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
28 Aug - 30 Aug
In two months
9 Oct - 11 Oct
In three months
6 Nov - 8 Nov
In four months
4 Dec - 6 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, (1,069 reviews)
"Great place to stay breakfast was good then room was good. Staff were great as well only issue is the pool is tiny."
United States
Devin
The price is NZ$236
includes taxes & fees
16 Aug - 17 Aug
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, (30 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
The price is NZ$222
includes taxes & fees
17 Aug - 18 Aug
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Dining

3. 4 Bedroom Home on the River with Private River access

4 Bedroom Home on the River with Private River access
Sheboygan
9.8 out of 10, Exceptional, (44 reviews)
"If you are looking for a quiet and calm place to enjoy your morning coffee or watch a sunset, this is the perfect place!"
United States
Sharon R.
4 Bedroom Home on the River with Private River access
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 NZ$360
includes taxes & fees
1 Sept - 2 Sept
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Dining

5. 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 NZ$467
includes taxes & fees
8 Sept - 9 Sept
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Smart TV

6. 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 NZ$461
includes taxes & fees
17 Aug - 18 Aug
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Interior

7. 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 NZ$690
includes taxes & fees
16 Aug - 17 Aug
Sheboygan Riverside Condo
Interior

8. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is NZ$631
includes taxes & fees
19 Aug - 20 Aug
Sleeps 8 & Spacious!
Smart TV

9. 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, (34 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is NZ$722
includes taxes & fees
17 Aug - 18 Aug
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Children’s area

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, (140 reviews)
"Great little cottage. Perfect for a night away "
United States
James R.
The price is NZ$324
includes taxes & fees
1 Sept - 2 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

11. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (6 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is NZ$626
includes taxes & fees
2 Sept - 3 Sept
Logan Ave Holiday House - Upper
TV

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

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, the area is safe and close to the Marina. Owner/host was excellent to communicate with."
United States
Mary A.
The price is NZ$714
includes taxes & fees
17 Aug - 18 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Exterior

13. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.0 out of 10, Very good, (6 reviews)
"The condo was very clean and comfortable. It was just steps from the lake. It's a great place to stay!"
United States
Erika M.
The price is NZ$1,877
includes taxes & fees
24 Aug - 25 Aug
Just Beachy: 4 Bedroom, Sleeps 12!
3 bedrooms, desk, iron/ironing board, travel cot

14. 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 NZ$392
includes taxes & fees
19 Aug - 20 Aug
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV, books

15. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (21 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
The price is NZ$554
includes taxes & fees
31 Aug - 1 Sept
Beautiful & Convenient!
Dining

16. 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 NZ$502
includes taxes & fees
1 Sept - 2 Sept
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Interior

17. 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 NZ$395
includes taxes & fees
13 Sept - 14 Sept
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
House (2 Bedrooms) | Interior

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

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is NZ$706
includes taxes & fees
17 Aug - 18 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Terrace/patio

19. Stunning private home hidden in the woods. Can sleep 11 guests

Stunning private home hidden in the woods. Can sleep 11 guests
Plymouth
10.0 out of 10, Exceptional, (20 reviews)
"Our stay was great! Really enjoyed it!"
United States
Nic B.
The price is NZ$1,629
includes taxes & fees
17 Aug - 18 Aug
Stunning private home hidden in the woods. Can sleep 11 guests
TV

20. The Beach town bungalow

The Beach town bungalow
Sheboygan
The price is NZ$672
includes taxes & fees
12 Sept - 13 Sept
The Beach town bungalow
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

Beach front luxury spacious villa !

Beach front luxury spacious villa !

10/10 Excellent
"Very nice upscale villa on the lake. Everything was as advertised. Communication was excellent."
Todd S. 2-night trip
Posted 1 hour ago
Beach front luxury spacious villa !

Find out more about Sheboygan

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Sheboygan holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Sheboygan. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Sheboygan. Seeing all the best attractions is bound to make you fall in love with Sheboygan. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Sheboygan short-term rentals, that won’t be hard to do.

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. Some other homes for rent in Sheboygan include Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! and Lake Michigan Home with gorgeous views, great spot for family or golf retreat.

How many holiday rentals will I find in Sheboygan?

Choose from 96 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.