Search cheap accommodations in Sheboygan, WI from 100+ sites!

419 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Sheboygan, WI accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

419 Lodgings in Sheboygan, WI

Best Sheboygan, WI lodging with a pool

Among the 419 accommodations in Sheboygan, WI, here are the 2 best ones with a pool

Baronwood Oasis | Pool + Arcade Mega Estate - Sheboygan, WI
10 9 reviews

Baronwood Oasis | Pool + Arcade Mega Estate

apartment, Sheboygan
This 10,500-square-foot luxury estate in Sheboygan, Wisconsin, is minutes from the Whistling Straits golf course, Kohler Co. amenities, and Lake Michigan.
This seven-bedroom, seven-bathroom home sleeps twenty guests and boasts an indoor pool and spa, a private arcade, a gourmet chef's kitchen, and concierge services including private chefs and massage therapists.
Blue Harbor Resort And Conference Center - Sheboygan, WI
8.4 523 reviews

Blue Harbor Resort And Conference Center

resort, Sheboygan
Blue Harbor Resort and Conference Center sits right on the Sheboygan beach, just a short walk from the John Michael Kohler Arts Center, Stefanie H. Weill Center for the Performing Arts, and Above & Beyond Children's Museum. This resort consistently receives very good ratings from previous guests.
The resort offers a variety of accommodations for couples and families. Guests can enjoy a full-service spa, a complimentary waterpark, a fitness center, a restaurant, a bar, and a garden.

Best family friendly Sheboygan, WI lodging

Among the 419 accommodations in Sheboygan, WI, here are the 4 best for families

Clean, Comfy Stay Near Parks, Downtown & Lake! - Sheboygan, WI
10 56 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

apartment, Sheboygan
This Sheboygan apartment rental is conveniently located near Interstate 43, directly across from Shaw Family Park, and within walking distance of a Starbucks.
The two-bedroom, one-bathroom unit sleeps four guests and features a kitchen, air conditioning, parking, internet access, and proximity to Sheboygan's beachfront, Fireman's Park, and renowned golf courses like Whistling Straits.
Sleeps 7{spacious}pets Welcome! - Sheboygan, WI
9.4 3 reviews

Sleeps 7{spacious}pets Welcome!

apartment, Sheboygan
This Sheboygan lakeside rental is conveniently located 1.1 miles from HSHS St. Nicholas Hospital and 1.5 miles from Lake Michigan, also near the Sheboygan County Historical Museum and Above & Beyond Children's Museum.
This three-bedroom, one-bathroom apartment sleeps seven, features a fully equipped kitchen, in-unit laundry, free WiFi, a Smart TV, and a garden, offering a smoke-free and pet-friendly environment.
The Garden | Sheboygan 2 Br/1ba, Pet Friendly - Sheboygan, WI
9.7 103 reviews

The Garden | Sheboygan 2 Br/1ba, Pet Friendly

apartment, Sheboygan
The Garden apartment is located in downtown Sheboygan, just three blocks from Lake Michigan, offering easy access to the city's attractions and the beautiful lakefront. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience. The apartment features two bedrooms and one bathroom, comfortably accommodating up to four guests. The well-equipped kitchen includes a fridge, freezer, microwave oven, and dishwasher, while amenities like air conditioning, parking, internet, and pet-friendly policies ensure a comfortable and convenient stay.
Logan Ave Holiday House - Upper - Sheboygan, WI
9.8 6 reviews

Logan Ave Holiday House - Upper

apartment, Sheboygan
This apartment in Sheboygan is a short walk from Lake Michigan and downtown, offering convenient access to local attractions such as the Stefanie H. Weill Center for the Performing Arts, John Michael Kohler Arts Center, and Above & Beyond Children's Museum. It has a very good user rating.
The apartment features 2 bedrooms and 1 bath, providing ample space for up to 6 guests. It has a floor area of 1000 square feet and includes modern amenities such as a fridge, microwave oven, dishwasher, air conditioning, and internet. Guests can also enjoy the outdoor amenities, including a lovely backyard, and access to nearby cross-country skiing and sledding opportunities. Ample parking is available for guests, and pets are welcome.

Frequently Asked Questions about accommodations in Sheboygan, WI

  • What are the must-see attractions in Sheboygan, Wisconsin?

