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Sheboygan Vacation Rentals

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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

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, (1,087 reviews)
"Nice place and good breakfast"
United States
Kristin
$125 nightly
The price is $142
Sep 30 - Oct 1
Total with taxes and fees
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
9.6 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.
$115 nightly
The price is $131
Sep 21 - Sep 22
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
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.

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.
$229 nightly
The price is $259
Sep 27 - Sep 28
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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)
"Place was clean and had everything we needed! "
United States
stormy a.
$304 nightly
The price is $345
Oct 6 - Oct 7
Total with taxes and fees
Beautiful & Convenient!
A small, single-story house with a porch, surrounded by a gravel driveway and lush greenery.

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.
$181 nightly
The price is $191
Oct 7 - Oct 8
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
A bedroom with a wooden bed, two bedside tables with lamps, a wall-mounted picture, and a carpeted floor.

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
$176 nightly
The price is $200
Oct 6 - Oct 7
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
A living room with a coffee station, a sofa, a ceiling fan, and a view of the outdoors.

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.
$329 nightly
The price is $373
Oct 14 - Oct 15
Total with taxes and fees
Sleeps 8 & Spacious!
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

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
$366 nightly
The price is $415
Sep 20 - Sep 21
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

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
$377 nightly
The price is $397
Sep 20 - Sep 21
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
A living room with a sofa, coffee table, and 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.
$528 nightly
The price is $599
Sep 21 - Sep 22
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
A modern kitchen with a central island, wooden cabinets, and a built-in stove. There is a dining area with a table and chairs, and a living room with a sofa and a fireplace.

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.
$779 nightly
The price is $884
Sep 21 - Sep 22
Total with taxes and fees
Luxury Lakeside Home-NEW Renovation-Walk to Beach, Dining, & More.
A dining table with a vase of green leaves and a candle.

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.
$228 nightly
The price is $258
Sep 21 - Sep 22
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A two-story house with a front porch, a well-maintained lawn, and a sidewalk leading to the street.

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
$369 nightly
The price is $419
Oct 14 - Oct 15
Total with taxes and fees
Logan Ave Holiday House - Upper
A modern kitchen with a large island, dark blue cabinets, and a stainless steel refrigerator.

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.
$549 nightly
The price is $623
Sep 27 - Sep 28
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator

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.
$722 nightly
The price is $819
Oct 1 - Oct 2
Total with taxes and fees
Edgewater Villa: 4 Bedroom, Sleeps 14!
A bathroom with white shelves holding wicker baskets and a potted plant.

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.
$180 nightly
The price is $204
Oct 6 - Oct 7
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

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.
$722 nightly
The price is $819
Oct 1 - Oct 2
Total with taxes and fees
Just Beachy: 4 Bedroom, Sleeps 12!
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

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
$302 nightly
The price is $343
Sep 20 - Sep 21
Total with taxes and fees
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
A deck with a hot tub, outdoor seating, and a view of a forested area.

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.
$914 nightly
The price is $964
Sep 18 - Sep 19
Total with taxes and fees
Stunning private home hidden in the woods. Can sleep 11 guests
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

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.
$386 nightly
The price is $407
Sep 20 - Sep 21
Total with taxes and fees
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.
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Top Sheboygan Hotel Reviews

Beach front luxury spacious villa !

Beach front luxury spacious villa !

10/10 Excellent
"Beautiful views and the relaxing sounds of the waves made the location perfect."
Keith L. 3-night trip
Posted 13 hours ago
Beach front luxury spacious villa !

Find out more about Sheboygan

Everything you need to know about Sheboygan vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Sheboygan vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Sheboygan vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Sheboygan. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Sheboygan in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Sheboygan rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Sheboygan vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Sheboygan. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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.