Garage
2 4
apartment , Sheboygan
This waterfront flat in Sheboygan, located on the Sheboygan River, offers serene views and is within minutes of Lake Michigan, downtown dining, and local attractions such as Deland Park. This two-bedroom flat accommodates up to six guests and features a king suite with a private balcony, a second bedroom with two queen beds, in-unit laundry, and an attached two-car garage, with the Sheboygan Riverwalk just a short walk away.
This spacious apartment is located in Sheboygan, just 5 kilometres from the Whistling Straits Golf Course and close to Kohler Spa, beautiful parks, and beaches. It has an excellent user rating, making it a popular choice for travellers. The property has 5 bedrooms and 4 bathrooms, comfortably accommodating up to 14 guests. Amenities include a golf simulator/theatre room, a Zen Den, a poker room, a garden, a terrace, a jacuzzi, air conditioning, a fully equipped kitchen, and internet access.
9.6 7 reviews
Sheboygan, WI
04/07 – 06/07
$378/nighttotal: $756 (2 )
The Historic Downtown Suite
2 2
apartment , Sheboygan Falls
This Historic Downtown Suite in Sheboygan Falls offers a convenient location close to local shops and restaurants, and is 10km from the Children's Museum. The 74 square metre apartment features two bedrooms, one bathroom, and sleeps up to ten guests, boasting a fully equipped kitchen, private balcony, free Wi-Fi, and free private parking.
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 20 reviews
Sheboygan, WI
26/07 – 30/07
$1207/nighttotal: $4828 (4 )
Luxury 4b-2ba Lake & Beach House
1 4
apartment , Sheboygan
This luxurious Sheboygan lakeside property is situated just 0.16 kilometers from Lake Michigan, offering breathtaking lake views and easy access to Sheboygan's attractions. This four-bedroom, two-bathroom house sleeps eight, boasts a fully equipped kitchen including dishwasher, air conditioning, parking, and enjoys a prime location for exploring the city.
9.9 42 reviews
Sheboygan, WI
06/08 – 09/08
$440/nighttotal: $1320 (3 )
Newly Updated! Downtown & Shore
1 2
apartment , Sheboygan
This apartment in Sheboygan is conveniently located just 4 kilometres from the city centre and 5 kilometres from the lakeshore, offering easy access to restaurants, shops, and beaches. The property has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment is spacious and can accommodate up to 6 guests, with comfortable queen-sized beds in each bedroom. Guests can enjoy a fully equipped kitchen, free laundry facilities, and peaceful nights with blackout shades and white noise machines.
10 58 reviews
Sheboygan, WI
06/08 – 09/08
$342/nighttotal: $1026 (3 )
The Sheboygan Foodie Flat
1 2
apartment , Sheboygan
This newly renovated Sheboygan flat, situated in the Eastside district, is within walking distance of Lake Michigan's beaches, the riverfront, and the Uptown/Downtown areas. The self-contained apartment, sleeping two guests, boasts a queen-sized bed, a well-equipped kitchenette with a convection oven and microwave, a spacious bathroom with a walk-in shower, and access to a shared patio and garden.
9.9 93 reviews
Sheboygan, WI
20/09 – 25/09
$228/nighttotal: $1140 (5 )
Quaint Blast From The Past - Walk To Lake/8th St
1 4
apartment , Sheboygan
This renovated two-bedroom apartment is situated in Sheboygan's historic downtown district, within walking distance of Lake Michigan and its scenic trails. The 111.5 square metre (1200 sq ft) property sleeps six, offering a spacious layout, a media centre with record player, and is pet-friendly (non-shedding dogs only, extra fee applies).
Best Sheboygan, WI lodging with laundry available
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.
9.9 116 reviews
Sheboygan, WI
26/07 – 30/07
$542/nighttotal: $2168 (4 )
Janelle's Dockside Condo
1 4
apartment , Sheboygan
This two-bedroom apartment is located in Sheboygan's South Pier District, just a short walk from the boardwalk and its attractions, offering easy access to the area's charm and attractions. It has received excellent ratings for location, cleanliness, and overall guest experience. The property has two bathrooms and can accommodate up to four guests. The apartment comes equipped with modern amenities, including a fully equipped kitchen, air conditioning, and a private deck overlooking Lake Michigan. Guests can enjoy the nautical theme, explore the nearby golf courses, or simply relax and take in the scenic views.
9.9 182 reviews
Sheboygan, WI
20/09 – 25/09
$190/nighttotal: $950 (5 )
Lux Downtown Escape | Outdoor Movie Screen
1 4
apartment , Sheboygan
This historic 1885 house in downtown Sheboygan offers a prime location, within a short walk (less than 0.8 km) of Lake Michigan beaches, restaurants, and theatres. The two-bedroom, one-bathroom property sleeps four guests and features a fully equipped chef's kitchen, a private garden with a barbecue and outdoor cinema screen, and parking; the entire house (excluding basement and utility areas) is available for guest use.
10 15 reviews
Sheboygan, WI
18/09 – 25/09
$214/nighttotal: $1498 (7 )
Quaint Blast From The Past - Walk To Lake Michigan, Riverwalk And 8th St Shops!
2 4
apartment , Sheboygan
This Downtown Sheboygan apartment is situated less than 1.6km from Lake Michigan, the John Michael Kohler Arts Centre, and the Blue Harbor Resort & Conference Centre water park. This 102 square metre, two-bedroom, one-bathroom flat sleeps six guests and boasts a fully equipped kitchen, private balcony, swimming pool, spa, parking, and free Wi-Fi.
