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

Vacation Rentals in Sheboygan County

Top Cities in Sheboygan County

A lighthouse at sunset with a colorful sky and calm water.
Vacation RentalsVacation Rentals

Sheboygan

Sheboygan

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, (1,131 reviews)
"Was a very nice stay, hotel room was nice and staff was very helpful and friendly. Will definitely be coming back"
United States
Maxim
$102 nightly
The price is $116
Nov 15 - Nov 16
Total with taxes and fees
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
9.4 out of 10, Exceptional, (41 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
$77 nightly
The price is $87
Nov 18 - Nov 19
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A deck with a view of a lake, surrounded by various signs and advertisements.

3. Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin
3.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3 reviews)
"Perfect location, great amenities."
United States
Deirdre
$531 nightly
The price is $578
Nov 15 - Nov 16
Total with taxes and fees
Victorian Inn Elkhart Lake Wisconsin
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.

4. 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
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
$172 nightly
The price is $195
Nov 16 - Nov 17
Total with taxes and fees
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A hallway leading to a room with a wooden floor, a white door, and a painting of sailboats on the wall.

5. 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, (12 reviews)
"Close to everything we were looking to do while visiting the area. Great communication and hospitality from host, would stay again!!"
United States
Heidi
$148 nightly
The price is $168
Nov 15 - Nov 16
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A narrow hallway with a bench, pillows, and a potted plant.

6. 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, (15 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
$157 nightly
The price is $178
Nov 18 - Nov 19
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A bathroom with white shelves holding wicker baskets and a potted plant.

7. 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
9.8 out of 10, Exceptional, (8 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.
$162 nightly
The price is $184
Nov 15 - Nov 16
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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, (23 reviews)
"The place was in a quiet neighborhood and a great location with easy access to everything we needed. Very clean and the host communicated everything clearly."
United States
Susan J.
$293 nightly
The price is $332
Nov 18 - Nov 19
Total with taxes and fees
Beautiful & Convenient!
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

9. 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, (151 reviews)
"Quiet place to just get away."
United States
Cheryl
$131 nightly
The price is $138
Nov 16 - Nov 17
Total with taxes and fees
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.

10. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"Great place in a great location for us."
United States
Dean M.
$333 nightly
The price is $378
Dec 1 - Dec 2
Total with taxes and fees
Sleeps 8 & Spacious!
A modern living room with a sofa, two chairs, a coffee table, a ceiling fan, and a large window with curtains.

11. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great location, centrally located, clean and well-furnished. Ginger was a great host, very accommodating."
United States
Tonja K.
$179 nightly
The price is $203
Nov 16 - Nov 17
Total with taxes and fees
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A view from a room with a sliding glass door to an outdoor deck with a wooden railing.

12. Apartment Centrally Located

Apartment Centrally Located
Plymouth
9.6 out of 10, Exceptional, (5 reviews)
"Room was as advertised, very convenient access to Road America, would stay again"
United States
Dylan C.
$216 nightly
The price is $217
Dec 12 - Dec 13
Total with taxes and fees
Apartment Centrally Located
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

13. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"We had a great time up there and the host was excellent and the property was fantastic"
United States
Alex N.
$298 nightly
The price is $338
Dec 13 - Dec 14
Total with taxes and fees
Logan Ave Holiday House - Upper
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, (43 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.
$318 nightly
The price is $360
Dec 6 - Dec 7
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A deck with a view of a lake, surrounded by various signs and advertisements.

15. 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, (3 reviews)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
$242 nightly
The price is $262
Nov 15 - Nov 16
Total with taxes and fees
First Floor Pet Friendly Queen Suite with Single Pull-out
A resort with a pool, beach, and multiple buildings surrounded by trees.

16. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
$153 nightly
The price is $173
Nov 13 - Nov 14
Total with taxes and fees
Victorian Inn #241 | 2 Queen Beds
A spacious living room with a sofa, coffee table, and a TV. There is a ceiling fan, a fireplace, and a large window.

17. The Beach town bungalow

The Beach town bungalow
Sheboygan
$255 nightly
The price is $257
Nov 13 - Nov 14
Total with taxes and fees
The Beach town bungalow
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.

18. 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, (33 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A cabin with a deck, a covered porch, and a paved driveway.

19. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
$286 nightly
The price is $302
Nov 17 - Nov 18
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
A beach with clear turquoise water, people kayaking, and beach chairs lined up along the shore.

20. Beautifully Updated Two Queen Suite

Beautifully Updated Two Queen Suite
Elkhart Lake
9.6 out of 10, Exceptional, (4 reviews)
"Center located and great access to pools beach etc….dog also had a blast!"
United States
John M.
$242 nightly
The price is $262
Nov 13 - Nov 14
Total with taxes and fees
Beautifully Updated Two Queen Suite
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"Was a very nice stay, hotel room was nice and staff was very helpful and friendly. Will definitely be coming back"
Maxim 1-night trip
Posted 7 hours ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan County

Discover your perfect Sheboygan County vacation rental with Expedia

How many vacation rentals are available in Sheboygan County?


Expedia has plenty of vacation rentals to choose from in and around  Sheboygan County, so you’re guaranteed to find the right one for you. 


How much is a vacation rental in Sheboygan County?


The selection of Sheboygan County vacation rentals we have selected for you start as low as $116 per night. Entering your travel dates in the search wizard you might find even better deals!


What type of vacation rental can I get in Sheboygan County?


Vacation rentals in Sheboygan County come in all shapes and sizes, and your options depend on your chosen travel dates. You could entertain in a blissful vacation home, chill in a private apartment, or find family fun at a resort. Expedia offers a superb choice of Sheboygan County vacation rentals to suit everyone. 


Why should I choose a vacation rental in Sheboygan County?


Expedia’s vacation rentals provide cozy comforts you can sink into on your own schedule. You’ll enjoy your own space in a property with a kitchen, a pool, a garden etc. Maybe you’ll prefer somewhere with a spa or kids activities. A Sheboygan County vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in. 


How do I find the best deal on a vacation rental in Sheboygan County?


Find vacation rentals in Sheboygan County by viewing Expedia’s latest deals, or enter your travel dates and use the filters to select by amenities, price, or rating. Dive into the reviews to get a true feeling of which is your favorite vacation rental in Sheboygan County.  


What amenities are available in a vacation rental in Sheboygan County?


The choice is yours! Perhaps you love cooking in a well-equipped kitchen. Or maybe a late breakfast and a swimming pool is more your thing. Of course, there’s always the treat of having your own hot tub. Expedia has a vast range of amenities in Sheboygan County vacation rentals designed to suit every budget and trip type.


When is the best time to stay in a vacation rental in Sheboygan County?   


Everytime is a great time to head to Sheboygan County! Staying in a Sheboygan County vacation rentals you will always find lots going on to keep you entertained. 


Why book a vacation rental with Expedia?


Expedia has locked in amazing deals on a huge selection of impressive vacation rentals in Sheboygan County. We give you the information and inspiration you need all in one place. With so many properties to choose from, you know you can book your perfect Sheboygan County vacation rental with confidence. ANd don’t forget, if you bundle with a flight or a car rental in Sheboygan County, you can save even more.


Can I cancel my vacation rental through Expedia?  


Yes, you can cancel or change your Sheboygan County vacation rental by contacting your property manager directly. Contact details are easy to find on your itinerary in Trips. For more information, check out our Customer Service Portal and we’ll help you get everything sorted.