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Holiday Homes in Sheboygan

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Featured Holiday Homes in Sheboygan

Interior
Gleason's Chouse
Gleason's Chouse
10.0 out of 10, Exceptional, (40)
"The house was such a unique and fun place to stay, we had such a great weekend and experience there. My spouse is already talking about coming back someday soon. The neighborhood felt safe and it was easy to get around to any place we needed to. It was clean and stocked with extra amenities that anyone might need on a trip. "
The price is AU$300
includes taxes & fees
23 Oct - 24 Oct
Gleason's Chouse
Exterior
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (111)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
The price is AU$263
includes taxes & fees
3 Nov - 4 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Fridge, microwave, oven, stovetop
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
9.8 out of 10, Exceptional, (37)
"Loved it. Cute place, good parking, close to everything."
The price is AU$407
includes taxes & fees
19 Oct - 20 Oct
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Exterior
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
4.0 star property
10.0 out of 10, Exceptional, (1)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
The price is AU$5,070
includes taxes & fees
23 Oct - 24 Oct
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Fridge, microwave, oven, stovetop
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (4)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
The price is AU$308
includes taxes & fees
21 Oct - 22 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Fridge, microwave, oven, stovetop
Wyatt's Country Home - King Bed!
Wyatt's Country Home - King Bed!
10.0 out of 10, Exceptional, (17)
"Beautiful property and perfect location!"
The price is AU$366
includes taxes & fees
19 Oct - 20 Oct
Wyatt's Country Home - King Bed!
Exterior detail
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
10.0 out of 10, Exceptional, (173)
"Great place would go back"
The price is AU$519
includes taxes & fees
24 Oct - 25 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Terrace/patio
LUX Uptown Escape - The Trester
LUX Uptown Escape - The Trester
9.6 out of 10, Exceptional, (11)
"Clean, great location, nice space, easy walking to restaurants/bars"
LUX Uptown Escape - The Trester
Fridge, microwave, oven, stovetop
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
2.0 star property
10.0 out of 10, Exceptional, (3)
"Wonderful place! "
The price is AU$956
includes taxes & fees
18 Oct - 19 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Fridge, oven, stovetop, dishwasher
Surfside Retreat – Walk to Lake
Surfside Retreat – Walk to Lake
The price is AU$421
includes taxes & fees
12 Nov - 13 Nov
Surfside Retreat – Walk to Lake
Fridge, microwave, oven, stovetop
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
10.0 out of 10, Exceptional, (37)
"The property was quite cozy with a great fenced-in backyard, conveniently located near the little downtown and Lake Michigan. Couldn't have asked for more!"
The price is AU$634
includes taxes & fees
4 Nov - 5 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Dining
Beautiful private home hidden in the woods. Can sleep 11 guests
Beautiful private home hidden in the woods. Can sleep 11 guests
10.0 out of 10, Exceptional, (14)
"This VRBO was everything that the listing described and more. The host was very easy to communicate with and helped make sure we had a great stay."
The price is AU$1,498
includes taxes & fees
19 Oct - 20 Oct
Beautiful private home hidden in the woods. Can sleep 11 guests
Fridge, microwave, oven, stovetop
Sheboygan Riverside Condo
Sheboygan Riverside Condo
2.0 star property
The price is AU$403
includes taxes & fees
19 Oct - 20 Oct
Sheboygan Riverside Condo
Exterior
The Esker Ridge Chalet, Pristine Elkhart Solitude
The Esker Ridge Chalet, Pristine Elkhart Solitude
10.0 out of 10, Exceptional, (58)
"Wonderful place, so quiet and nature surrounding the location. So close to Elkhart Lake and yet you wouldn't realize it when on the property. Five Stars!"
The price is AU$426
includes taxes & fees
22 Oct - 23 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
Property grounds
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
9.8 out of 10, Exceptional, (32)
"Great place for family to stay for wedding of grandson. "
The price is AU$749
includes taxes & fees
17 Oct - 18 Oct
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Terrace/patio
Road America, Elkhart Lake!
Road America, Elkhart Lake!
The price is AU$582
includes taxes & fees
26 Oct - 27 Oct
Road America, Elkhart Lake!
Terrace/patio
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger
10.0 out of 10, Exceptional, (33)
"Such a gem of a place! Beautiful and amazing property and so well appointed! Highly recommend - host is extremely accommodating, wonderful communication and kind. Master bedroom is like a penthouse suite! We are already planning our next stay! "
The price is AU$758
includes taxes & fees
21 Oct - 22 Oct
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger
Outdoor dining
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
9.8 out of 10, Exceptional, (70)
"The place worked out perfect for our needs"
The price is AU$574
includes taxes & fees
23 Oct - 24 Oct
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
Fridge, microwave, oven, stovetop
5 min from Road America. Great yard and plenty of parking
5 min from Road America. Great yard and plenty of parking
10.0 out of 10, Exceptional, (1)
The price is AU$1,665
includes taxes & fees
17 Oct - 18 Oct
5 min from Road America. Great yard and plenty of parking
Outdoor dining
3 Min to Road America, outdoor deck, grill, & fire table
3 Min to Road America, outdoor deck, grill, & fire table
10.0 out of 10, Exceptional, (1)
"This place was perfect for our group. We were karting at Road America, and location was a little over a mile from the gate. Newly renovated and very nice. Hosts did lots of little things to add value to our stay. Plenty to do nearby. Kids loved the basement and yard, adults hung out on patio. Would definitely stay here again. "
The price is AU$1,351
includes taxes & fees
20 Oct - 21 Oct
3 Min to Road America, outdoor deck, grill, & fire table
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Sheboygan Hotel Reviews

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent
"Nice and clean"
Roland Young 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Sheboygan

Find out more about Sheboygan

Sheboygan Holiday Homes information

Number of reviews
634
Accommodation
265 Holiday Homes
Lowest Price
AU$263
Highest Price
AU$5,070