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Holiday Rentals in Sheboygan County

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Our top choices for Sheboygan County holiday rentals

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Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1013)
"Would definitely stay here again!"
United States
Donna
The price is €120
includes taxes & fees
28 Dec - 29 Dec
Grandstay Residential Suites Hotel - Sheboygan
Luxury Condo | Terrace/patio
Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin
Bar (on property)
First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out

First Floor Pet Friendly Queen Suite with Single Pull-out
Elkhart Lake
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is €254
includes taxes & fees
31 Dec - 1 Jan 2026
First Floor Pet Friendly Queen Suite with Single Pull-out
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.8 out of 10, Exceptional, (24)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is €115
includes taxes & fees
29 Dec - 30 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Smart TV, books, music library
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!

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Downtown Sheboygan
9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is €217
includes taxes & fees
11 Jan - 12 Jan 2026
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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.

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Oostburg
10.0 out of 10, Exceptional, (116)
"We loved the cozy cottage and cuddled up with books under the afghans on the cool evenings. The lake was a pleasant walk away."
United States
bev w.
The price is €129
includes taxes & fees
5 Jan - 6 Jan 2026
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
3 bedrooms, iron/ironing board, WiFi, bed sheets
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

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Sheboygan
10.0 out of 10, Exceptional, (4)
"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 €148
includes taxes & fees
11 Jan - 12 Jan 2026
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
House (2 Bedrooms) | Interior
Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is €342
includes taxes & fees
28 Dec - 29 Dec
Large Backyard, Walk to Hospital: Sheboygan Abode!
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.

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
2.0 star property
Ellis Historical District
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.
The price is €134
includes taxes & fees
28 Dec - 29 Dec
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Property grounds
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
2.0 star property
Sheboygan
10.0 out of 10, Exceptional, (7)
The price is €245
includes taxes & fees
29 Dec - 30 Dec
NEW Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.2 out of 10, Wonderful, (10)
"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. "
United States
Kim K.
The price is €140
includes taxes & fees
4 Jan - 5 Jan 2026
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Fridge, microwave, oven, stovetop
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Sheboygan
9.8 out of 10, Exceptional, (255)
"Beautiful view and perfect for our Wisconsin lake getaway."
United States
Holly A.
The price is €273
includes taxes & fees
31 Dec - 1 Jan 2026
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Indoor pool, a heated pool
Modern Room Near Indoor Pool

Modern Room Near Indoor Pool

Modern Room Near Indoor Pool
Elkhart Lake
9.6 out of 10, Exceptional, (4)
"Our host was extremely responsive and resourceful. The room was very clean and nice. "
United Kingdom
Brandon B.
The price is €238
includes taxes & fees
31 Dec - 1 Jan 2026
Modern Room Near Indoor Pool
Exterior
The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (58)
"Great spot, super close to town (and the always great Off The Rail cafe). Clean and quiet. Used as a base for track time at Road America."
United States
Scott G.
The price is €236
includes taxes & fees
31 Dec - 1 Jan 2026
The Esker Ridge Chalet, Pristine Elkhart Solitude
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

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Sheboygan
10.0 out of 10, Exceptional, (21)
"Wonderfully close to the lake. Sad there was no off street parking."
United States
Lucas T.
The price is €347
includes taxes & fees
4 Jan - 5 Jan 2026
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Fridge, microwave, oven, stovetop
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

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, (39)
"Very clean, cute, great communication, location & walkability! "
United States
Sandee M.
The price is €345
includes taxes & fees
13 Jan - 14 Jan 2026
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Exterior detail
Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (3)
"We had a great stay here during the boat races. The host was so nice and left us local cheese & beer to welcome us to the house/city. We would definitely stay here again!"
United States
MELISSA C.
The price is €256
includes taxes & fees
4 Jan - 5 Jan 2026
Logan Ave Holiday House - Upper
Property grounds
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

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
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is €140
includes taxes & fees
4 Jan - 5 Jan 2026
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Smart TV, books
*NEW* Beautiful & Convenient!

*NEW* Beautiful & Convenient!

*NEW* Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (19)
"The place was perfect for our family! Clean, 3 bedrooms, nicely furnished and equipped. The hosts were terrific. Provided all the info and were very responsive. 1st rate experience!"
United States
Todd S.
The price is €292
includes taxes & fees
13 Jan - 14 Jan 2026
*NEW* Beautiful & Convenient!
Indoor pool, a heated pool
Upscale Waterfront and Pool View Condo!!

Upscale Waterfront and Pool View Condo!!

Upscale Waterfront and Pool View Condo!!
Elkhart Lake
10.0 out of 10, Exceptional, (4)
"We were in town for activities at Road America. The location of this villa is ideal and only a couple of miles from the track"
United States
Jason A.
Upscale Waterfront and Pool View Condo!!
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

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

10/10 Excellent
"Staff professional and respectful. Rooms clean, quiet and comfortable. Check in and out easy. Location convenient. Recommend "
Lisa 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Sheboygan

Find out more about Sheboygan County

Holiday Homes in Sheboygan County

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