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Compare 234 Vacation Homes in Sheboygan with updated reviews, rates, and availability.

"We stayed for Thanksgiving week. It met my expectations completely! "

AED 1,313 total

includes taxes & fees

27 Jan - 28 Jan

"Such a cozy spot to spend a special weekend getaway! Mark allowed our 2 pups to join and did everything to make sure we had a comfortable stay. The view was outstanding, the home was spotless and the art gallery was so cool. We felt comfortable from the moment we walked in. Highly recommend!"

A sunny riverfront deck featuring loungers, a gas-fire table, and a coffee bar.

"Very nice townhome with lots of toys (games) for those who want to hang out. Tried to use the gas heater on deck overlooking the River but, it wouldn’t light."

"We just love everything about this place! It's super clean, beautifully decorated (and so festive around the holidays!), cozy, comfortable and in such a peaceful location. The hosts are always great too. This is our third time coming around the holidays and we always look forward to it. Maybe this year we'll try to go in the summer too :) "

AED 543 total

includes taxes & fees

27 Jan - 28 Jan

"We love staying here and will be back next year!"

Ultra private lakefront home located on Lake Michigan shoreline.

"We stayed in the fall with family ranging from 7-65. The beach and view was so beautiful and relaxing. There was plenty of room to spread out or all be together. The games in the basement were the highlight for all ages. "

"This home had everything we needed for a relaxing family stay. We played games in front of the fire and exercised our dog in the (surprise!) fenced-in backyard. "

Sandy beachfront right outside the front door

"Great location and very welcoming"

"Great house. Super clean ans spacious. We hosted family Christmas. Everything was perfect. Hope to stay again next year."

"We’ve stayed here numerous times and it’s always been fine. "

Sheboygan Vacation Rental | 1BR | 1BA | 2 Steps to Enter | 860 Sq Ft

"We just stayed there a few weeks ago and when we left we said we would definitely stay here again! Well equipped, exceptionally clean, and well located. Nice yard in the back for doggies, and the treats were nice! Management was very accommodating and easy to communicate with. Rick Doerr "

"So interesting and comfy atmosphere. We loved all the attention to detail. Great amneties. Definitely going back!"

Sheboygan Vacation Rental | 2BR | 1.5BA | 1,200 Sq Ft | Stairs Required

"My family and I were visiting family in Sheboygan over Christmas. The owner decorated the condo with a Christmas tree and other holiday decor. This condo was by far one of the most well put together condos we have stayed in. The toiletries in the condo were all high-end products. The condo was in a great location, property manager was responsive, and very clean. My family and I would definitely stay at the condo again. This condo is definitely a 5-star property. "

Bring along your boat, toys, and fishing poles. Two kayaks included.

"The Red Barn is a Historic Icon in the Two Rivers Community that has been beautifully restored and modernized making is a perfect vacation spot for our family. Many memories were created here; from the grandchildren learning to fish from the dock, catching enormous salmon from the lake to middle daughter getting engaged on this trip!!!"

Elkhart Lake Vacation Rental | 3BR | 2BA | 1,100 Sq Ft | Stairs Required

"Great stay, great location!"

"We wish we lived here."

AED 896 total

includes taxes & fees

6 Feb - 7 Feb

"This home is warm and cozy and perfect for a family. Right across the street from mariner's trail. Has everything needed to be comfortable. I also worked fromThe house and the WiFi worked great."

AED 830 total

includes taxes & fees

24 Jan - 25 Jan

"The house is amazing, My husband and I used the property for ourselves and our wedding party. It fit 24 people amazingly! The host was amazing and very responsive and SO accommodating!! Just an amazing place to be and relax between all the wedding things. If I could give more stars I absolutely would!! I loved it here!"