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Search Vacation Homes in Sheboygan

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Dec 19 - Dec 21

Vacation Homes in Sheboygan

Interior
Gleason's Chouse
Gleason's Chouse
10.0 out of 10, Exceptional, (41)
"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. "
United States
Miranda W.
$183 nightly
The price is $193
Oct 27 - Oct 28
Total with taxes and fees
Gleason's Chouse
Property grounds
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
10.0 out of 10, Exceptional, (30)
"We came just to relax and have fun. We enjoyed sitting out on the patio with our dog and books and having a bonfire in the fire pit. The home is very well labeled and cozy—we loved it! "
United States
Jeremy E.
$220 nightly
The price is $250
Oct 31 - Nov 1
Total with taxes and fees
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Private kitchen
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
2.0 star property
9.6 out of 10, Exceptional, (12)
"A warm and cozy place to stay. Beautifully decorated and friendly hosts. Would stay again anytime we’re in Sheboygan."
United States
Rebecca S.
$135 nightly
The price is $153
Oct 27 - Oct 28
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
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, (112)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
United States
Shelby L.
$160 nightly
The price is $169
Nov 3 - Nov 4
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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 ."
United States
Brenda J.
$2,872 nightly
The price is $3,260
Nov 3 - Nov 4
Total with taxes and fees
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
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."
United States
Bernardine B.
$241 nightly
The price is $274
Oct 27 - Oct 28
Total with taxes and fees
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
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"
United States
Stacy P.
$169 nightly
The price is $192
Nov 4 - Nov 5
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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"
United States
William
$318 nightly
The price is $335
Nov 2 - Nov 3
Total with taxes and fees
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Fridge, oven, stovetop, dishwasher
Surfside Retreat – Walk to Lake
Surfside Retreat – Walk to Lake
$253 nightly
The price is $257
Nov 16 - Nov 17
Total with taxes and fees
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, (38)
"Quick overnighter in Sheboygan with girlfriends. There were 6 of us and we were able to bunk up comfortably. Beds were comfy, everything was clean and well stocked. We have a lovely night here!"
United States
Carrie H.
$330 nightly
The price is $375
Nov 12 - Nov 13
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Fridge, microwave, oven, stovetop
Sheboygan Riverside Condo
Sheboygan Riverside Condo
2.0 star property
$227 nightly
The price is $231
Oct 29 - Oct 30
Total with taxes and fees
Sheboygan Riverside Condo
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! "
United States
Colleen & Mark G.
$582 nightly
The price is $614
Oct 27 - Oct 28
Total with taxes and fees
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
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."
United States
Will C.
$914 nightly
The price is $964
Oct 27 - Oct 28
Total with taxes and fees
Beautiful private home hidden in the woods. Can sleep 11 guests
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!"
United States
Gregory
$260 nightly
The price is $274
Oct 28 - Oct 29
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
Terrace/patio
Road America, Elkhart Lake!
Road America, Elkhart Lake!
$372 nightly
The price is $375
Oct 27 - Oct 28
Total with taxes and fees
Road America, Elkhart Lake!
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. "
United States
Dawn C.
$457 nightly
The price is $482
Oct 31 - Nov 1
Total with taxes and fees
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
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! "
United States
Lisa W.
$463 nightly
The price is $488
Oct 27 - Oct 28
Total with taxes and fees
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger
Interior
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
9.8 out of 10, Exceptional, (154)
"This rental gave us a home away from home with a gorgeous view of the lake from several of the rooms. It had everything we needed and more. "
United States
Linda K.
$507 nightly
The price is $575
Oct 30 - Oct 31
Total with taxes and fees
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
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, (2)
" We enjoyed our stay very much. The house is lovely, spacious, and clean. The property is quite big and provides an excellent space to walk or room for younger children to play. Several family members enjoyed a walk about after our drive on Saturday. The house was perfect for our group, and the living room was our gathering place for Saturday evening as well as Sunday morning. We cooked our evening meal and our morning breakfast in the kitchen. The only minor issue was that our group had 9...
United States
Paul & Jacqleene M.
$758 nightly
The price is $799
Oct 27 - Oct 28
Total with taxes and fees
5 min from Road America. Great yard and plenty of parking
Smart TV
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
10.0 out of 10, Exceptional, (19)
"Our stay was wonderful and the property was in a perfect location with all the amenities. Would definitely stay again when in the area. "
United States
Suzette Z.
$528 nightly
The price is $599
Nov 2 - Nov 3
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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

Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan

10/10 Excellent
"Very clean."
Roben 1-night trip
Posted 2 days ago
Home2 Suites By Hilton Sheboygan

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
732
Accommodation
273 Vacation Homes
Lowest Price
$169
Highest Price
$3,260

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