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

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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Sheboygan holiday 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, (1,105 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$942
HK$1,069 total
includes taxes & fees
1 Nov - 2 Nov
Grandstay Residential Suites Hotel - Sheboygan
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.

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
10.0 out of 10, Exceptional, (32 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is HK$798
HK$2,046 total
includes taxes & fees
14 Oct - 15 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A bedroom with a wooden headboard, a bed with grey bedding, a fireplace, and a clock displaying 6:00.

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

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Ellis Historical District
9.4 out of 10, Exceptional, (37 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is HK$510
HK$757 total
includes taxes & fees
14 Oct - 15 Oct
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A balcony with a wooden deck, a television on a wooden stand, and a fireplace.

4. Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!

Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Every detail was thought of and the host went out above and beyond to make it a memorable stay. "
United States
Melissa D.
The price is HK$1,452
HK$2,645 total
includes taxes & fees
1 Nov - 2 Nov
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
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
The price is HK$746
HK$1,514 total
includes taxes & fees
9 Nov - 10 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

6. 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, (147 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is HK$1,099
HK$1,325 total
includes taxes & fees
9 Nov - 10 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A living room with a sofa, coffee table, and TV.

7. 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, (42 reviews)
"House is comfortable and clean. Theresa responded quickly to my questions. Excellent location."
United States
Karen K.
The price is HK$2,472
HK$4,739 total
includes taxes & fees
12 Oct - 13 Oct
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

8. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (31 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
The price is HK$1,040
HK$3,167 total
includes taxes & fees
11 Nov - 12 Nov
Sleeps 8 & Spacious!
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

9. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (22 reviews)
"Wonderful property! Communication was wonderful and so very helpful at all times. Not far from the marina, where we spent a lot of our time. "
United States
Susan G.
The price is HK$1,049
HK$2,883 total
includes taxes & fees
9 Nov - 10 Nov
Beautiful & Convenient!
A deck with a view of a lake, surrounded by various signs and advertisements.

10. 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 HK$1,272
HK$5,436 total
includes taxes & fees
12 Oct - 13 Oct
Victorian Inn Elkhart Lake Wisconsin
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

11. 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
The price is HK$950
HK$2,663 total
includes taxes & fees
11 Nov - 12 Nov
Logan Ave Holiday House - Upper
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

12. 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, (13 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is HK$746
HK$1,514 total
includes taxes & fees
8 Nov - 9 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

13. 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 traveller
The price is HK$953
HK$3,069 total
includes taxes & fees
10 Nov - 11 Nov
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

14. 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
10.0 out of 10, Exceptional, (1 review)
"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"
United States
Erin S.
The price is HK$2,072
HK$2,672 total
includes taxes & fees
10 Nov - 11 Nov
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

15. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is HK$3,916
HK$7,624 total
includes taxes & fees
12 Oct - 13 Oct
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A bathroom with white shelves holding wicker baskets and a potted plant.

16. 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.
The price is HK$824
HK$1,612 total
includes taxes & fees
10 Nov - 11 Nov
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (15 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 price is HK$1,766
HK$4,837 total
includes taxes & fees
25 Oct - 26 Oct
The Links! - Luxury Golf Retreat with Golf Simulator
A dining table with a vase of green leaves and a candle.

18. 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.
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Beach

19. 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.
The price is HK$1,530
HK$5,132 total
includes taxes & fees
12 Oct - 13 Oct
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.
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

Home2 Suites By Hilton Sheboygan

Home2 Suites By Hilton Sheboygan

10/10 Excellent
"Breakfast was great. Love the coffee 24/7 is the best."
Scott 2-night trip
Posted 2 hours ago
Home2 Suites By Hilton 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?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This highly rated holiday home rental in Sheboygan 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 holiday with amenities such as a selection of games. Our travellers also rate REMODELED HOME ON LAKE MICHIGAN as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 95 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 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 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.