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Vacation rentals in Sheboygan

Vacation rentals in Sheboygan

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Sheboygan

Guests agree: these stays are highly rated for location, cleanliness, and more.

  • Cozy Sheboygan Upper
    SUPERHOSTEntire flat · 4 guests · 1 bed · 1 bathroom
    Cozy Sheboygan Upper

    Located in the Historic Ellis Neighborhood two blocks from the beach, this 1870's home is waiting for your visit to Sheboygan. You will have easy access to downtown, the lakefront and the river boardwalk all within four blocks.

    What guests are saying:

    “Craig & Kaitlynn's apartment is very homey and comfortable. Communication was great too -- easy check in and the fastest response when the internet went down for just a moment. The location is unbeatable -- walking distance to downtown restaurants, the art museum, and the lake. We were really cozy on a warm winter night. Would definitely stay again!”

  • Lake Michigan Beach Home by Frank Lloyd Wright pro
    SUPERHOSTEntire house · 5 guests · 5 beds · 1.5 bathrooms
    Lake Michigan Beach Home by Frank Lloyd Wright pro

    Beautiful view and sand beach on Lake Michigan completely private surrounded by mature white pine trees and cedar trees. The spacious home is fully equipped with an "eat in" kitchen, dining room and living room entertainment space, den with see thru log fired fireplace, screened in porch to accommodate additional eating space, large outdoor deck with grill and fire pit. A canoe and row boat are available for the boating enthusiast, with life jackets and other floating devices.

    What guests are saying:

    “Vision of peace, serenity and comfort. This house was an adventure to find. Once pulling off the highway, just south of Sheboygan. We ventured through back woods and roads, and stumbled upon a small, quaint, well kept slew of cottages. At the very end, we were graced upon Hal's House. This Frank Loyd Wright replica, was stunning, yet simple on the outside. But once we entered, the midcentury modern furniture, 70's feel, and stunning views of Lake Michigan out of every room, caught our attention and we fell in love. We took advantage of all aspects of the house - the peninsula fireplace, and the outdoor fire pit was our favorite thing. We utilized the indoor fireplace as much as we could as we stayed during the Christmas holiday. The kitchen was well set up, with all the necessities. The open layout in the dining room, living room and den was comforting and warm. We woke up and went to sleep every day with the sounds of waves. This is a MUST stay! We will certainly have this in our memories for the rest of our lives. We loved it.”

  • Bright and Beautiful Lake Escape
    SUPERHOSTEntire house · 8 guests · 4 beds · 1 bathroom
    Bright and Beautiful Lake Escape

    Welcome to the gorgeous bluffs of Sheboygan's Lake Michigan waterfront! Our lakefront home is perfect for a romantic getaway, girls weekend, golf trip, or fun family vacation year round. Close to town, shops, bars & restaurants!

    What guests are saying:

    “Exactly as described! The home is adorable and located right on the lake, with views of the lake from the living room and dining room. The beautiful pier leads down to the water (turn on the lights for the full effect at nighttime!) and is another place to relax in privacy. We came for just a short winter-weekend getaway and were not disappointed. We rode our bikes to town (cute town!) enjoyed a fish fry at a supper club, and enjoyed cooking and laying low the entire time--exactly what we needed! Every single touch we noticed (great quality soaps, a wide selection of pillows, ample toilet paper and towels, and we loved LOVED reviewing all the books placed throughout the place). I can only imagine the place in the summer with access to the screened in porch (it was a bit cold this time of year to fully enjoy it, but we fantasized), fire pit, and water activities. We wish we could make this our home away from home, and can't wait to be back! (note to bikers: the paths were pretty snowy still, even frozen over, so we had to stay on the main streets).”

Holiday rentals for every style

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Popular amenities for Sheboygan holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Sheboygan

Cozy Sheboygan Upper
SUPERHOSTEntire flat
Cozy Sheboygan Upper
Price:£58 / night
Sheboygan Surf House "The Elbow"
SUPERHOSTEntire flat
Sheboygan Surf House "The Elbow"
Price:£40 / night
Carriage House Sheboygan, Lake access & views!
Entire guest house
Carriage House Sheboygan, Lake access & views!
Price:£81 / night
Lake Shore House-directly on Lake Michigan!
SUPERHOSTEntire house
Lake Shore House-directly on Lake Michigan!
Price:£147 / night
Lake Michigan Beach Home by Frank Lloyd Wright pro
SUPERHOSTEntire house
Lake Michigan Beach Home by Frank Lloyd Wright pro
Price:£121 / night
Furnished 1 brs for rent on a multi-monthly basis
Entire flat
Furnished 1 brs for rent on a multi-monthly basis
Price:£32 / night
Bright and Beautiful Lake Escape
SUPERHOSTEntire house
Bright and Beautiful Lake Escape
Price:£243 / night
Great spot for Kohler golf trip or family holiday!
SUPERHOSTEntire house
Great spot for Kohler golf trip or family holiday!
Price:£401 / night
Cozy bungalow in the heart of Sheboygan
Entire bungalow
Cozy bungalow in the heart of Sheboygan
Price:£61 / night
BEACHSIDE GETAWAY
SUPERHOSTEntire apartment
BEACHSIDE GETAWAY
Price:£121 / night
Beach House
SUPERHOSTEntire guest house
Beach House
Price:£130 / night
Spacious & Peaceful Home in the heart of Sheboygan
SUPERHOSTEntire house
Spacious & Peaceful Home in the heart of Sheboygan
Price:£81 / night
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