Sheboygan Holiday Rentals

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Our top choices for Sheboygan holiday rentals

Tiki Beach Campground

Tiki Beach Campground
3.0 star property
Campbellsport
10.0 out of 10, Exceptional, (1 review)
"Beautiful"
United States
Angela
The price is AU$145
includes taxes & fees
22 Apr - 23 Apr
Tiki Beach Campground

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,029 reviews)
"Room was clean, staff was nice. The breakfast was pretty darn good. "
United States
andrea
The price is AU$226
includes taxes & fees
22 Apr - 23 Apr
Grandstay Residential Suites Hotel - Sheboygan

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is AU$964
includes taxes & fees
26 Apr - 27 Apr
Victorian Inn Elkhart Lake Wisconsin

Gleason's Chouse

Gleason's Chouse
Campbellsport
10.0 out of 10, Exceptional, (41 reviews)
"Incredibly decorated home. Loved staying here. "
United States
Mike L.
The price is AU$267
includes taxes & fees
26 Apr - 27 Apr
Gleason's Chouse

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Ellis Historical District
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$216
includes taxes & fees
29 Apr - 30 Apr
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is AU$230
includes taxes & fees
27 Apr - 28 Apr
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (17 reviews)
"Very clean, and tastefully decorated…would rent again:)"
United States
Kim B.
The price is AU$315
includes taxes & fees
23 Apr - 24 Apr
2nd floor loft near the lake!

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (126 reviews)
"Welcoming and accommodating host, very clean and cozy cottage, amazing fireplace "
United States
Cade R.
The price is AU$217
includes taxes & fees
28 Apr - 29 Apr
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (25 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is AU$185
includes taxes & fees
29 Apr - 30 Apr
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
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$278
includes taxes & fees
22 Apr - 23 Apr
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Super cute place with great amenities. I even got to park my car in the garage! We enjoyed our stay here!"
United States
Carolyn W.
The price is AU$337
includes taxes & fees
4 May - 5 May
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach

No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach
Two Rivers
10.0 out of 10, Exceptional, (22 reviews)
"Amazing place with exceptional hospitality. Every detail has been thoughtfully considered, from the amenities to the overall comfort. The design is beautiful, and the outdoor space offers wonderfully relaxing vibes. We’d definitely love to return—thank you for hosting us!"
United States
Aleks M.
The price is AU$369
includes taxes & fees
27 Apr - 28 Apr
No Cleaning Fee. King Bed. Cedar soaking Hot Tub, 5min walk to Beach

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
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$382
includes taxes & fees
22 Apr - 23 Apr
The Esker Ridge Chalet, Pristine Elkhart Solitude

First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out
Elkhart Lake
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$629
includes taxes & fees
26 Apr - 27 Apr
First Floor Pet Friendly Queen Suite with Single Pull-out

Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
The price is AU$561
includes taxes & fees
10 May - 11 May
Modern South Pier Condo on Sheboygan River!

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
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$781
includes taxes & fees
4 May - 5 May
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Two Rivers
10.0 out of 10, Exceptional, (34 reviews)
"The property was very nice, clean, and comfortable! The hosts were very kind and available if you needed them. A great place to stay if youre in the area!"
United States
Tara F.
The price is AU$340
includes taxes & fees
27 Apr - 28 Apr
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (41 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$623
includes taxes & fees
19 May - 20 May
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (11 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.
The price is AU$296
includes taxes & fees
26 Apr - 27 Apr
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (4 reviews)
"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$470
includes taxes & fees
10 May - 11 May
Logan Ave Holiday House - Upper
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$185 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 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 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 98 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.