Sheboygan County Short-Term Rentals from S$233: Search Holiday Rentals

A wooden boardwalk along a sandy beach with dunes and a clear sky.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Our top choices for Sheboygan County holiday rentals

Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

includes taxes & fees

15 Jul - 16 Jul

Updated Plymouth Home ~ 5 Mi to Road America!

Plymouth

Thiago

includes taxes & fees

10 Aug - 11 Aug

Large Backyard, Walk to Hospital: Sheboygan Abode!

Sheboygan

includes taxes & fees

12 Jul - 13 Jul

View all properties

Find holiday rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Top Sheboygan County Hotel Reviews

The American Club

10/10 Excellent

"Staff was great, cleaning services in room were exceptional with personalized notes being left for us. We'd go back for sure :)"

Siebkens Resort

10/10 Excellent

"I stayed in the oldest hotel part of this vintage resort comprised of multiple related buildings spread out around a large block. You have to realize what you are getting--a very simple square room in an historic building with last century charm and lots of beautifully maintained antiques in the halls. Small room, a real key, old fashioned minimal carpet, tiny bathroom with vintage everything, but clean, with fresh white towels and an antique looking bed with a brand new mattress and crisp white sheets. Room was air-conditioned and had black out curtains. Not modern--but exactly right in this vintage resort in a vintage town. I felt I had stepped back in time--in a good way. Continental breakfast in the old fashioned lobby was homemade granola, homemade bread and plenty of coffee. Other travelers enjoying breakfast at the dining table have been coming for years. It's that kind of place."

Inn On Woodlake

10/10 Excellent

"The entire property was lovely, we had access to all amenities and there were shuttles that took us to all restaurants and the Sports core. Our room was clean and loved the bathroom! A very nice breakfast was included and coffee available all day. Happy hour offered a free beer or glass of wine and a full bar to purchase a drink. The staff was extremely helpful. They are expanding this property and it looks fantastic"

Watershed Hotel

10/10 Excellent

"I found this to be very well maintained, clean and quiet. For a one night stay that’s all I really want. The area around the place seemed a little odd - condos next door and some sort of commercial operation across the street but no real problem with that. There was in fact a water view but it was kind of meh and not a compelling reason to pay more to stay there. The continental breakfast was basically next to nothing unless you like pre wrapped processed food items like twinkies. Crazy to see that. Funny how the better the hotel is the worse the breakfast. If you don’t care about view, location, or breakfast, then this is a really lovely little hotel."

Room 1

Change your mind

Treat yourself

Be picky

Our top choices for Sheboygan County holiday rentals

Grandstay Residential Suites Hotel - Sheboygan

Updated Plymouth Home ~ 5 Mi to Road America!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Find holiday rentals that suit your style

Top Sheboygan County Hotel Reviews

The American Club

Grandstay Residential Suites Hotel - Sheboygan

Harbor Winds Hotel

AmericInn by Wyndham Sheboygan

Siebkens Resort

The Osthoff Resort

The Oasis Hotel & Bar

Inn On Woodlake

Watershed Hotel

Sheboygan County Holiday Rentals

Change your mind

Treat yourself

Be picky

Our top choices for Sheboygan County holiday rentals

Grandstay Residential Suites Hotel - Sheboygan

Updated Plymouth Home ~ 5 Mi to Road America!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Find holiday rentals that suit your style

Top Sheboygan County Hotel Reviews

The American Club