A wooden boardwalk along a sandy beach with dunes and a clear sky.

Vacation Rentals in Sheboygan County

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Our top choices for Sheboygan County vacation rentals

A spacious living area with a fireplace, a sofa, and a dining area in the background.

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,074 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥19,511
￥22,146 total
includes taxes & fees
Sep 14 - Sep 15
Grandstay Residential Suites Hotel - Sheboygan
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

2. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.6 out of 10, Exceptional, (31 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is ￥15,124
￥20,780 total
includes taxes & fees
Aug 31 - Sep 1
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A spacious living area with a wooden dining table, chairs, and a sofa. There is a staircase leading to another level, and a large window providing natural light.

3. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
10.0 out of 10, Exceptional, (24 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is ￥16,771
￥42,536 total
includes taxes & fees
Sep 8 - Sep 9
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A bedroom with a wooden bed, white bedding, and a painting of a snowy landscape.

4. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Sheboygan
9.8 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay and found the place very comfortable for our family of five. It was easy to walk down to see the lake and a quick drive to restaurants in town."
United States
Amanda
The price is ￥16,341
￥29,575 total
includes taxes & fees
Sep 1 - Sep 2
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
An indoor water park with multiple slides and play structures.

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

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (140 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥22,925
￥27,714 total
includes taxes & fees
Sep 7 - Sep 8
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

6. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (29 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is ￥17,499
￥59,434 total
includes taxes & fees
Aug 31 - Sep 1
Sleeps 8 & Spacious!
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

7. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (8 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is ￥17,775
￥51,991 total
includes taxes & fees
Sep 2 - Sep 3
Logan Ave Holiday House - Upper
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

8. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (22 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is ￥17,499
￥53,472 total
includes taxes & fees
Aug 31 - Sep 1
Beautiful & Convenient!
A spacious living room with a sofa, armchairs, a coffee table, and a TV mounted on the wall. There is a dining area in the background with a table and chairs.

9. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Sheboygan
9.8 out of 10, Exceptional, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
The price is ￥14,806
￥31,442 total
includes taxes & fees
Aug 31 - Sep 1
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A modern living room with a ceiling fan, two sofas, a coffee table, and a TV.

10. Close to Downtown & Shore | Great Location

Close to Downtown & Shore | Great Location
Sheboygan
9.0 out of 10, Wonderful, (10 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
The price is ￥17,290
￥53,248 total
includes taxes & fees
Sep 1 - Sep 2
Close to Downtown & Shore | Great Location
A bathroom with white shelves holding wicker baskets and a potted plant.

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

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (6 reviews)
"Very clean and good location; nice place for our dog; we would definitely stay again if the opportunity presents itself."
United States
Stephanie K.
The price is ￥21,979
￥36,877 total
includes taxes & fees
Sep 21 - Sep 22
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

12. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.4 out of 10, Exceptional, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is ￥21,979
￥36,877 total
includes taxes & fees
Sep 21 - Sep 22
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

13. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
The price is ￥30,726
￥63,236 total
includes taxes & fees
Sep 20 - Sep 21
Updated Plymouth Home ~ 5 Mi to Road America!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Sheboygan
10.0 out of 10, Exceptional, (42 reviews)
"Really nice place, everything was perfect! The shower downstairs doesn’t get very hot, but the one upstairs makes up for it. Great location and neighborhood. The garage was a huge help since it dumped 6” of snow while we were there (the owners offering to shovel). The fireplace was really awesome, and my teenage daughter really enjoyed having the entire upstairs to herself. Overall, very happy with our stay."
United States
Kevin K.
The price is ￥26,518
￥71,676 total
includes taxes & fees
Sep 16 - Sep 17
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A dining table with a vase of green leaves and a candle.

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

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Sheboygan
10.0 out of 10, Exceptional, (8 reviews)
"The house was great! It had everything we needed, was very clean, and cozy. We enjoyed our stay and Ginger was welcoming, available, and responsive. "
United States
Christine P.
The price is ￥23,891
￥39,229 total
includes taxes & fees
Sep 21 - Sep 22
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A living room with a sofa, coffee table, and TV.

16. 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
Sheboygan
9.8 out of 10, Exceptional, (35 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥28,656
￥68,122 total
includes taxes & fees
Aug 31 - Sep 1
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A cabin with a deck, a covered porch, and a paved driveway.

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (66 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
The price is ￥31,681
￥43,838 total
includes taxes & fees
Sep 9 - Sep 10
The Esker Ridge Chalet, Pristine Elkhart Solitude
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

18. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
The price is ￥23,562
￥64,831 total
includes taxes & fees
Sep 20 - Sep 21
Updated Plymouth Home ~ 5 Mi to Road America!
A hotel room with two beds, a dining area, and a view of the outdoors.

19. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is ￥17,894
￥31,183 total
includes taxes & fees
Sep 15 - Sep 16
Victorian Inn #241 | 2 Queen Beds
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

20. The Links! - Luxury Golf Retreat with Golf Simulator

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (13 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
The price is ￥35,836
￥97,980 total
includes taxes & fees
Sep 27 - Sep 28
The Links! - Luxury Golf Retreat with Golf Simulator
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 County Hotel Reviews

Siebkens Resort

Siebkens Resort

10/10 Excellent
"We loved the beautiful historic resort. It was very clean, well maintained & all the staff was very nice."
Jody 1-night trip
Posted 19 hours ago
Siebkens Resort

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Vacation Apartments in Sheboygan County

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