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Aug 22 - Aug 24
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Aug 29 - Aug 31
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Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Vacation Homes in Sheboygan

Gleason's Chouse
Interior

Gleason's Chouse

10.0 out of 10, Exceptional, (37)
"Looking to unwind & relax from the daily demands of being moms & wives, a friend and I chose Gleason's Chouse for its central location to all the local hiking! We were pleasantly surprised by the charm and detail put into the house. It was comfortable and inviting! Would definitely stay again!"
The price is ￥19,871
￥28,418 total
includes taxes & fees
Aug 19 - Aug 20
Gleason's Chouse
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 ￥264,942
￥457,580 total
includes taxes & fees
Aug 25 - Aug 26
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
Outdoor dining

Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.

9.8 out of 10, Exceptional, (69)
"The place worked out perfect for our needs"
The price is ￥49,456
￥78,352 total
includes taxes & fees
Sep 15 - Sep 16
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
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, (2)
"Wonderful place! "
The price is ￥52,988
￥90,532 total
includes taxes & fees
Aug 18 - Aug 19
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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, (107)
"Great place to hang out and relax. Everything was thought of, which made it easy to enjoy."
The price is ￥22,079
￥26,399 total
includes taxes & fees
Sep 11 - Sep 12
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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, (170)
"Back again for another visit, wonderful as usual. We love this house and the ownwrs hospitality! We will be booking again!"
The price is ￥29,806
￥48,994 total
includes taxes & fees
Aug 23 - Aug 24
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Property grounds

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

10.0 out of 10, Exceptional, (26)
"Every thing was great. "
The price is ￥24,875
￥49,117 total
includes taxes & fees
Sep 6 - Sep 7
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
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 ￥29,291
￥40,374 total
includes taxes & fees
Aug 19 - Aug 20
The Esker Ridge Chalet, Pristine Elkhart Solitude
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

10.0 out of 10, Exceptional, (36)
"Loved it. Cute place, good parking, close to everything."
The price is ￥39,079
￥62,064 total
includes taxes & fees
Aug 28 - Aug 29
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Stunning private home hidden in the woods. Can sleep 11 guests
Dining

Stunning private home hidden in the woods. Can sleep 11 guests

10.0 out of 10, Exceptional, (10)
"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 ￥84,649
￥102,039 total
includes taxes & fees
Aug 19 - Aug 20
Stunning private home hidden in the woods. Can sleep 11 guests
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10.0 out of 10, Exceptional, (3)
"Coastal Comfort was very clean, pleasantly decorated and comfortable. It is within driving distance to the lake as well as restaurants in Sheboygan. Perfect stay for the two of us. "
The price is ￥16,927
￥29,404 total
includes taxes & fees
Sep 2 - Sep 3
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
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, (1)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
The price is ￥16,927
￥29,404 total
includes taxes & fees
Sep 2 - Sep 3
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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 ￥21,343
￥34,751 total
includes taxes & fees
Sep 16 - Sep 17
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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, (31)
"This is our 4th year staying at this great property!"
The price is ￥44,157
￥70,966 total
includes taxes & fees
Aug 20 - Aug 21
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Interior

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

9.8 out of 10, Exceptional, (149)
"Very clean and beautiful deck with views of Lake Michigan."
The price is ￥45,923
￥82,863 total
includes taxes & fees
Sep 7 - Sep 8
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Executive Beachfront Villa: Sleeps 8!
Fridge, microwave, oven, stovetop

Executive Beachfront Villa: Sleeps 8!

2.0 star property
9.0 out of 10, Wonderful, (2)
"The home was great. The location was great. It was perfect for a night up at blue Harbor area to enjoy the restaurants and coffee shops."
The price is ￥28,702
￥67,495 total
includes taxes & fees
Sep 17 - Sep 18
Executive Beachfront Villa: Sleeps 8!
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (33)
"The space and location were great! Communication was quick and thorough. "
The price is ￥24,286
￥65,823 total
includes taxes & fees
Sep 2 - Sep 3
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Road America, Elkhart Lake!
Terrace/patio

Road America, Elkhart Lake!

The price is ￥26,200
￥55,578 total
includes taxes & fees
Sep 16 - Sep 17
Road America, Elkhart Lake!
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Fridge, microwave, oven, stovetop

Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

10.0 out of 10, Exceptional, (10)
"Great house, great location, very well taken care of and meticulous accommodations. Definitely recommend and would stay again."
The price is ￥61,673
￥117,111 total
includes taxes & fees
Sep 8 - Sep 9
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
Beautiful Historic Home near Downtown
Dining

Beautiful Historic Home near Downtown

9.8 out of 10, Exceptional, (8)
"A gorgeously designed, spacious and well-appointed house. Convenient to a bunch of small Wisconsin towns and activities. Don’t sleep on the Hamilton Type Museum! "
The price is ￥75,146
￥123,046 total
includes taxes & fees
Aug 30 - Aug 31
Beautiful Historic Home near Downtown
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

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

10/10 Excellent
"All good. Desk guy super friendly. Quiet. "
Mike 1-night trip
Posted 2 days ago
Comfort Inn & Suites Sheboygan I-43