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

Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (1,110 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥18,963
￥21,523 total
includes taxes & fees
Nov 1 - Nov 2
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 ￥10,271
￥15,245 total
includes taxes & fees
Oct 21 - Oct 22
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 ￥13,511
￥28,787 total
includes taxes & fees
Oct 20 - Oct 21
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

4. 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 ￥18,618
￥54,670 total
includes taxes & fees
Oct 27 - Oct 28
Beautiful & Convenient!
A deck with a view of a lake, surrounded by various signs and advertisements.

5. 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
Victorian Inn Elkhart Lake Wisconsin
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 ￥26,310
￥49,234 total
includes taxes & fees
Nov 1 - Nov 2
Riverfront Loft - FANTASTIC location w/stunning views - on the boardwalk!
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, (149 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥22,123
￥26,674 total
includes taxes & fees
Nov 9 - Nov 10
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A bathroom with white shelves holding wicker baskets and a potted plant.

8. 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 ￥16,592
￥32,642 total
includes taxes & fees
Nov 10 - Nov 11
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
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 ￥14,933
￥31,478 total
includes taxes & fees
Oct 20 - Oct 21
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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.

10. 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 ￥21,333
￥48,068 total
includes taxes & fees
Oct 25 - Oct 26
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

11. 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
Sleeps 8 & Spacious!
A dining area with a table, chairs, and a window with curtains.

12. 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 ￥18,962
￥35,870 total
includes taxes & fees
Nov 16 - Nov 17
Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
A laundry room with two front-loading washing machines, a shelf with cleaning supplies, and a green ironing board.

13. 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 ￥17,777
￥34,168 total
includes taxes & fees
Oct 27 - Oct 28
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

14. 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 ￥18,646
￥52,909 total
includes taxes & fees
Nov 18 - Nov 19
Logan Ave Holiday House - Upper
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

15. 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 ￥18,488
￥60,981 total
includes taxes & fees
Nov 16 - Nov 17
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A hotel room with two beds, a dining area, and a view of the outdoors.

16. Victorian Inn #241 | 2 Queen Beds

Victorian Inn #241 | 2 Queen Beds
Elkhart Lake
The price is ￥15,091
￥27,575 total
includes taxes & fees
Oct 20 - Oct 21
Victorian Inn #241 | 2 Queen Beds
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, (71 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 ￥31,446
￥42,179 total
includes taxes & fees
Oct 20 - Oct 21
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, (30 reviews)
"Clean , quiet, great host. Property had everything we needed for a two day stay."
United States
Tim C.
The price is ￥20,906
￥36,104 total
includes taxes & fees
Oct 20 - Oct 21
2nd floor loft near the lake!
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

19. 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)
"Perfect trip and great location"
United States
Kristian N.
The price is ￥35,555
￥97,390 total
includes taxes & fees
Oct 20 - Oct 21
The Links! - Luxury Golf Retreat with Golf Simulator
A living room with a sofa, coffee table, and TV.

20. 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, (43 reviews)
"This nice big house has a great location for visiting Sheboygan and Lake Michigan. It was easy to walk to excellent restaurants and vintage stores. We also caught the Wednesday farmers market and saw the pops band concert that night. The house is well air-conditioned and comfortable. Great stay!"
United States
Nikki M.
The price is ￥49,776
￥95,417 total
includes taxes & fees
Oct 20 - Oct 21
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

10/10 Excellent
"This is a very scenic property with a lake view. Nice spot for a relaxing girl's trip. Nice location as well. The check in was very easy. The two bedrooms are upstairs, and the bathrooms were on the 1st floor and basement, we are older women, and I was not aware of this."
Laura G. 2-night trip
Posted 4 hours ago
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

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 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.