A red lighthouse amidst rough seas with waves crashing against a pier.

Sheboygan Vacation Rentals

Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Sheboygan 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, (1,130 reviews)
"Quiet place near the lake."
United States
Vivian
$93 nightly
The price is $106
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
$76 nightly
The price is $86
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
4.0 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 11 - Nov 12
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.
$157 nightly
The price is $178
Nov 27 - Nov 28
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
$149 nightly
The price is $169
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.
$153 nightly
The price is $174
Nov 18 - Nov 19
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

7. 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 bathroom with white shelves holding wicker baskets and a potted plant.

8. 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 11 - Nov 12
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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.

9. 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.
$333 nightly
The price is $378
Nov 11 - Nov 12
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A modern living room with a sofa, two chairs, a coffee table, a ceiling fan, and a large 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
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.
$173 nightly
The price is $196
Nov 11 - Nov 12
Total with taxes and fees
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

11. 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.
$316 nightly
The price is $359
Nov 11 - Nov 12
Total with taxes and fees
Sleeps 8 & Spacious!
A resort with a pool, beach, and multiple buildings surrounded by trees.

12. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
$153 nightly
The price is $173
Nov 11 - Nov 12
Total with taxes and fees
Victorian Inn #241 | 2 Queen Beds
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

13. 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.
$289 nightly
The price is $328
Nov 18 - Nov 19
Total with taxes and fees
Beautiful & Convenient!
A spacious living room with a sofa, coffee table, and a TV. There is a ceiling fan, a fireplace, and a large window.

14. The Beach town bungalow

The Beach town bungalow
Sheboygan
$248 nightly
The price is $249
Nov 13 - Nov 14
Total with taxes and fees
The Beach town bungalow
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. 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.
$314 nightly
The price is $356
Dec 6 - Dec 7
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A view from a room with a sliding glass door to an outdoor deck with a wooden railing.

16. 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.
$179 nightly
The price is $180
Dec 2 - Dec 3
Total with taxes and fees
Apartment Centrally Located
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, (73 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
$242 nightly
The price is $255
Nov 11 - Nov 12
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
A deck with a view of a lake, surrounded by various signs and advertisements.

18. 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 12 - Nov 13
Total with taxes and fees
First Floor Pet Friendly Queen Suite with Single Pull-out
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

19. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (30 reviews)
"Clean , quiet, great host. Property had everything we needed for a two day stay."
United States
Tim C.
$191 nightly
The price is $217
Nov 11 - Nov 12
Total with taxes and fees
2nd floor loft near the lake!
Beach

20. 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.
$547 nightly
The price is $621
Nov 11 - Nov 12
Total with taxes and fees
Beachfront Paradise: King Suite - Sleeps 8!
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 Hotel Reviews

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

10/10 Excellent
"The parking situation was definitely a bit confusing when I first arrived. But maybe that’s because I live out in the country and get confused by downtown areas in general lol! The front desk attendant was helpful and kind in getting everything explained to me. The property was clean, quiet, and I was impressed by all of the amenities included for the price. I leave for work before breakfast hours so was not able to take advantage of that. Would definitely stay again in the future."
Matthew 2-night trip
Posted 1 hour ago
Grandstay Residential Suites Hotel - Sheboygan

Find out more about Sheboygan

Everything you need to know about Sheboygan 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 vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sheboygan vacation rentals: An excellent choice for every season

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $106 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to John Michael Kohler Arts Center, or you can go with a more remote option if you want a relaxing stay. Visitors to Sheboygan speak positively about the scenic lakeside and top-notch restaurants in this destination. Leave some time to check out the marina and museums during your trip.

What are some of the best vacation home rentals in Sheboygan?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You and your friends and family can relax into your vacation with amenities like a selection of games. Our travelers also rate REMODELED HOME ON LAKE MICHIGAN as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 95 Expedia vacation rentals in Sheboygan for a memorable vacation.

What’s there to see and do in Sheboygan?

Enjoy the outdoors at Lake Michigan and Bookworm Gardens, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Stefanie H. Weill Center for the Performing Arts and Blue Harbor Resort & Conference Center Water Park are other places worth a visit.

What’s a vacation rental in Sheboygan like?

A vacation rental is a private property where you can stay for a long or short time in Sheboygan. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.