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Sheboygan Holiday Rentals

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Holiday Rentals in Sheboygan

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (983)
"Nice hotel and area. Walked less than a block to a wonderful restaurant."
United States
Ericka
The price is AU$202
includes taxes & fees
19 Oct - 20 Oct
Grandstay Residential Suites Hotel - Sheboygan
First Floor Pet Friendly Queen Suite with Single Pull-out
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is AU$434
includes taxes & fees
20 Oct - 21 Oct
First Floor Pet Friendly Queen Suite with Single Pull-out
Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
The price is AU$651
includes taxes & fees
20 Oct - 21 Oct
Large Backyard, Walk to Hospital: Sheboygan Abode!
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (20)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
The price is AU$204
includes taxes & fees
21 Oct - 22 Oct
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
2nd floor loft near the lake!
9.8 out of 10, Exceptional, (15)
"It was a great stay, the location is so close to downtown and the place itself was spacious. Would highly recommend "
United States
Ian K.
The price is AU$348
includes taxes & fees
22 Oct - 23 Oct
2nd floor loft near the lake!
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
10.0 out of 10, Exceptional, (3)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is AU$309
includes taxes & fees
16 Nov - 17 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
The Beach town bungalow
2.0 star property
The price is AU$283
includes taxes & fees
16 Nov - 17 Nov
The Beach town bungalow
Wyatt's Country Home - King Bed!
10.0 out of 10, Exceptional, (17)
"Beautiful property and perfect location!"
United States
Michael T.
Wyatt's Country Home - King Bed!
Gleason's Chouse
10.0 out of 10, Exceptional, (40)
"The house was such a unique and fun place to stay, we had such a great weekend and experience there. My spouse is already talking about coming back someday soon. The neighborhood felt safe and it was easy to get around to any place we needed to. It was clean and stocked with extra amenities that anyone might need on a trip. "
United States
Miranda W.
The price is AU$301
includes taxes & fees
21 Oct - 22 Oct
Gleason's Chouse
Modern Room Near Indoor Pool
9.4 out of 10, Exceptional, (3)
"Center located and great access to pools beach etc….dog also had a blast!"
United States
John M.
The price is AU$434
includes taxes & fees
19 Oct - 20 Oct
Modern Room Near Indoor Pool
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (111)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
United States
Shelby L.
The price is AU$263
includes taxes & fees
18 Nov - 19 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.2 out of 10, Wonderful, (7)
"We found this location to be the perfect balance during our stay. We were a short drive away from all the places we hoped to go. Downtown, shopping, and the coast were just minutes away. Despite this luxury, the neighborhood we were in was quiet, private and removed from the hustle of crowds and traffic. The property was very well cared for and beautifully decorated. We all had plenty of room to stretch out and prepare for an event we were attending. Grabbing a snack or a meal was a breeze with...
United States
Aimee S.
The price is AU$288
includes taxes & fees
20 Oct - 21 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Riverfront Sheboygan Townhome w/ Grill!
3.5 star property
10.0 out of 10, Exceptional, (1)
"It was nice to be able to park in the garage. Being there felt like home away from home. Very welcoming and comfortable."
United States
Maureen
Riverfront Sheboygan Townhome w/ Grill!
Surfside Retreat – Walk to Lake
The price is AU$404
includes taxes & fees
16 Nov - 17 Nov
Surfside Retreat – Walk to Lake
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (27)
"Very spacious and clean place to stay at. Would definitely recommend this property and will likely be back when in the area"
United States
Tri
The price is AU$647
includes taxes & fees
16 Nov - 17 Nov
*NEW* Sleeps 8 & Spacious!
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is AU$288
includes taxes & fees
26 Oct - 27 Oct
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Newly Updated! Downtown & Shore
9.6 out of 10, Exceptional, (4)
"Clean, spacious, and quiet. "
United States
Thomas S.
Newly Updated! Downtown & Shore
Logan Ave Holiday House - Upper
9.4 out of 10, Exceptional, (3)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is AU$517
includes taxes & fees
16 Nov - 17 Nov
Logan Ave Holiday House - Upper
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (4)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is AU$342
includes taxes & fees
18 Nov - 19 Nov
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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.
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Top Sheboygan Hotel Reviews

Find out more about Sheboygan

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$202 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 scenic lakeside 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?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: 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. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travellers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 95 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 Bookworm Gardens, 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 Kohler-Andrae State Park 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.