Sheboygan Vacation Homes

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Our top choices for Sheboygan holiday homes

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

Ellis Historical District

Rebecca S.

HK$1,200 total

includes taxes & fees

1 Jun - 2 Jun

Gleason's Chouse

Campbellsport

Mike L.

HK$1,513 total

includes taxes & fees

1 Jun - 2 Jun

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

Oostburg

Cade R.

HK$1,905 total

includes taxes & fees

2 Jun - 3 Jun

The Esker Ridge Chalet, Pristine Elkhart Solitude

Elkhart Lake

Scott G.

HK$2,132 total

includes taxes & fees

2 Jun - 3 Jun

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

New Holstein

William

HK$2,810 total

includes taxes & fees

18 Jun - 19 Jun

1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Two Rivers

Melissa B.

HK$3,272 total

includes taxes & fees

14 Jun - 15 Jun

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

Sheboygan

Brenda R.

HK$2,890 total

includes taxes & fees

1 Jun - 2 Jun

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

Sheboygan

Jean S.

HK$3,157 total

includes taxes & fees

31 May - 1 Jun

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Top Sheboygan Hotel Reviews

Super 8 by Wyndham Sheboygan WI

4/10 Poor

"I travel occasionally. The staff was not overly welcoming, rather curt and abrupt. The room was stark and had a little bit of an unusual odor. I was very pleased with the air conditioning. I need it to be 61 degrees when I sleep, and I slept quite well. The breakfast consisted of plain yogurt, two kinds of cereal, two kinds of toast, make your own waffles, 4 bananas, a couple of muffins, coffee, and juice. I understand the place is small, but I'm diabetic and the choices were rather limited. I often need to travel to this area. I will not stay there again, unless no other places are available. It wasn't horrible, but it's not on my top 100 list."

Beach front luxury spacious villa !

10/10 Excellent

"Beds were comfortable, and there were plenty of blankets available in the living room area. Decor was top notch and aesthetically pleasing, and the kitchen items for use were of good quality. It was nice to have beach items available to use, even if we didn’t take advantage of them. Would definitely go back for another ladies getaway!"

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent

"I didn’t catch the woman’s name, but the lady working all weekend was incredibly helpful. She gave us great recommendations for things to see and do while visiting Sheboygan, and she was so kind and welcoming. The breakfast was really good, and the hotel was in a perfect location. We would definitely stay here again if we’re ever back in town!"

Quality Inn Sheboygan North I-43

8/10 Good

"The staff--especially the young ones--were extremely helpful! It was a nice, quiet stay. The one thing, the cleaning people didn't give fresh bedding and did not make the beds when they came by (3-night stay). Maybe that's the Inn's policy and I missed that; at any rate, it's not a deal-breaker. Nor did we get fresh towels--only upon request, at least after the first night. Maybe this was a communication issue with the cleaning people: passing her in the hall, her English wasn't great, and she might have misunderstood me. Anyways, I would definitely stay there again. I would give them between a 7.5 - 7.9 rating out of 10."

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