Sheboygan Holiday Rentals

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Our top choices for Sheboygan holiday rentals

Aparthotel in Downtown Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (1,023 reviews)
"Room was very clean and perfect for a downtown stay"
United States
Jim
The price is AU$222
includes taxes & fees
30 Mar - 31 Mar
Grandstay Residential Suites Hotel - Sheboygan

Cabin in Campbellsport

Tiki Beach Campground
3.0 star property
The price is AU$148
includes taxes & fees
31 Mar - 1 Apr
Tiki Beach Campground
10.0 out of 10, Exceptional, (123 reviews)
"Our host was warm and welcoming and our accommodations were wonderful (well appointed and decorated … every detail well thought out)."
United States
Heidi E.
The price is AU$208
includes taxes & fees
9 Mar - 10 Mar
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Apartment in Manitowoc

2nd floor loft near the lake!
9.8 out of 10, Exceptional, (16 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is AU$320
includes taxes & fees
7 Mar - 8 Mar
2nd floor loft near the lake!
10.0 out of 10, Exceptional, (12 reviews)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is AU$338
includes taxes & fees
9 Mar - 10 Mar
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Aparthotel in Elkhart Lake

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin
10.0 out of 10, Exceptional, (13 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is AU$235
includes taxes & fees
9 Mar - 10 Mar
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
9.8 out of 10, Exceptional, (24 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is AU$535
includes taxes & fees
10 Mar - 11 Mar
First Floor Pet Friendly Queen Suite with Single Pull-out

Apartment in Sheboygan

*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is AU$586
includes taxes & fees
16 Mar - 17 Mar
*NEW* Sleeps 8 & Spacious!
9.2 out of 10, Wonderful, (10 reviews)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
United States
Kim K.
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.6 out of 10, Exceptional, (12 reviews)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
The price is AU$221
includes taxes & fees
6 Mar - 7 Mar
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
10.0 out of 10, Exceptional, (59 reviews)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is AU$378
includes taxes & fees
17 Mar - 18 Mar
The Esker Ridge Chalet, Pristine Elkhart Solitude

Apartment in Brillion

Luxury Suites #3
10.0 out of 10, Exceptional, (1 review)
"Apartments were clean with easy access. Centrally located entertainment room was enjoyed by my granddaughter with claw machines, games, and TV. It is a newer property and still needs a few touches, like wall decor to soften the echoes. A bench outside the individual rentsls would be nice for seating, but there's a great area out back with chairs and heating if needed. "
United States
Debby
The price is AU$419
includes taxes & fees
5 Apr - 6 Apr
Luxury Suites #3
10.0 out of 10, Exceptional, (40 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is AU$574
includes taxes & fees
8 Mar - 9 Mar
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
10.0 out of 10, Exceptional, (4 reviews)
"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$243
includes taxes & fees
10 Mar - 11 Mar
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
10.0 out of 10, Exceptional, (174 reviews)
"Great place would go back"
United States
William
The price is AU$470
includes taxes & fees
11 Mar - 12 Mar
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
9.6 out of 10, Exceptional, (10 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is AU$814
includes taxes & fees
8 Mar - 9 Mar
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
10.0 out of 10, Exceptional, (24 reviews)
"Great location!! Super clean, all we needed "
United States
Kathy P.
The price is AU$589
includes taxes & fees
6 Mar - 7 Mar
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Apartment in Sheboygan

Newly Updated! Downtown & Shore
9.8 out of 10, Exceptional, (6 reviews)
"Clean, spacious, and quiet. "
United States
Thomas S.
Newly Updated! Downtown & Shore
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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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$222 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 John Michael Kohler Arts Center, 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?

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 air conditioning 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 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 North Side Municipal Beach, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Stefanie H. Weill Center for the Performing Arts and Blue Harbor Resort & Conference Center Water 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.