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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan
In four months
30 Jan - 1 Feb
Gleason's Chouse
Interior

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 HK$1,051
HK$1,503 total
includes taxes & fees
13 Oct - 14 Oct
Gleason's Chouse
The Beach town bungalow
Fridge, microwave, oven, stovetop

The Beach town bungalow

2.0 star property
The price is HK$700
HK$1,487 total
includes taxes & fees
9 Oct - 10 Oct
The Beach town bungalow
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Fridge, microwave, oven, stovetop

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 HK$2,802
HK$4,746 total
includes taxes & fees
10 Oct - 11 Oct
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Wyatt's Country Home - King Bed!
Fridge, microwave, oven, stovetop

Wyatt's Country Home - King Bed!

10.0 out of 10, Exceptional, (17)
"Beautiful property and perfect location!"
The price is HK$1,051
HK$1,889 total
includes taxes & fees
12 Oct - 13 Oct
Wyatt's Country Home - King Bed!
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Exterior

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 HK$14,009
HK$25,353 total
includes taxes & fees
16 Oct - 17 Oct
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
3 bedrooms, iron/ironing board, WiFi, bed sheets

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

10.0 out of 10, Exceptional, (2)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
The price is HK$887
HK$1,537 total
includes taxes & fees
9 Oct - 10 Oct
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Surfside Retreat – Walk to Lake
Fridge, oven, stovetop, dishwasher

Surfside Retreat – Walk to Lake

The price is HK$732
HK$2,026 total
includes taxes & fees
9 Oct - 10 Oct
Surfside Retreat – Walk to Lake
Luxury Suites #1
Private kitchen

Luxury Suites #1

The price is HK$1,471
HK$2,318 total
includes taxes & fees
13 Oct - 14 Oct
Luxury Suites #1
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Exterior detail

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 HK$1,576
HK$2,591 total
includes taxes & fees
16 Oct - 17 Oct
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

9.8 out of 10, Exceptional, (6)
"We found this location to be the perfect balance during our stay. We were a short drive away from all the places we hoped to go. Downtown, shopping, and the coast were just minutes away. Despite this luxury, the neighborhood we were in was quiet, private and removed from the hustle of crowds and traffic. The property was very well cared for and beautifully decorated. We all had plenty of room to stretch out and prepare for an event we were attending. Grabbing a snack or a meal was a breeze with...
The price is HK$799
HK$1,436 total
includes taxes & fees
9 Oct - 10 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Fridge, microwave, oven, stovetop

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 HK$1,107
HK$2,016 total
includes taxes & fees
22 Oct - 23 Oct
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
3 Min to Road America, outdoor deck, grill, & fire table
Lobby

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 HK$2,724
HK$6,052 total
includes taxes & fees
20 Oct - 21 Oct
3 Min to Road America, outdoor deck, grill, & fire table
Road America, Elkhart Lake!
Terrace/patio

Road America, Elkhart Lake!

The price is HK$1,362
HK$2,916 total
includes taxes & fees
9 Oct - 10 Oct
Road America, Elkhart Lake!
Sheboygan Riverside Condo
Fridge, microwave, oven, stovetop

Sheboygan Riverside Condo

2.0 star property
The price is HK$1,261
HK$2,097 total
includes taxes & fees
13 Oct - 14 Oct
Sheboygan Riverside Condo
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

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 HK$1,090
HK$1,314 total
includes taxes & fees
3 Nov - 4 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Beautiful private home hidden in the woods. Can sleep 11 guests
Dining

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 HK$4,973
HK$5,994 total
includes taxes & fees
9 Oct - 10 Oct
Beautiful private home hidden in the woods. Can sleep 11 guests
The Esker Ridge Chalet, Pristine Elkhart Solitude
Exterior

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 HK$1,549
HK$2,143 total
includes taxes & fees
14 Oct - 15 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Property grounds

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 HK$2,335
HK$3,753 total
includes taxes & fees
20 Oct - 21 Oct
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
LUX Uptown Escape - The Trester
Terrace/patio

LUX Uptown Escape - The Trester

9.4 out of 10, Exceptional, (10)
"Historic beauty of a home. Loved being able to walk to restaurants, art museum and more. Wonderful accommodations. "
The price is HK$973
HK$1,873 total
includes taxes & fees
16 Oct - 17 Oct
LUX Uptown Escape - The Trester
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Fridge, microwave, oven, stovetop

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

10.0 out of 10, Exceptional, (2)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
The price is HK$1,219
HK$1,975 total
includes taxes & fees
21 Oct - 22 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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

Harbor Winds Hotel

Harbor Winds Hotel

10/10 Excellent
"The location was convenient to the many things to do in Sheboygan. The woman at check in was friendly. The room was nice, though a little dusty and there was makeup on one of the towels, as well as a long white hair on a lamp. Overall was nice stay despite those minor issues. "
Zach 2-night trip
Posted 2 days ago
Harbor Winds Hotel

Find out more about Sheboygan

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
497
Accommodation
265 Vacation Homes
Lowest Price
HK$1,314
Highest Price
HK$25,353