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

Sheboygan County Vacation Rentals

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Top Cities in Sheboygan County

A lighthouse at sunset with a colorful sky and calm water.
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Sheboygan

Sheboygan
A house by a calm lake with autumn foliage and a clear sky.
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Elkhart Lake

Elkhart Lake

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, (1,100 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is CA $171
CA $194 total
includes taxes & fees
Nov 1 - Nov 2
Grandstay Residential Suites Hotel - 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.

2. 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, (32 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is CA $145
CA $373 total
includes taxes & fees
Oct 14 - Oct 15
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A fire pit surrounded by four light blue chairs in a grassy outdoor area.

3. 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, (10 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
The price is CA $135
CA $275 total
includes taxes & fees
Nov 2 - Nov 3
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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
9.8 out of 10, Exceptional, (19 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is CA $114
CA $259 total
includes taxes & fees
Oct 6 - Oct 7
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A balcony with a wooden deck, a television on a wooden stand, and a fireplace.

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

Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Every detail was thought of and the host went out above and beyond to make it a memorable stay. "
United States
Melissa D.
The price is CA $264
CA $480 total
includes taxes & fees
Nov 1 - Nov 2
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

6. 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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is CA $205
CA $247 total
includes taxes & fees
Oct 7 - Oct 8
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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.
The price is CA $135
CA $275 total
includes taxes & fees
Oct 7 - Oct 8
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A deck with a view of a lake, surrounded by various signs and advertisements.

8. 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 CA $231
CA $987 total
includes taxes & fees
Oct 11 - Oct 12
Victorian Inn Elkhart Lake Wisconsin
A dining table with a vase of green leaves and a candle.

9. 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 CA $178
CA $340 total
includes taxes & fees
Nov 1 - Nov 2
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A dining area with a table, chairs, and a window with curtains.

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
The price is CA $214
CA $374 total
includes taxes & fees
Nov 3 - Nov 4
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

11. 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, (13 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is CA $171
CA $322 total
includes taxes & fees
Nov 2 - Nov 3
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

12. 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)
"Many extras that we have never seen at other rentals.Children's toys, beach toys, dog extras- leash dog bowls towels and a new toy to bring home. Walking distance to Lake Michigan. Restaurants that are 5 min distance driving. Kohler Andrae 15 min away! Kitchen had every item you would need.Hope to say again. Thanks for a great experience"
United States
Anonymous traveller
The price is CA $192
CA $581 total
includes taxes & fees
Nov 2 - Nov 3
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A cabin with a deck, a covered porch, and a paved driveway.

13. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (71 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 CA $284
CA $389 total
includes taxes & fees
Oct 6 - Oct 7
The Esker Ridge Chalet, Pristine Elkhart Solitude
Beach

14. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 reviews)
"It was ok but it was the second year in a row that we did not get condo we rented due to a "door lock" issue."
United States
Nina S.
The price is CA $278
CA $922 total
includes taxes & fees
Oct 6 - Oct 7
Beachfront Paradise: King Suite - Sleeps 8!
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (14 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 CA $321
CA $878 total
includes taxes & fees
Nov 1 - Nov 2
The Links! - Luxury Golf Retreat with Golf Simulator
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

16. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"
United States
Erin S.
The price is CA $376
CA $488 total
includes taxes & fees
Oct 6 - Oct 7
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A living room with a sofa, coffee table, and TV.

17. 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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is CA $449
CA $851 total
includes taxes & fees
Oct 6 - Oct 7
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A spacious living area with a modern staircase, a fireplace, and a flat-screen TV mounted on the wall.

18. 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
9.8 out of 10, Exceptional, (18 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 CA $304
CA $855 total
includes taxes & fees
Oct 27 - Oct 28
Charming dome house - 4-bedroom house with WiFi and AC in enjoyable Plymouth
A deck with a view of a lake, surrounded by various signs and advertisements.

19. 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 CA $410
CA $661 total
includes taxes & fees
Oct 12 - Oct 13
First Floor Pet Friendly Queen Suite with Single Pull-out
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)
"Our host was extremely responsive and resourceful. The room was very clean and nice. "
United Kingdom
Brandon B.
The price is CA $410
CA $661 total
includes taxes & fees
Oct 6 - Oct 7
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

8/10 Good
"Location was disappointing. We were driving everywhere for sightseeing and restaurants."
Barbara 2-night trip
Posted 1 hour ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan County

Everything you need to know about Sheboygan County vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan County vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheboygan County vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheboygan County vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan County. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. 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.  The selection of Sheboygan County vacation rentals we have selected for you start as low as CA $194 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheboygan County rentals

At Expedia, we put the best Sheboygan County vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Sheboygan County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheboygan County vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheboygan County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.