Sheboygan Vacation Rentals from $131: Search Short-Term Rentals

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

REMODELED HOME ON LAKE MICHIGAN : This Sheboygan vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favorite home for rent in Sheboygan.

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In two weeks

In two months

In three months

In four months

Our top choices for Sheboygan vacation rentals

1. Grandstay Residential Suites Hotel - Sheboygan

Downtown Sheboygan

Kristin

$123 nightly

Sep 17 - Sep 18

Total with taxes and fees

2. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Ellis Historical District

Hannah T.

$115 nightly

Aug 20 - Aug 21

Total with taxes and fees

3. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Downtown Sheboygan

Zay B.

$235 nightly

Sep 8 - Sep 9

Total with taxes and fees

4. Sleeps 8 & Spacious!

Sheboygan

Beth D.

$329 nightly

Aug 24 - Aug 25

Total with taxes and fees

3 bedrooms, iron/ironing board, travel crib, WiFi

5. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

Sheboygan

Amanda

$176 nightly

Sep 14 - Sep 15

Total with taxes and fees

6. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

Sheboygan

Sylvia L.

$216 nightly

Aug 19 - Aug 20

Total with taxes and fees

7. Beautiful & Convenient!

Sheboygan

stormy a.

$299 nightly

Aug 31 - Sep 1

Total with taxes and fees

8. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

Oostburg

James R.

$165 nightly

Sep 1 - Sep 2

Total with taxes and fees

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Top Sheboygan Hotel Reviews

Comfort Inn & Suites Sheboygan I-43

8/10 Good

"Awesomeness customer service from checking in to checking out. Definitely recommend and will stay again."

Holiday Inn Express Sheboygan-Kohler by IHG

10/10 Excellent

"We initially got a room with a broken and moldy ac but we were moved into another room in less than 5 minutes and it was perfect. Really felt we just got an unlucky draw and they were more than accommodating to make everything right and make sure everything else was perfect."

AmericInn by Wyndham Sheboygan

8/10 Good

"Due to the repairs being made the lobby had a small weird smell. The room was clean and didn't have the smell from the lobby. The breakfast was ok but not really attended well by the staff. The eggs were wierd the bacon and sausage was good. The potatoes also had a weird taste to them. Only one of the 5 days was the food low and running out. over all the staff was freindly, the rooom was great. The parking on the other hand had a few issues. There was some extremly large trucks parking sideways and taking 3 or 4 parking spaces."

Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

10/10 Excellent

"This was a very nice property. Completely met our needs. I provide the following information for the owner: Tips are missing from the cues for the pool table, tips on darts for the electronic dart game need replacement and could not find remote for tv in first floor bedroom. It was very clean and comfortable."

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.

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Things to do in Sheboygan

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?

REMODELED HOME ON LAKE MICHIGAN: This Sheboygan vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 94 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 North Side Municipal Beach, or simply take in cultural attractions like John Michael Kohler Arts Center and Sheboygan County Historical Museum. While here, Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens 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.

Sheboygan Vacation Rentals

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Our top choices for Sheboygan vacation rentals

1. Grandstay Residential Suites Hotel - Sheboygan

2. Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

3. Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

4. Sleeps 8 & Spacious!

5. Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan

6. 3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4

7. Beautiful & Convenient!

8. Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

9. Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10. Logan Ave Holiday House - Upper

11. Large Backyard, Walk to Hospital: Sheboygan Abode!

12. Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city

13. Large Backyard, Walk to Hospital: Sheboygan Abode!

14. Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

15. Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

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

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

18. Updated Plymouth Home ~ 5 Mi to Road America!

19. Sheboygan Riverside Condo

20. Victorian Inn #241 | 2 Queen Beds

Find vacation rentals that suit your style

Top Sheboygan Hotel Reviews

Comfort Inn & Suites Sheboygan I-43

Find out more about Sheboygan

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