    Sheboygan has a lot to offer! The Sheboygan Maritime Museum is a great place to learn about the city's rich history as a shipbuilding and fishing center. The John Michael Kohler Arts Center showcases contemporary art in a beautiful setting. For a taste of local history and architecture, a stroll through the downtown area is a must. And don't forget the beautiful Sheboygan Riverwalk, perfect for a relaxing walk or bike ride.
  • What are the best accommodations in Sheboygan, WI?

    Among the accommodations in Sheboygan, WI, Grandstay Hotel & Suites Downtown Sheboygan, Americinn By Wyndham Sheboygan and La Quinta Inn By Wyndham Sheboygan are the most popular ones.

  • Are there any seasonal events or cultural festivals in Sheboygan, Wisconsin?

    Sheboygan hosts several events throughout the year. The Brat Days festival is a huge celebration of, you guessed it, brats! It typically takes place in the summer. The city also hosts various smaller events throughout the year, so checking the local event calendar closer to your travel dates is advisable.
  • What are the best accommodations with a pool in Sheboygan, WI?

    Grandstay Hotel & Suites Downtown Sheboygan, Americinn By Wyndham Sheboygan and Harbor Winds Hotel are the best accommodations with a pool in Sheboygan, WI.

  • What are the most characteristic landscapes and terrains found in and around Sheboygan, Wisconsin?

    Sheboygan sits on the shores of Lake Michigan, so the lakefront is a dominant feature, offering beautiful beaches and views. The terrain is relatively flat, typical of the Wisconsin landscape, with rolling hills and farmland surrounding the city. The Sheboygan River winds its way through the city, adding to the scenic beauty.
  • What are the best accommodations with a jacuzzi in Sheboygan, WI?

  • What are the best outdoor activities in Sheboygan, Wisconsin?

    Sheboygan offers many outdoor activities. The lakefront provides opportunities for swimming, sunbathing, and walking or biking along the paved paths. The Sheboygan Riverwalk is ideal for leisurely strolls or cycling. Several parks in and around the city offer opportunities for picnics, hiking, and other recreational pursuits. The area is also great for fishing.
  • What are the best accommodations for families and kids in Sheboygan, WI?

  • What is the best time of year to visit Sheboygan, Wisconsin with kids?

    Summer is generally the best time to visit Sheboygan with kids, as the weather is warm and sunny, perfect for enjoying the beaches and outdoor activities. Brat Days, usually in summer, offers family-friendly fun.
  • What are the best pet friendly accommodations in Sheboygan, WI?

    The best pet friendly accommodations in Sheboygan, WI are Grandstay Hotel & Suites Downtown Sheboygan, La Quinta Inn By Wyndham Sheboygan and Harbor Winds Hotel.

  • Are there local customs to be aware of in Sheboygan, Wisconsin?

    Sheboygan is a friendly and welcoming city. There aren't any unusual or unique customs to be particularly aware of. Being respectful and polite, as you would anywhere, is always appreciated.
  • What are the best accommodations with parking in Sheboygan, WI?

  • What are the best ways to interact with locals and learn about their culture in Sheboygan, Wisconsin?

    Striking up conversations with people at local businesses, restaurants, or during community events is a great way to interact with locals. Visiting the Sheboygan County Historical Museum can also provide insights into the area's history and culture.
  • What are some lesser-known attractions or hidden gems in and around Sheboygan, Wisconsin?

    The Evergreen Cemetery, while perhaps not a typical tourist destination, offers a glimpse into the city's past with its beautiful architecture and historical markers. Exploring the smaller parks and neighborhoods can also unearth charming hidden gems. Checking local blogs or publications for lesser-known attractions could yield more discoveries.
  • What are some must-try local dishes in Sheboygan, Wisconsin?

    Sheboygan is known for its delicious brats, of course! Many restaurants offer unique variations. Local seafood is also a must-try, reflecting the city's proximity to Lake Michigan. Several restaurants offer creative dishes featuring fresh, locally sourced ingredients.

