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Sheboygan Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 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, (1,072 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is HK$941
HK$1,068 total
includes taxes & fees
23 Aug - 24 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 HK$745
HK$1,024 total
includes taxes & fees
21 Aug - 22 Aug
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$918
HK$2,208 total
includes taxes & fees
8 Sept - 9 Sept
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Interior

4. 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 HK$862
HK$2,929 total
includes taxes & fees
24 Aug - 25 Aug
Sleeps 8 & Spacious!
3 bedrooms, iron/ironing board, travel cot, WiFi

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, (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$890
HK$1,562 total
includes taxes & fees
1 Sept - 2 Sept
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
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 HK$1,177
HK$2,137 total
includes taxes & fees
31 Aug - 1 Sept
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Smart TV, books

7. 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 HK$871
HK$2,645 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)
"Great little cottage. Perfect for a night away "
United States
James R.
The price is HK$1,130
HK$1,366 total
includes taxes & fees
1 Sept - 2 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
3 bedrooms, desk, iron/ironing board, travel cot

9. 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$974
HK$1,676 total
includes taxes & fees
20 Aug - 21 Aug
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Exterior

10. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (7 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
The price is HK$1,080
HK$2,829 total
includes taxes & fees
1 Sept - 2 Sept
Logan Ave Holiday House - Upper
Interior

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

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
The price is HK$1,420
HK$3,245 total
includes taxes & fees
20 Aug - 21 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
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, (34 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is HK$1,412
HK$3,356 total
includes taxes & fees
31 Aug - 1 Sept
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
TV

13. 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 HK$1,075
HK$3,330 total
includes taxes & fees
20 Aug - 21 Aug
Large Backyard, Walk to Hospital: Sheboygan Abode!
Interior

14. 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$1,224
HK$1,994 total
includes taxes & fees
20 Aug - 21 Aug
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Dining

15. 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$1,177
HK$1,932 total
includes taxes & fees
14 Sept - 15 Sept
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Coffee/tea maker, fridge, microwave, oven

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (12 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$2,196
HK$5,395 total
includes taxes & fees
23 Aug - 24 Aug
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (65 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$1,561
HK$2,151 total
includes taxes & fees
2 Sept - 3 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude
Coffee/tea maker, fridge, microwave, stovetop

18. 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$1,161
HK$3,194 total
includes taxes & fees
23 Aug - 24 Aug
Updated Plymouth Home ~ 5 Mi to Road America!
Interior

19. 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$1,624
HK$2,529 total
includes taxes & fees
20 Aug - 21 Aug
Sheboygan Riverside Condo
Iron/ironing board, WiFi, bed sheets

20. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is HK$1,066
HK$1,762 total
includes taxes & fees
2 Sept - 3 Sept
Victorian Inn #241 | 2 Queen Beds
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

Comfort Inn & Suites Sheboygan I-43

Comfort Inn & Suites Sheboygan I-43

8/10 Good
"Rocky the front staff person who look like he had to do it all like doing the breakfast, checking in people checking the pool area. He was amazing and so very helpful and kind and understanding."
Gail 1-night trip
Posted 13 hours ago
Comfort Inn & Suites Sheboygan I-43

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
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  • 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, Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens 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.