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

Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Sheboygan vacation 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, (1,096 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is AED 441
AED 500 total
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, (34 reviews)
"The room was very clean and, as described. It was perfect for our weekend event. It was easy to communicate with the host."
United States
Kimberly H.
The price is AED 239
AED 354 total
includes taxes & fees
5 Oct - 6 Oct
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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.

3. 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, (19 reviews)
"Great place to stay and only a short walk to the beautiful beach."
United States
Brian L.
The price is AED 294
AED 667 total
includes taxes & fees
6 Oct - 7 Oct
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
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 stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is AED 374
AED 958 total
includes taxes & fees
14 Oct - 15 Oct
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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 AED 386
AED 759 total
includes taxes & fees
26 Oct - 27 Oct
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A deck with a view of a lake, surrounded by various signs and advertisements.

6. 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 AED 595
AED 2,544 total
includes taxes & fees
18 Oct - 19 Oct
Victorian Inn Elkhart Lake Wisconsin
A living room with a fireplace, a large clock, and a dining area with wooden furniture.

7. 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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is AED 529
AED 636 total
includes taxes & fees
7 Oct - 8 Oct
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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
Logan Ave Holiday House - Upper
A two-story residential building with a flat roof, a front entrance, and a small porch area.

9. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (30 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is AED 433
AED 1,412 total
includes taxes & fees
6 Oct - 7 Oct
Sleeps 8 & Spacious!
A bathroom with white shelves holding wicker baskets and a potted plant.

10. 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 AED 441
AED 830 total
includes taxes & fees
5 Oct - 6 Oct
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

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 AED 430
AED 817 total
includes taxes & fees
5 Oct - 6 Oct
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern living room with a ceiling fan, two sofas, a coffee table, and a TV.

12. Close to Downtown & Shore | Great Location

Close to Downtown & Shore | Great Location
Sheboygan
9.0 out of 10, Wonderful, (10 reviews)
"Have stayed in all but one unit on this property and i must say, they are absolutely amazing!"
United States
Elizabeth S.
The price is AED 399
AED 1,228 total
includes taxes & fees
4 Oct - 5 Oct
Close to Downtown & Shore | Great Location
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

13. 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 AED 416
AED 1,252 total
includes taxes & fees
6 Oct - 7 Oct
Beautiful & Convenient!
A dining table with a vase of green leaves and a candle.

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 AED 459
AED 876 total
includes taxes & fees
1 Nov - 2 Nov
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A dining area with a table, chairs, and a window with curtains.

15. 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 AED 533
AED 951 total
includes taxes & fees
20 Oct - 21 Oct
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
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 traveler
The price is AED 562
AED 1,588 total
includes taxes & fees
26 Oct - 27 Oct
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A cabin with a deck, a covered porch, and a paved driveway.

17. The Esker Ridge Chalet, Pristine Elkhart Solitude

The Esker Ridge Chalet, Pristine Elkhart Solitude
Elkhart Lake
10.0 out of 10, Exceptional, (70 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 AED 731
AED 1,000 total
includes taxes & fees
6 Oct - 7 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

18. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (28 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 AED 486
AED 835 total
includes taxes & fees
4 Oct - 5 Oct
2nd floor loft near the lake!
Beach

19. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
6.8 out of 10, (5 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 AED 716
AED 2,402 total
includes taxes & fees
4 Oct - 5 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.
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Top Sheboygan Hotel Reviews

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Truly a great hotel, well run and well looked after. The rooms are large and spacious with everything you need, and very practical, Right on the river, great location and downtown in 2 mins. ."
Jonathan 18-night trip
Posted 5 hours ago
Watershed Hotel

Frequently asked questions

Can I find a vacation rental in Sheboygan?

Yes, we offer vacation rentals in Sheboygan close to John Michael Kohler Arts Center, or you can go with a more remote option if you want 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 vacation home rentals in Sheboygan?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: This Sheboygan vacation home rental 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 vacation with amenities like a selection of games. Our travelers also rate REMODELED HOME ON LAKE MICHIGAN as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 95 Expedia vacation rentals in Sheboygan for a memorable vacation.

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 vacation rental in Sheboygan like?

A vacation rental is a private property where you can stay for a long or short time in Sheboygan. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll feel right at home. If you're concerned about cleanliness, vacation rentals can offer a sense of privacy away from shared hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great option for a family getaway.