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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, (960)
"Location and ease of parking were great!"
The price is AU$238
includes taxes & fees
2 Sept - 3 Sept
Grandstay Residential Suites Hotel - Sheboygan

Lake Michigan Home with gorgeous views, great spot for family or golf retreat

10.0 out of 10, Exceptional, (113)
"We had a great girls weekend at the house. We were able to walk to pickleball courts and enjoy a campfire by the lake. "
Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (248)
"We really enjoyed our stay. Very clean and easy check in process. Would highly recommend to anyone considering staying here. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Beach front luxury spacious villa !

10.0 out of 10, Exceptional, (66)
"Wonderful stay in a beautiful area, we hope to be back!! "
Beach front luxury spacious villa !

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

9.8 out of 10, Exceptional, (9)
The price is AU$203
includes taxes & fees
2 Sept - 3 Sept
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Vacation Paradise: 4 Bedroom, Sleeps 14!

2.0 star property
7.0 out of 10, Good, (4)
"Beautiful location."
Vacation Paradise: 4 Bedroom, Sleeps 14!

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

10.0 out of 10, Exceptional, (101)
"Excellent location, very comfortable and clean. "
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

9.8 out of 10, Exceptional, (8)
"This was our first VRBO stay. It beats any hotel stay in recent memory. The amenities exceeded our expectations. Can't wait to visit again using VRBO!"
The price is AU$627
includes taxes & fees
1 Sept - 2 Sept
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10.0 out of 10, Exceptional, (4)
"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. "
The price is AU$327
includes taxes & fees
1 Sept - 2 Sept
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Edgewater Escape: 4 Bedroom, Sleeps 14!

The price is AU$971
includes taxes & fees
17 Sept - 18 Sept
Edgewater Escape: 4 Bedroom, Sleeps 14!

BEACHSIDE GETAWAY IN SHEBOYGAN

10.0 out of 10, Exceptional, (25)
"We had a great time here! It was nice and clean, the kitchen was well-stocked, the views were awesome, beds were comfortable...i could go on and on. I have nothing negative to say about our experience. I loved being able to see the lake from the front AND back deck. The sound is so soothing and even though the weather wasnt great, it was so peaceful to drink my tea in the morning and watch the waves from the kitchen table. You are right on the water and we enjoyed a few chilly walks in the sand....
BEACHSIDE GETAWAY IN SHEBOYGAN

Lakeview Farm | Beach · Hot Tub · Theater · Views

10.0 out of 10, Exceptional, (1)
"Fun time! Very buggy by the lake but not much you can do about that. "
Lakeview Farm | Beach · Hot Tub · Theater · Views

Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

10.0 out of 10, Exceptional, (2)
"All of us, ages 5-75 had a wonderful time. Plenty of activities but also places to relax. We especially enjoyed the beautiful yard, the pool and spa & the well equipped kitchen."
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

Beachside Condo w/ Stunning Lake Views

10.0 out of 10, Exceptional, (20)
"Beautiful location and accommodations"
Beachside Condo w/ Stunning Lake Views

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

10.0 out of 10, Exceptional, (1)
"We had an awesome time!! The hosts answered all of our questions fast and helped us know things about the area. We would love to go back!"
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views

10.0 out of 10, Exceptional, (22)
"Stayed here multiple times and never disappointed."
Riverwalk Retreat - Riverfront 3BR Condo w/ Jacuzzi & Lake Michigan Views

Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony

9.8 out of 10, Exceptional, (16)
"This is a great spot in this destination. Walking distance to a great Italian restaurant and the resort with arcade and waterpark."
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony

3 Bedroom Beach House

9.4 out of 10, Exceptional, (14)
"In town for Road America event, house was spacious, cozy and comfortable. Very well kept and clean!"
3 Bedroom Beach House

REMODELED HOME ON LAKE MICHIGAN

10.0 out of 10, Exceptional, (156)
"Beautiful, clean house with spectacular views of Lake Michigan. If we are ever back in the area, we will be staying here, again!"
REMODELED HOME ON LAKE MICHIGAN

Family-Friendly House: Walk to Lake Michigan!

9.6 out of 10, Exceptional, (28)
"Very happy with the house we rented, it was very clean, well stocked, and great location. Definitely will recommend!"
Family-Friendly House: Walk to Lake Michigan!
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

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$203 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?

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 Lake Michigan Home with gorgeous views, great spot for family or golf retreat 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.