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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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, (1,105 reviews)
"Nice place and good breakfast"
United States
Kristin
$127 nightly
The price is $144
Nov 3 - Nov 4
Total with taxes and fees
Grandstay Residential Suites Hotel - 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.

2. 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.
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.

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, (32 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$230 nightly
The price is $261
Oct 14 - Oct 15
Total with taxes and fees
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.

4. 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
$170 nightly
The price is $193
Nov 2 - Nov 3
Total with taxes and fees
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.

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
$644 nightly
The price is $706
Oct 11 - Oct 12
Total with taxes and fees
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, (17 reviews)
"Every detail was thought of and the host went out above and beyond to make it a memorable stay. "
United States
Melissa D.
$297 nightly
The price is $337
Nov 1 - Nov 2
Total with taxes and fees
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, (146 reviews)
"Super clean and a nice quiet place to stay!"
United States
Elisabeth D.
$164 nightly
The price is $173
Oct 14 - Oct 15
Total with taxes and fees
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.
$188 nightly
The price is $213
Oct 20 - Oct 21
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A dining area with a table, chairs, and a window with curtains.

9. Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan

Eclectic Artsy 3-bedroom house with King Bed & AC in Sheboygan
Sheboygan
$215 nightly
The price is $244
Nov 2 - Nov 3
Total with taxes and fees
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.

10. 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, (13 reviews)
"We enjoyed our stay! The property was clean, "
United States
Benjamin B.
$181 nightly
The price is $205
Nov 2 - Nov 3
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A dining table with a vase of green leaves and a candle.

11. 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.
$210 nightly
The price is $238
Nov 1 - Nov 2
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

12. 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
Nov 2 - Nov 3
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A cabin with a deck, a covered porch, and a paved driveway.

13. 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
$259 nightly
The price is $273
Oct 13 - Oct 14
Total with taxes and fees
The Esker Ridge Chalet, Pristine Elkhart Solitude
A modern kitchen with a central island, a dining area with a coffee table, a sofa, and a TV mounted on the wall.

14. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (2 reviews)
"Nice quiet place. Would stay again."
United States
Tressie J.
$331 nightly
The price is $337
Oct 12 - Oct 13
Total with taxes and fees
Sheboygan Riverside Condo
Beach

15. Beachfront Paradise: King Suite - Sleeps 8!

Beachfront Paradise: King Suite - Sleeps 8!
Sheboygan
7.0 out of 10, Good, (6 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.
$576 nightly
The price is $654
Oct 12 - Oct 13
Total with taxes and fees
Beachfront Paradise: King Suite - Sleeps 8!
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

16. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (29 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.
$200 nightly
The price is $227
Oct 12 - Oct 13
Total with taxes and fees
2nd floor loft near the lake!
A living room with a sofa, coffee table, and TV.

17. 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.
$532 nightly
The price is $604
Oct 11 - Oct 12
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 large island, dark blue cabinets, and a stainless steel refrigerator.

18. 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.
$543 nightly
The price is $616
Oct 12 - Oct 13
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator
A neatly made bed with a wooden headboard, a nightstand with a lamp, and a large mirror.

19. 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
10.0 out of 10, Exceptional, (1 review)
"Just like the description. Very clean. Accommodations for kids and the host was very accommodating!"
United States
Erin S.
$302 nightly
The price is $343
Oct 11 - Oct 12
Total with taxes and fees
Eve’s Place by beach + 2 kings 1 queen + AC + Pack’n Play + High Chair
May 10, 2024

20. 4 bed house on the shore of Lake Michigan

4 bed house on the shore of Lake Michigan
Belgium
9.4 out of 10, Exceptional, (83 reviews)
"Location and privacy exceptional."
United States
michael g.
$370 nightly
The price is $390
Nov 2 - Nov 3
Total with taxes and fees
4 bed house on the shore of Lake Michigan
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

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

8/10 Good
"😊"
Victoria 2-night trip
Posted 22 hours ago
Grandstay Residential Suites Hotel - Sheboygan

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 $144 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. 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.