Nearby regions

Best Sheboygan, WI accommodation with a balcony

Fairway Getaway-by Whistling Straits, Golf Sim/theater Room, Zenden &Poker Room! - Sheboygan, WI
10 8 reviews

Fairway Getaway-by Whistling Straits, Golf Sim/theater Room, Zenden &Poker Room!

apartment, Sheboygan
This Sheboygan apartment is conveniently located just 5 minutes from Whistling Straits Golf Course and close to Kohler Spa, parks, and beaches. It has received excellent user ratings and is a great choice for families and groups visiting the area. The home sleeps up to 14 guests in its 5 bedrooms and 4 bathrooms. Amenities include a golf simulator/theater room, a poker room, a Zen den, a jacuzzi, a terrace, a garden, and a fully equipped kitchen.
Home Overlooking Lake Michigan - Sheboygan, WI
9.8 332 reviews

Home Overlooking Lake Michigan

apartment, Sheboygan
This Sheboygan apartment is located on a bluff overlooking Lake Michigan, just a short distance from downtown and two public beaches. The apartment consistently receives excellent ratings for its cleanliness, location, and overall experience.
The 1450 square foot apartment comfortably accommodates up to 7 guests with 3 bedrooms. Enjoy a modern, remodeled kitchen and bathrooms, a private terrace, a garden, and a spa, along with other amenities such as WiFi, parking, and air conditioning.
Quaint Blast From The Past - Walk To Lake Michigan, Riverwalk And 8th St Shops! - Sheboygan, WI
10 23 reviews

Quaint Blast From The Past - Walk To Lake Michigan, Riverwalk And 8th St Shops!

apartment, Sheboygan
This downtown Sheboygan rental is less than a mile from Lake Michigan, the John Michael Kohler Arts Center, and the Blue Harbor Resort water park.
The 1100-square-foot apartment features two bedrooms, one bathroom, sleeps six, and includes a fully equipped kitchen, free WiFi, a private balcony, a swimming pool, and a spa.
Beachside Beautifully Renovated Historic Home - Sheboygan, WI
No reviews

Beachside Beautifully Renovated Historic Home

apartment, Sheboygan
This newly renovated historic home in Sheboygan's Ellis Historical District offers an unparalleled waterfront location directly across from Deland Park and Lake Michigan, with downtown restaurants and shopping 4 blocks away.
This 3-bedroom, 2-bathroom rental accommodates up to 6 guests and features a full kitchen with a fridge, microwave, and dishwasher, air conditioning, multiple porches, and is a 15-minute drive from Whistling Straits.

Neighborhoods and points of interest in Sheboygan, WI

Best Sheboygan, WI accommodation with a kitchen

Recombobulation Station-in The Heart Of Sheboygan! - Sheboygan, WI
10 98 reviews

Recombobulation Station-in The Heart Of Sheboygan!

apartment, Sheboygan
This upper unit apartment is located just a few blocks from Sheboygan's North Beach and downtown 8th Street district, placing you within walking distance of restaurants, shops, and the beach. This vacation rental has received excellent ratings for its location, cleanliness, and user experience.
The apartment has two bedrooms and one bathroom, accommodating up to five guests. Enjoy modern amenities like air conditioning, a fully equipped kitchen, a washer/dryer, and a garden, making your stay comfortable and convenient.
Welcome To Harbor Nights! - Sheboygan, WI
9.3 29 reviews

Welcome To Harbor Nights!

apartment, Sheboygan
This three-bedroom Sheboygan apartment boasts a prime downtown location across from Blue Harbor Resort and within walking distance of South Pier.
The 3-bedroom rental features an eat-in kitchen with a full-sized refrigerator, stove, dishwasher, and microwave, in-unit laundry, and sleeps eight guests, offering stunning Lake Michigan and Sheboygan River views from its spacious layout.
Robin's Den Spacious 3brm King - Sheboygan, WI
9.6 54 reviews

Robin's Den Spacious 3brm King

apartment, Sheboygan
This Sheboygan apartment is located in the downtown area, within walking distance of the lakefront, shops, and restaurants. The apartment occupies the entire first floor of a Victorian-style house, creating a charming and unique ambiance.
The apartment comfortably accommodates up to seven guests with three king-sized beds and a designated workspace. This apartment offers modern amenities such as a full kitchen, in-unit washer and dryer, free Wi-Fi, four Roku TVs, and off-street parking.
Moonrise Kingdom Beach Shack. One Block To Beach. - Sheboygan, WI
9.9 88 reviews

Moonrise Kingdom Beach Shack. One Block To Beach.

house, Sheboygan
This Sheboygan carriage house, located one block from excellent surfing and two blocks from restaurants and a coffee shop, offers a prime location near the city's best waves. This one-bedroom, one-bathroom rental comfortably sleeps two guests, features a fully updated kitchen, on-site fitness equipment, a private garden, and convenient on-street parking.
©2026 cozycozy.com