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

Sheboygan Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Sheboygan holiday 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, (1,073 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$995
HK$1,130 total
includes taxes & fees
16 Sept - 17 Sept
Grandstay Residential Suites Hotel - Sheboygan
1 bedroom, WiFi

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, (31 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is HK$744
HK$1,023 total
includes taxes & fees
31 Aug - 1 Sept
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Dining

3. 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, (24 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is HK$825
HK$2,093 total
includes taxes & fees
8 Sept - 9 Sept
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
3 bedrooms, iron/ironing board, travel cot, WiFi

4. 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, (9 reviews)
"We enjoyed our stay and found the place very comfortable for our family of five. It was easy to walk down to see the lake and a quick drive to restaurants in town."
United States
Amanda
The price is HK$804
HK$1,455 total
includes taxes & fees
1 Sept - 2 Sept
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Interior

5. 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 HK$862
HK$2,926 total
includes taxes & fees
31 Aug - 1 Sept
Sleeps 8 & Spacious!
Exterior

6. 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 HK$875
HK$2,559 total
includes taxes & fees
2 Sept - 3 Sept
Logan Ave Holiday House - Upper
Smart TV, books

7. 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 HK$862
HK$2,633 total
includes taxes & fees
31 Aug - 1 Sept
Beautiful & Convenient!
Children’s area

8. 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, (140 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is HK$1,129
HK$1,364 total
includes taxes & fees
1 Sept - 2 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Smart TV

9. 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, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
The price is HK$1,175
HK$2,135 total
includes taxes & fees
31 Aug - 1 Sept
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Coffee/tea maker, fridge, microwave, oven

10. 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 HK$1,234
HK$3,429 total
includes taxes & fees
16 Sept - 17 Sept
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
3 bedrooms, desk, iron/ironing board, travel cot

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.
The price is HK$1,082
HK$1,815 total
includes taxes & fees
21 Sept - 22 Sept
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV

12. 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, (35 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is HK$1,411
HK$3,353 total
includes taxes & fees
27 Aug - 28 Aug
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Interior

13. 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, (6 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 HK$1,128
HK$1,877 total
includes taxes & fees
8 Sept - 9 Sept
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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 HK$1,058
HK$1,779 total
includes taxes & fees
1 Sept - 2 Sept
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Interior

15. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
The price is HK$2,092
HK$3,068 total
includes taxes & fees
31 Aug - 1 Sept
Sheboygan Riverside Condo
Interior

16. 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 HK$1,513
HK$3,113 total
includes taxes & fees
20 Sept - 21 Sept
Updated Plymouth Home ~ 5 Mi to Road America!
Living area

17. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (24 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.
The price is HK$1,037
HK$1,808 total
includes taxes & fees
30 Aug - 31 Aug
2nd floor loft near the lake!
3 bedrooms, iron/ironing board, WiFi, bed sheets

18. 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 HK$2,069
HK$2,686 total
includes taxes & fees
1 Sept - 2 Sept
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Exterior

19. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (66 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 HK$1,559
HK$2,158 total
includes taxes & fees
2 Sept - 3 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude
Coffee/tea maker, fridge, microwave, stovetop

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

Updated Plymouth Home ~ 5 Mi to Road America!
Plymouth
10.0 out of 10, Exceptional, (19 reviews)
"This house was an excellent choice for our race weekend at Road America. It was very clean, the bedrooms were comfortable, check-in was easy, the neighborhood was quiet, and the proximity to the race track was great. Would definitely stay again!"
United States
Patricia V.
The price is HK$1,160
HK$3,192 total
includes taxes & fees
20 Sept - 21 Sept
Updated Plymouth Home ~ 5 Mi to Road America!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheboygan Hotel Reviews

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

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

10/10 Excellent
"Great area! Easy to park right in front. Super quick communication. Everything I needed in this cute place."
Rachel 3-night trip
Posted 9 hours ago
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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:

  • View our selection of featured holiday rentals in Sheboygan
  • Use the map to find apartments and other holiday homes in the Sheboygan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheboygan while they last

Look no further and take a look at our great range of rental properties in Sheboygan!

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to John Michael Kohler Arts Center, or you can select a more secluded option if you're looking for 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 holiday rentals that Sheboygan has to offer?

REMODELED HOME ON LAKE MICHIGAN: This highly rated holiday home rental in Sheboygan is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Make the most of games in this rental home to help you unwind. Our travellers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 94 Expedia holiday rentals in Sheboygan for a memorable holiday.

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, 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 holiday rental in Sheboygan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheboygan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.