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Search Vacation Homes in Sheboygan

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Check prices for these dates

In two weeks
Dec 12 - Dec 14
In two months
Jan 23 - Jan 25
In three months
Feb 20 - Feb 22
In four months
Mar 20 - Mar 22

Vacation Homes in Sheboygan

Exterior
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Vacation Home in Oostburg

10.0 out of 10, Exceptional, (116)
"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.
$150 nightly
The price is $158
Dec 1 - Dec 2
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Property grounds
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

Vacation Home in Two Rivers

10.0 out of 10, Exceptional, (31)
"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.
$225 nightly
The price is $255
Nov 26 - Nov 27
Total with taxes and fees
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Fridge, microwave, oven, stovetop
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach

Vacation Home in Two Rivers

9.8 out of 10, Exceptional, (37)
"House worked well for what we needed. Will look to book again if in the area another time. "
United States
Jodi S.
$159 nightly
The price is $180
Dec 1 - Dec 2
Total with taxes and fees
Cate's Place: Charming home just minutes from Ice Age Trail & Neshotah Beach
Private kitchen
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

Vacation Home in Ellis Historical District

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
Nov 26 - Nov 27
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Fridge, microwave, oven, stovetop
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

Vacation Home in Sheboygan

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.
$173 nightly
The price is $197
Dec 2 - Dec 3
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Exterior
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Vacation Home in Fond du Lac

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
Dec 1 - Dec 2
Total with taxes and fees
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater
Fridge, oven, stovetop, dishwasher
Surfside Retreat – Walk to Lake

Vacation Home in Ellis Historical District

$243 nightly
The price is $246
Dec 3 - Dec 4
Total with taxes and fees
Surfside Retreat – Walk to Lake
Fridge, microwave, oven, stovetop
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (38)
"Very clean, cute, great communication, location & walkability! "
United States
Sandee M.
$355 nightly
The price is $403
Dec 10 - Dec 11
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Dining
Beautiful private home hidden in the woods. Can sleep 11 guests

Vacation Home in Plymouth

10.0 out of 10, Exceptional, (14)
"Great place to get away for the weekend. Our family fit very comfortably. The house was clean, and very well organized. "
United States
Liliana M.
$914 nightly
The price is $964
Nov 25 - Nov 26
Total with taxes and fees
Beautiful private home hidden in the woods. Can sleep 11 guests
Smart TV
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (21)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
$352 nightly
The price is $399
Nov 25 - Nov 26
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Outdoor dining
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.

Vacation Home in Two Rivers

9.8 out of 10, Exceptional, (70)
"The place worked out perfect for our needs"
United States
Paul S.
$234 nightly
The price is $266
Nov 29 - Nov 30
Total with taxes and fees
Cozy home near Lake Michigan. Easy drive to Green Bay, Door County & Sheboygan.
Exterior detail
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Vacation Home in New Holstein

10.0 out of 10, Exceptional, (173)
"Great place would go back"
United States
William
$318 nightly
The price is $335
Dec 5 - Dec 6
Total with taxes and fees
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!
Property grounds
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Vacation Home in Reedsville

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
Nov 30 - Dec 1
Total with taxes and fees
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America
Fridge, microwave, oven, stovetop
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler

Vacation Home in Kiel

2.0 star property
10.0 out of 10, Exceptional, (3)
"Wonderful place! "
United States
Colleen & Mark G.
$576 nightly
The price is $608
Nov 30 - Dec 1
Total with taxes and fees
Luxury Historic Rental in Kiel minutes to Elkhart Lake, Road America and Kohler
Terrace/patio
Road America, Elkhart Lake!

Vacation Home in Elkhart Lake

8.0 out of 10, Very Good, (1)
$372 nightly
The price is $375
Nov 25 - Nov 26
Total with taxes and fees
Road America, Elkhart Lake!
Interior
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

Vacation Home in Two Rivers

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.
$496 nightly
The price is $563
Dec 1 - Dec 2
Total with taxes and fees
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.
Terrace/patio
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.

Vacation Home in Campbellsport

2.0 star property
$1,285 nightly
The price is $1,356
Nov 30 - Dec 1
Total with taxes and fees
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Terrace/patio
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger

Vacation Home in Cascade

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.
$461 nightly
The price is $486
Dec 2 - Dec 3
Total with taxes and fees
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger
Fridge, microwave, oven, stovetop
5 min from Road America. Great yard and plenty of parking

Vacation Home in Elkhart Lake

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.
$1,016 nightly
The price is $1,072
Dec 1 - Dec 2
Total with taxes and fees
5 min from Road America. Great yard and plenty of parking
Fridge, microwave, oven, stovetop
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.

Vacation Home in Sheboygan

10.0 out of 10, Exceptional, (12)
"This is the best-executed rental home I've stayed in. The kitchen is packed with cookware etc., the beach supplies are ample, and the furniture is comfortable. Everything was as-advertised. It was a delight to stay here. My only caution is the quite steep staircase that could slip up those who aren't sure-footed."
United States
Jon V.
$799 nightly
The price is $907
Nov 30 - Dec 1
Total with taxes and fees
Luxury Lake House-4Bed-2Bath-NEW Renovation 2023-Walk to Beach, Dining, & More.
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"Very clean room, spacious, easy check in and check out."
Stephanie 1-night trip
Posted 3 days ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan

Sheboygan Vacation Homes information

Number of reviews
733
Accommodation
262 Vacation Homes
Lowest Price
$153
Highest Price
$3,260

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