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Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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, (1,095 reviews)
"Nice place and good breakfast"
United States
Kristin
$140 nightly
The price is $159
Oct 4 - Oct 5
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
9.6 out of 10, Exceptional, (33 reviews)
"The room was very clean and, as described. It was perfect for our weekend event. It was easy to communicate with the host."
United States
Kimberly H.
$115 nightly
The price is $131
Oct 4 - Oct 5
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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.

3. 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.
$160 nightly
The price is $182
Oct 6 - Oct 7
Total with taxes and fees
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
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.

4. 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, (31 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$230 nightly
The price is $261
Oct 14 - Oct 15
Total with taxes and fees
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.

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, (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
$165 nightly
The price is $187
Oct 6 - Oct 7
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A deck with a view of a lake, surrounded by various signs and advertisements.

6. 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
$644 nightly
The price is $706
Oct 4 - Oct 5
Total with taxes and fees
Victorian Inn Elkhart Lake Wisconsin
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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
$164 nightly
The price is $173
Oct 7 - Oct 8
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

8. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.4 out of 10, Exceptional, (9 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
$284 nightly
The price is $322
Oct 20 - Oct 21
Total with taxes and fees
Logan Ave Holiday House - Upper
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

9. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (30 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
$331 nightly
The price is $376
Oct 6 - Oct 7
Total with taxes and fees
Sleeps 8 & Spacious!
A bathroom with white shelves holding wicker baskets and a potted plant.

10. 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, (7 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.
$176 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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, (12 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
$171 nightly
The price is $194
Oct 7 - Oct 8
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern living room with a ceiling fan, two sofas, a coffee table, and a TV.

12. Close to Downtown & Shore | Great Location

Close to Downtown & Shore | Great Location
Sheboygan
9.0 out of 10, Wonderful, (10 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
$299 nightly
The price is $339
Oct 4 - Oct 5
Total with taxes and fees
Close to Downtown & Shore | Great Location
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, (22 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
$296 nightly
The price is $336
Oct 6 - Oct 7
Total with taxes and fees
Beautiful & Convenient!
A dining table with a vase of green leaves and a candle.

14. 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.
$222 nightly
The price is $252
Oct 20 - Oct 21
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A dining area with a table, chairs, and a window with curtains.

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

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
$228 nightly
The price is $259
Nov 1 - Nov 2
Total with taxes and fees
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

16. 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 traveler
$376 nightly
The price is $426
Oct 20 - Oct 21
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
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, (70 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
$258 nightly
The price is $272
Oct 6 - Oct 7
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

18. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (28 reviews)
"The location was amazing and the place is really nice! Absolutely love that it is dog friendly and the host is really responsive! We will definitely be staying again! "
United States
Emily G.
$200 nightly
The price is $227
Oct 4 - Oct 5
Total with taxes and fees
2nd floor loft near the lake!
Beach

19. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
6.8 out of 10, (5 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.
$572 nightly
The price is $649
Oct 2 - Oct 3
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

Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan

10/10 Excellent
"The staff was so kind and helpful the whole time. I do have to say the two things that bothered me, the iron was broken so I had to use someone elses to get my outfit for a conference ready. And I got dinner from texas roadhouse, I opened the drawer to use the steak knife and it was really gross. The cover hadn't been cleaned from the last person who used it."
Alyxandreah 2-night trip
Posted 14 hours ago
Home2 Suites By Hilton 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 $131 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.