Sheboygan County Holiday Rentals

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Our top choices for Sheboygan County holiday rentals

Bar (on property)

Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
The price is HK$952
HK$5,022 total
includes taxes & fees
15 Apr - 16 Apr
Victorian Inn Elkhart Lake Wisconsin
Lobby

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,027 reviews)
"Room was clean, staff was nice. The breakfast was pretty darn good. "
United States
andrea
The price is HK$1,189
HK$1,350 total
includes taxes & fees
13 Apr - 14 Apr
Grandstay Residential Suites Hotel - Sheboygan
Smart TV

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown

3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Sheboygan
10.0 out of 10, Exceptional, (14 reviews)
"Very nice,had everything you need. Nicely decorated.. close to town and parks"
United States
Dennis B.
The price is HK$619
HK$1,280 total
includes taxes & fees
13 Apr - 14 Apr
3 Blocks from lake walk to Lake, guest house 1 BDRM full bath 4 min to downtown
Dining

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, (13 reviews)
"Super cute place with great amenities. I even got to park my car in the garage! We enjoyed our stay here!"
United States
Carolyn W.
The price is HK$744
HK$1,920 total
includes taxes & fees
4 May - 5 May
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Children’s area

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, (126 reviews)
"Welcoming and accommodating host, very clean and cozy cottage, amazing fireplace "
United States
Cade R.
The price is HK$987
HK$1,206 total
includes taxes & fees
16 Apr - 17 Apr
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Bar (on property)

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 reviews)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
The price is HK$1,804
HK$3,035 total
includes taxes & fees
13 Apr - 14 Apr
First Floor Pet Friendly Queen Suite with Single Pull-out
Interior

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 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 HK$893
HK$1,547 total
includes taxes & fees
13 Apr - 14 Apr
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
3 bedrooms, desk, iron/ironing board, travel cot

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, (11 reviews)
"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 HK$846
HK$1,493 total
includes taxes & fees
19 Apr - 20 Apr
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
1 bedroom, WiFi

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, (25 reviews)
"Great place! Nice location and very comfortable. "
United States
Jana F.
The price is HK$744
HK$1,022 total
includes taxes & fees
15 Apr - 16 Apr
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Interior

*NEW* Sleeps 8 & Spacious!

*NEW* Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is HK$861
HK$2,924 total
includes taxes & fees
13 Apr - 14 Apr
*NEW* Sleeps 8 & Spacious!
Front of property

Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
The price is HK$1,261
HK$3,060 total
includes taxes & fees
13 Apr - 14 Apr
Modern South Pier Condo on Sheboygan River!
Living area

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.
Ellis Historical District
9.6 out of 10, Exceptional, (12 reviews)
"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 HK$901
HK$1,200 total
includes taxes & fees
14 Apr - 15 Apr
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Fridge, microwave, oven, stovetop

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, (41 reviews)
"We absolutely loved our stay. Everything was so well stocked and comfortable. Perfect location near the lake. Between the fenced in yard for the dog and the little play area for the kids, it couldn’t have worked out better."
United States
Jean S.
The price is HK$940
HK$3,049 total
includes taxes & fees
13 Apr - 14 Apr
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (59 reviews)
"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 HK$1,558
HK$2,131 total
includes taxes & fees
12 May - 13 May
The Esker Ridge Chalet, Pristine Elkhart Solitude
3 bedrooms, iron/ironing board, travel cot, WiFi

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 review)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
The price is HK$803
HK$1,445 total
includes taxes & fees
13 Apr - 14 Apr
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Interior

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth

Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Plymouth
9.6 out of 10, Exceptional, (10 reviews)
"Great property! Close to many great places. Property was very kid and adult friendly. Great time with family. We'll be back again. "
United States
Andrew M.
The price is HK$1,501
HK$4,467 total
includes taxes & fees
13 Apr - 14 Apr
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
Smart TV, books

*NEW* Beautiful & Convenient!

*NEW* Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (20 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is HK$896
HK$2,679 total
includes taxes & fees
13 Apr - 14 Apr
*NEW* Beautiful & Convenient!
Exterior

Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (4 reviews)
"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 HK$1,182
HK$2,960 total
includes taxes & fees
12 May - 13 May
Logan Ave Holiday House - Upper
TV

The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is HK$799
HK$1,608 total
includes taxes & fees
30 Apr - 1 May
The Beach town bungalow
Dining

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, (6 reviews)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
United States
Stacy P.
The price is HK$1,057
HK$1,760 total
includes taxes & fees
19 Apr - 20 Apr
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Very clean and ascetically pleasing "
Cynthia 2-night trip
Posted 1 hour ago
Watershed Hotel