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Sheboygan Holiday Rentals

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Holiday Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, 811 reviews
"Staff was great very accommodating "
The price is AU$291
per night
16 June - 17 June
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
9.8 out of 10, Exceptional, 217 reviews
"Very nice kitchen and living room. Small TV. Both bedrooms are on second floor with bath/shower on main living area. Lots of stairs, so if you have bad knees this place isn't for you. But the sunrises were amazing and it was quiet and so pleasant to sit out on the back deck on a cliff over looking Lake Michigan. Great location in Sheboygan."
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
REMODELED HOME ON LAKE MICHIGAN
10.0 out of 10, Exceptional, 142 reviews
"Great location and view of the lake. The kitchen is one of the best stocked I have seen in a while. Good layout for hanging out. Communication was easy."
REMODELED HOME ON LAKE MICHIGAN
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Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
10.0 out of 10, Exceptional, 3 reviews
"Very clean property, comfortable beds, and plenty to do for kids and adults alike."
The price is AU$640
per night
12 June - 13 June
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, 12 reviews
"Would highly recommend! It was very clean and newly remodeled. Had everything we needed and we felt right at home!"
The price is AU$570
per night
10 June - 11 June
*NEW* Sleeps 8 & Spacious!
Family-Friendly House: Walk to Lake Michigan!
9.4 out of 10, Exceptional, 3 reviews
"My family and I were in town for Christmas, and the house served as a great spot of us to hang our hats. Mike was a tremendous host who was very quick to respond to any questions. He even ensured that the house was pleasantly decorated for the season. The house is conveniently situated between town (~3 blocks) and the lake Michigan beaches (~2 blocks). We found the kitchen to be fully equipped and included a selection of K-cups for us to enjoy each morning. Most importantly, the house was clean...
Family-Friendly House: Walk to Lake Michigan!
3 Bedroom Beach House
10.0 out of 10, Exceptional, 6 reviews
"The owner was super amazing helping us reschedule our trip. The house was clean and the beds and pillows were very comfortable. I looked up what they were to order them :) Lots of food and bars close enough to walk to. Very close to the lake too."
3 Bedroom Beach House
Edgewater Escapes - 4 bed condo steps to the lake
9.2 out of 10, Wonderful, 9 reviews
"Place was great! Awesome location and lots of room."
The price is AU$1,525
per night
12 June - 13 June
Edgewater Escapes - 4 bed condo steps to the lake
Perfect Paradise : Luxury Beachfront Condo!
10.0 out of 10, Exceptional, 2 reviews
"The property was excellent. Clean and comfortable. Great location with close proximity to Blackwolf Run and Whistling Straits. Enjoyed our time at the property. Will rent again next year."
Perfect Paradise : Luxury Beachfront Condo!
Beach front luxury spacious villa !
10.0 out of 10, Exceptional, 31 reviews
"Very nice place. Much appreciated."
Beach front luxury spacious villa !
Cozy 2 bd home, minutes from lake Michigan
7.4 out of 10, Good, 11 reviews
"Cute place, very clean. Communication has been great, everything from check in through the stay has been easy and smooth!"
The price is AU$423
per night
14 June - 15 June
Cozy 2 bd home, minutes from lake Michigan
Walk to beach, restaurants, shops! Historic charm with updated amenities
10.0 out of 10, Exceptional, 44 reviews
"Carefully renovated home with charm and amenities for a lovely stay. Great location in quiet residental neighborhood close to the Lake and all that Sheboygan has to offer."
Walk to beach, restaurants, shops! Historic charm with updated amenities
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
10.0 out of 10, Exceptional, 157 reviews
"The property is clean, nice, and very welcoming. We enjoyed our stay from the moment we got on property. Highly recommend this property as we will be staying here next time in town!"
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
9.8 out of 10, Exceptional, 68 reviews
"Beautiful, comfortable, well stocked condo (towels, paper products, etc.). Exceptionally clean. Enjoyed our stay."
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
10.0 out of 10, Exceptional, 1 review
"Shawn has created an ideal getaway and we all highly recommend staying here. Everything was brand new and very clean. We had so much fun staying here for our friend's 40th birthday. There were 10 adults and we all had a comfortable place to sleep. The space is perfect for large groups and you could throw an amazing party. I would love to return in warmer weather and enjoy more time on the deck and front patio. There are spacious gathering areas and small quiet areas for when you need a little...
Fairway Getaway-by Whistling Straits, Golf sim/Theater Room, ZenDen &Poker Room!
Sheboygan Getaway w/ Deck + On-Site Lake Access!
10.0 out of 10, Exceptional, 1 review
"I felt is was exactly what i expected as per viewing pictures and description. Deck was an extra fun thing to be able to see Lake Michigan and watch the sunrise, we will be back !"
Sheboygan Getaway w/ Deck + On-Site Lake Access!
Shoreline Sanctuary - a Lakefront Retreat!
Shoreline Sanctuary - a Lakefront Retreat!
BEACHSIDE GETAWAY IN SHEBOYAN
10.0 out of 10, Exceptional, 10 reviews
"Well equipped and comfortable for a full week’s stay. Loved access to the beach for sunrise walks."
BEACHSIDE GETAWAY IN SHEBOYAN
4 Bedroom Beachfront Condo
10.0 out of 10, Exceptional, 47 reviews
"Very nice"
4 Bedroom Beachfront Condo
Lovely Lake Lookout - Beachfront Condo mins to Lake Michigan!
9.6 out of 10, Exceptional, 4 reviews
"The home was clean and has plenty of room to sleep a lot of people. It is only about 2 blocks from the beach and some shops. They thought of everything including floss and a makeup remover in each bathroom. The kitchen is well stocked with all that we needed."
Lovely Lake Lookout - Beachfront Condo mins to Lake Michigan!
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Sheboygan you may be interested in

La Quinta Inn by Wyndham Sheboygan
2.5 star property
8.0 out of 10, Very good, 1,007 reviews
"I was in town for the Golf Tournament and stayed an extra day. The area is beautiful and my stay was nice and quiet."
The price is AU$154
per night
16 June - 17 June
La Quinta Inn by Wyndham Sheboygan
Blue Harbor Resort and Conference Center
3.0 star property
8.4 out of 10, Very good, 414 reviews
"Nice property in a beautiful location. Nice amenities. "
Blue Harbor Resort and Conference Center
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, 811 reviews
"Staff was great very accommodating "
The price is AU$291
per night
16 June - 17 June
Grandstay Residential Suites Hotel - Sheboygan
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Sheboygan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheboygan holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sheboygan holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheboygan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheboygan holiday rentals we have selected for you start as low as AU$291 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheboygan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheboygan holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheboygan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Sheboygan speak positively about the popular beaches and top-notch restaurants in this destination. Leave some time to check out the marina and museums during your trip.

What are some of the best holiday rentals that Sheboygan has to offer?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This highly rated holiday home rental in Sheboygan is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games. Our travellers also rate REMODELED HOME ON LAKE MICHIGAN as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 90 Expedia holiday rentals in Sheboygan for a memorable holiday.

What’s there to see and do in Sheboygan?

Enjoy the outdoors at Lake Michigan and Kohler-Andrae State Park, or simply take in cultural attractions like John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. While here, Blue Harbor Resort & Conference Center Water Park and Whistling Straits Golf Course are other places worth a visit.

What’s a holiday rental in Sheboygan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheboygan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.

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