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Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Sheboygan vacation rentals

Lobby

1. Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (1,077 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥16,505
￥18,733 total
includes taxes & fees
Sep 27 - Sep 28
Grandstay Residential Suites Hotel - Sheboygan
Dining

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
9.8 out of 10, Exceptional, (29 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is ￥18,101
￥43,793 total
includes taxes & fees
Oct 4 - Oct 5
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Room

3. 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, (32 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is ￥15,084
￥20,725 total
includes taxes & fees
Sep 7 - Sep 8
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Interior

4. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (29 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is ￥18,334
￥60,815 total
includes taxes & fees
Sep 9 - Sep 10
Sleeps 8 & Spacious!
Children's area

5. 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, (141 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥22,864
￥27,472 total
includes taxes & fees
Sep 7 - Sep 8
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Living area

6. 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, (39 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥50,016
￥95,876 total
includes taxes & fees
Sep 7 - Sep 8
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Private kitchen

7. 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 ￥19,033
￥35,967 total
includes taxes & fees
Sep 8 - Sep 9
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Private kitchen

8. 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)
"Really nice place, everything was perfect! The shower downstairs doesn’t get very hot, but the one upstairs makes up for it. Great location and neighborhood. The garage was a huge help since it dumped 6” of snow while we were there (the owners offering to shovel). The fireplace was really awesome, and my teenage daughter really enjoyed having the entire upstairs to herself. Overall, very happy with our stay."
United States
Kevin K.
The price is ￥23,791
￥68,281 total
includes taxes & fees
Sep 30 - Oct 1
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Dining

9. 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 ￥29,216
￥50,281 total
includes taxes & fees
Sep 9 - Sep 10
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Exterior

10. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.6 out of 10, Exceptional, (8 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is ￥20,667
￥56,008 total
includes taxes & fees
Sep 22 - Sep 23
Logan Ave Holiday House - Upper
Living area

11. 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.
The price is ￥19,963
￥56,721 total
includes taxes & fees
Sep 22 - Sep 23
Beautiful & Convenient!
Interior

12. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
Sheboygan Riverside Condo
Living area

13. 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.
Close to Downtown & Shore | Great Location
Dining

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.
The price is ￥32,010
￥53,993 total
includes taxes & fees
Sep 16 - Sep 17
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
House (3 Bedrooms) | Interior

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

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
The price is ￥30,645
￥63,069 total
includes taxes & fees
Sep 20 - Sep 21
Updated Plymouth Home ~ 5 Mi to Road America!
Private kitchen

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (13 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 Links! - Luxury Golf Retreat with Golf Simulator
Room

17. 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
The price is ￥41,918
￥54,425 total
includes taxes & fees
Sep 7 - Sep 8
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Living area

18. The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is ￥43,257
￥64,184 total
includes taxes & fees
Sep 25 - Sep 26
The Beach town bungalow
Bar (on property)

19. 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 ￥25,740
￥109,984 total
includes taxes & fees
Oct 4 - Oct 5
Victorian Inn Elkhart Lake Wisconsin
Exterior

20. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (68 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 ￥31,597
￥43,553 total
includes taxes & fees
Sep 9 - Sep 10
The Esker Ridge Chalet, Pristine Elkhart Solitude
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

Harbor Winds Hotel

Harbor Winds Hotel

10/10 Excellent
"Great location, comfortable beds. Cute little lounge are. Jack the bartender makes a great old fashion."
Karen 1-night trip
Posted 17 hours ago
Harbor Winds Hotel

Find out more about Sheboygan

Search for holiday rentals in Sheboygan on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheboygan using one of the methods below:

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Look no further and take a look at our great range of rental properties 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 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 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.