Sheboygan County Holiday Rentals

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Top Holiday Rentals Destinations in Sheboygan County

Our top choices for Sheboygan County holiday rentals

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$243
includes taxes & fees
3 Sept - 4 Sept
Grandstay Residential Suites Hotel - Sheboygan

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

9.6 out of 10, Exceptional, (202)
"The house is beautiful and the location can't be beat! "
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Victorian Inn Elkhart Lake Wisconsin

4.0 star property
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
Victorian Inn Elkhart Lake Wisconsin

Fall dates available at SurfDaze!

10.0 out of 10, Exceptional, (106)
"We've been going to this area of Michigan beach for several years as a spring experience and this is our favorite lakefront vrbo. "
Fall dates available at SurfDaze!

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 !

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

10.0 out of 10, Exceptional, (107)
"Great place to hang out and relax. Everything was thought of, which made it easy to enjoy."
The price is AU$280
includes taxes & fees
11 Sept - 12 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

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
27 Sept - 28 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

Riverview Getaway

9.8 out of 10, Exceptional, (24)
"Great place to stay, great host!"
Riverview Getaway

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$591
includes taxes & fees
1 Sept - 2 Sept
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Rare Find! Huge Beach & Luxe Woodsy Cabin

10.0 out of 10, Exceptional, (85)
"Property is very relaxing and host was super helpful and responsive. "
Rare Find! Huge Beach & Luxe Woodsy Cabin

Edgewater Escape: 4 Bedroom, Sleeps 14!

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

October Dates available!

10.0 out of 10, Exceptional, (133)
"Lovely "
October Dates available!

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

The Esker Ridge Chalet, Pristine Elkhart Solitude

10.0 out of 10, Exceptional, (58)
"Wonderful place, so quiet and nature surrounding the location. So close to Elkhart Lake and yet you wouldn't realize it when on the property. Five Stars!"
The price is AU$425
includes taxes & fees
3 Sept - 4 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude

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
2 Sept - 3 Sept
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Halloween on a Friday? Spooky opportunity to hunker down in an old mansion.

10.0 out of 10, Exceptional, (82)
"Great location"
Halloween on a Friday? Spooky opportunity to hunker down in an old mansion.
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 County Hotel Reviews

Find out more about Sheboygan County

Find out more about Sheboygan County

Everything you need to know about Sheboygan County 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 County 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 County holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sheboygan County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan County. 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 County 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 County holiday rentals we have chosen for you start as low as AU$203 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Sheboygan County rentals

At Expedia, we put the best Sheboygan County 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 County 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 County 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 County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.