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

Sheboygan Vacation 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
Oct 2 - Oct 4
In two months
Nov 13 - Nov 15
In three months
Dec 11 - Dec 13
In four months
Jan 8 - Jan 10

Our top choices for Sheboygan vacation 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, (1,089 reviews)
"Nice place and good breakfast"
United States
Kristin
The price is ￥15,814
￥17,949 total
includes taxes & fees
Sep 27 - Sep 28
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, (33 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 ￥14,904
￥18,520 total
includes taxes & fees
Sep 22 - Sep 23
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
9.8 out of 10, Exceptional, (30 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
The price is ￥16,096
￥40,704 total
includes taxes & fees
Sep 27 - Sep 28
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Smart TV, books

4. 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 ￥17,244
￥52,514 total
includes taxes & fees
Sep 21 - Sep 22
Beautiful & Convenient!
Exterior

5. 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, (145 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
The price is ￥25,101
￥29,958 total
includes taxes & fees
Oct 7 - Oct 8
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
3 bedrooms, desk, iron/ironing board, travel crib

6. 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 ￥15,688
￥31,340 total
includes taxes & fees
Oct 6 - Oct 7
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Interior

7. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (29 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
The price is ￥17,953
￥59,551 total
includes taxes & fees
Oct 20 - Oct 21
Sleeps 8 & Spacious!
Coffee/tea maker, fridge, microwave, oven

8. 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 ￥26,670
￥71,224 total
includes taxes & fees
Oct 20 - Oct 21
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
House (3 Bedrooms) | Interior

9. Updated Plymouth Home ~ 5 Mi to Road America!

Updated Plymouth Home ~ 5 Mi to Road America!
3.0 star property
Plymouth
10.0 out of 10, Exceptional, (3 reviews)
"Everything was great, very convenient to Road America."
United States
Kelis
Updated Plymouth Home ~ 5 Mi to Road America!
Smart TV

10. 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, (42 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
The price is ￥31,768
￥71,313 total
includes taxes & fees
Sep 21 - Sep 22
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Coffee/tea maker, fridge, microwave, oven

11. Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.

Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Sheboygan
10.0 out of 10, Exceptional, (17 reviews)
"Everything was clean and spacious. Had a great time and would definitely stay again! "
United States
Brad T.
The price is ￥68,870
￥138,708 total
includes taxes & fees
Sep 21 - Sep 22
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
Dining

12. 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 ￥17,649
￥34,989 total
includes taxes & fees
Sep 21 - Sep 22
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Exterior

13. 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 ￥21,336
￥56,267 total
includes taxes & fees
Oct 20 - Oct 21
Logan Ave Holiday House - Upper
Coffee/tea maker, fridge, microwave, oven

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

The Links! - Luxury Golf Retreat with Golf Simulator
Sheboygan
10.0 out of 10, Exceptional, (14 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 ￥35,298
￥96,687 total
includes taxes & fees
Sep 27 - Sep 28
The Links! - Luxury Golf Retreat with Golf Simulator
Exterior

15. Edgewater Villa: 4 Bedroom, Sleeps 14!

Edgewater Villa: 4 Bedroom, Sleeps 14!
Sheboygan
8.2 out of 10, Very good, (16 reviews)
"Nice property, close to the beach. It was perfect for our weekend getaway. "
United States
Rebecca B.
The price is ￥69,812
￥129,803 total
includes taxes & fees
Oct 19 - Oct 20
Edgewater Villa: 4 Bedroom, Sleeps 14!
Interior

16. 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 ￥16,472
￥32,050 total
includes taxes & fees
Oct 6 - Oct 7
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Exterior

17. Just Beachy: 4 Bedroom, Sleeps 12!

Just Beachy: 4 Bedroom, Sleeps 12!
Sheboygan
8.4 out of 10, Very good, (7 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 ￥69,812
￥128,556 total
includes taxes & fees
Oct 1 - Oct 2
Just Beachy: 4 Bedroom, Sleeps 12!
3 bedrooms, iron/ironing board, WiFi, bed sheets

18. Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair

Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
Sheboygan
The price is ￥41,416
￥53,596 total
includes taxes & fees
Sep 21 - Sep 22
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
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 ￥125,504
￥151,275 total
includes taxes & fees
Sep 21 - Sep 22
Stunning private home hidden in the woods. Can sleep 11 guests
Coffee/tea maker, fridge, microwave, stovetop

20. 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.
Updated Plymouth Home ~ 5 Mi to Road America!
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

Fairfield Inn & Suites by Marriott Sheboygan

Fairfield Inn & Suites by Marriott Sheboygan

8/10 Good
"Very Clean. Rooms were a really good size."
Napolean 2-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Sheboygan

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
  • Use the map to find apartments and other holiday homes in the Sheboygan neighbourhood you prefer
  • 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. Some other homes for rent in Sheboygan include Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city and REMODELED HOME ON LAKE MICHIGAN.

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 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 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.