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

Sheboygan Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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, (1,111 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is AU$194
includes taxes & fees
1 Nov - 2 Nov
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
9.4 out of 10, Exceptional, (38 reviews)
"Very quiet, and only two blocks from Lake Michigan"
United States
Terri
The price is AU$140
includes taxes & fees
12 Nov - 13 Nov
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
A fire pit surrounded by four light blue chairs in a grassy outdoor area.

3. 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 AU$279
includes taxes & fees
9 Nov - 10 Nov
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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, (32 reviews)
"The location was perfect to experience the Art Fair, downtown, and the area overall!Clean & comfortable - would return!"
United States
Andrea L.
The price is AU$425
includes taxes & fees
25 Oct - 26 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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.

5. 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
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is AU$391
includes taxes & fees
31 Oct - 1 Nov
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
A balcony with a wooden deck, a television on a wooden stand, and a fireplace.

6. 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, (18 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 AU$447
includes taxes & fees
1 Nov - 2 Nov
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
A bathroom with white shelves holding wicker baskets and a potted plant.

7. 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 AU$311
includes taxes & fees
27 Oct - 28 Oct
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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
The price is AU$465
includes taxes & fees
18 Nov - 19 Nov
Logan Ave Holiday House - Upper
A dining table with a vase of green leaves and a candle.

9. 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)
"We stayed a very short time due to many wedding details and festivities and the stay was just what we needed. Convenient to wedding location, very clean, comfy beds, friendly and reliable host! Would highly recommend!"
United States
Stephanie M.
The price is AU$329
includes taxes & fees
22 Oct - 23 Oct
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

10. 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, (149 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is AU$244
includes taxes & fees
17 Nov - 18 Nov
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A dining area with a table, chairs, and a window with curtains.

11. 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 AU$319
includes taxes & fees
17 Nov - 18 Nov
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

12. 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 AU$471
includes taxes & fees
22 Oct - 23 Oct
Beautiful & Convenient!
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

13. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (32 reviews)
"It suited our needs. Interior lighting was a bit harsh"
United States
James
The price is AU$526
includes taxes & fees
27 Oct - 28 Oct
Sleeps 8 & Spacious!
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

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

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Sheboygan
9.6 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
The price is AU$277
includes taxes & fees
3 Nov - 4 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

15. 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.
The price is AU$394
includes taxes & fees
25 Oct - 26 Oct
Sheboygan Riverside Condo
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 traveller
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

17. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (30 reviews)
"Clean , quiet, great host. Property had everything we needed for a two day stay."
United States
Tim C.
The price is AU$329
includes taxes & fees
25 Oct - 26 Oct
2nd floor loft near the lake!
A hotel room with two beds, a dining area, and a view of the outdoors.

18. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is AU$253
includes taxes & fees
30 Oct - 31 Oct
Victorian Inn #241 | 2 Queen Beds
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 AU$913
includes taxes & fees
21 Nov - 22 Nov
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

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent
"The staff was very friendly and the room was clean"
Spencer 3-night trip
Posted 11 hours ago
La Quinta Inn by Wyndham Sheboygan

Find out more about Sheboygan

Everything you need to know about Sheboygan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Sheboygan holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheboygan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheboygan holiday rentals we have selected for you start as low as AU$140 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan holiday 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 holiday.

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. 

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.