Sheboygan Vacation Homes

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Our top choices for Sheboygan holiday homes

A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

1. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan

Brian L.

HK$1,433 total

includes taxes & fees

27 Nov - 28 Nov

A living room with a fireplace, a large clock, and a dining area with wooden furniture.

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

Oostburg

Cheryl

HK$1,141 total

includes taxes & fees

11 Nov - 12 Nov

A modern living room with a sofa, two chairs, a coffee table, a ceiling fan, and a large window with curtains.

3. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Sheboygan

Tonja K.

HK$1,388 total

includes taxes & fees

10 Nov - 11 Nov

A swimming pool with lounge chairs, a lifeguard tower, and a multi-story building in the background.

4. Victorian Inn #241 | 2 Queen Beds

Elkhart Lake

HK$1,354 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

Sheboygan

Jean S.

HK$2,825 total

includes taxes & fees

6 Dec - 7 Dec

A cabin with a deck, a covered porch, and a paved driveway.

6. The Esker Ridge Chalet, Pristine Elkhart Solitude

Elkhart Lake

Barbara

HK$2,035 total

includes taxes & fees

10 Nov - 11 Nov

7. Beachfront Paradise: King Suite - Sleeps 8!

Sheboygan

Nina S.

HK$4,869 total

includes taxes & fees

10 Nov - 11 Nov

A living room with a sofa, coffee table, and TV.

8. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Sheboygan

Gregory D.

HK$4,494 total

includes taxes & fees

13 Nov - 14 Nov

A hallway with a wooden floor, a window on the left, and a plant on the right.

9. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Sheboygan

Nicole B.

HK$2,554 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

10. The Links! - Luxury Golf Retreat with Golf Simulator

Sheboygan

Kristian N.

HK$4,691 total

includes taxes & fees

10 Nov - 11 Nov

An outdoor seating area with a view of a lake, surrounded by trees and a barbecue grill.

11. New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Two Rivers

Tom & Jenny S.

HK$1,824 total

includes taxes & fees

10 Nov - 11 Nov

A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

12. Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Plymouth

Cristy

HK$4,362 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

13. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Sheboygan

Brad T.

HK$7,581 total

includes taxes & fees

10 Nov - 11 Nov

A modern house with a dark exterior, a yellow front door, and a well-maintained garden with various plants.

14. Private Oasis•Point Beach State Park•Lake Michigan

Two Rivers

HK$2,258 total

includes taxes & fees

19 Nov - 20 Nov

A room with a wooden ceiling, large windows, and a seating area with two chairs and a table.

15. 1 Mi to Shore: Lake Michigan Retreat w/ Game Room!

Two Rivers

Kelly S.

HK$4,325 total

includes taxes & fees

10 Nov - 11 Nov

A spacious lobby with leather sofas, a chandelier, a large TV, and a foosball table.

16. Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Kiel

Ryan K.

HK$3,734 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with white cabinetry and a dining area with a white table and chairs.

17. Road America, Elkhart Lake!

Elkhart Lake

HK$2,882 total

includes taxes & fees

8 Dec - 9 Dec

A wooden deck with a bench, a door with frosted glass, and two wall-mounted lights.

18. Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Reedsville

Jason R.

HK$3,424 total

includes taxes & fees

10 Nov - 11 Nov

A kitchen with wooden cabinets, a stove, a dishwasher, and a window with a view of trees.

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

New Holstein

Doug S.

HK$2,486 total

includes taxes & fees

15 Nov - 16 Nov

An outdoor patio with a hot tub, string lights, and a covered seating area.

20. The Pines-Hike, Hunt, Hot tub Sleeps 9

Cascade

Luke L.

HK$4,521 total

includes taxes & fees

18 Nov - 19 Nov

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Top Sheboygan Hotel Reviews

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

10/10 Excellent

"We had a great stay and the view is breathtaking! Nothing like cooking in the kitchen and staring out at beautiful Lake Michigan! The property was clean and the cupboards were well stocked with all the necessities for our stay. I loved walking the neighborhood with my dog and there’s so many beautiful parks close by. Mark our host was great at communicating and we truly loved our stay in Sheboygan! We will definitely be back!!!"

Comfort Inn & Suites Sheboygan I-43

8/10 Good

"Room was bigger than expected. Breakfast was better than expected as it included oatmeal cookies and bacon! Hotel is very nice and 5 star in everyday except the pool. Paint was peeling from the walls inside the hot tub, pool windows were extremely dirty, and the floor inside the big pool looked brown and dingy. I would stay again, but probably not use the pool."

REMODELED HOME ON LAKE MICHIGAN

10/10 Excellent

"Perfect place for girl’s weekend. The view of Lake Michigan was gorgeous. It had enough living room furniture to accommodate our group of four as well as a large table for dining and card playing. The kitchen was newer and was stocked with the essentials. All three bedrooms were spacious. Laying clean towels on each bed when arrived was a nice touch."

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