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Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

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, (1,072 reviews)
"Nice place and good breakfast"
United States
Kristin
$143 nightly
The price is $162
Aug 23 - Aug 24
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, (30 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
$115 nightly
The price is $131
Aug 21 - Aug 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
10.0 out of 10, Exceptional, (24 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$235 nightly
The price is $267
Sep 8 - Sep 9
Total with taxes and fees
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.

4. Sleeps 8 & Spacious!

Sleeps 8 & Spacious!
Sheboygan
10.0 out of 10, Exceptional, (28 reviews)
"Great location! Roomy, close to everything, very nice inside, clean, always found parking."
United States
Beth D.
$329 nightly
The price is $373
Aug 23 - Aug 24
Total with taxes and fees
Sleeps 8 & Spacious!
A bedroom with a wooden bed, white bedding, and a painting of a snowy landscape.

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, (9 reviews)
"We enjoyed our stay and found the place very comfortable for our family of five. It was easy to walk down to see the lake and a quick drive to restaurants in town."
United States
Amanda
$164 nightly
The price is $186
Sep 1 - Sep 2
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
An indoor water park with multiple slides and play structures.

6. 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, (140 reviews)
"Great little cottage. Perfect for a night away "
United States
James R.
$165 nightly
The price is $174
Sep 1 - Sep 2
Total with taxes and fees
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.

7. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (7 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
$301 nightly
The price is $342
Sep 2 - Sep 3
Total with taxes and fees
Logan Ave Holiday House - Upper
A modern living room with a grey sofa, a white armchair, a round coffee table, and a side table with a lamp.

8. Beautiful & Convenient!

Beautiful & Convenient!
Sheboygan
9.8 out of 10, Exceptional, (21 reviews)
"Place was clean and had everything we needed! "
United States
stormy a.
$297 nightly
The price is $337
Aug 31 - Sep 1
Total with taxes and fees
Beautiful & Convenient!

9. 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.
$188 nightly
The price is $214
Aug 20 - Aug 21
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

10. 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)
"Really nice place, everything was perfect! The shower downstairs doesn’t get very hot, but the one upstairs makes up for it. Great location and neighborhood. The garage was a huge help since it dumped 6” of snow while we were there (the owners offering to shovel). The fireplace was really awesome, and my teenage daughter really enjoyed having the entire upstairs to herself. Overall, very happy with our stay."
United States
Kevin K.
$391 nightly
The price is $444
Sep 16 - Sep 17
Total with taxes and fees
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
A living room with a sofa, coffee table, and TV.

11. 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, (35 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
$377 nightly
The price is $428
Aug 23 - Aug 24
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
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.
$217 nightly
The price is $246
Sep 14 - Sep 15
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
A bathroom with white shelves holding wicker baskets and a potted plant.

13. 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.
$197 nightly
The price is $224
Aug 20 - Aug 21
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

14. 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
Aug 23 - Aug 24
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

15. 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
Aug 23 - Aug 24
Total with taxes and fees
Updated Plymouth Home ~ 5 Mi to Road America!
A spacious living room with a sofa, coffee table, and a TV. There is a ceiling fan, a fireplace, and a large window.

16. The Beach town bungalow

The Beach town bungalow
Sheboygan
$394 nightly
The price is $401
Sep 4 - Sep 5
Total with taxes and fees
The Beach town bungalow
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, (65 reviews)
"Absolutely Beautiful. Great, quiet location...clean and well kept. Recommend buying some of their amazing home made maple syrup!!"
United States
Barbara
$261 nightly
The price is $275
Sep 1 - Sep 2
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.

18. Sheboygan Riverside Condo

Sheboygan Riverside Condo
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Nice quiet place. Would stay again."
United States
Tressie J.
$282 nightly
The price is $287
Aug 20 - Aug 21
Total with taxes and fees
Sheboygan Riverside Condo
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, (12 reviews)
"Home was very clean and had everything we needed. Beds were comfortable. Easy to find and close to everything. "
United States
Andrea S.
$592 nightly
The price is $672
Aug 23 - Aug 24
Total with taxes and fees
The Links! - Luxury Golf Retreat with Golf Simulator
A cozy seating area with a bench and cushions, a wooden floor, and a view through large windows.

20. 2nd floor loft near the lake!

2nd floor loft near the lake!
Manitowoc
9.8 out of 10, Exceptional, (24 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.
$218 nightly
The price is $247
Aug 30 - Aug 31
Total with taxes and fees
2nd floor loft near the lake!
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

La Quinta Inn by Wyndham Sheboygan

La Quinta Inn by Wyndham Sheboygan

10/10 Excellent
"Clean room, Breakfast was well varied and complete. Staff was friendly and accommodating. Great nights stay and would do it again."
Eric 1-night trip
Posted 3 hours ago
La Quinta Inn by Wyndham 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 $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?

REMODELED HOME ON LAKE MICHIGAN: This Sheboygan vacation home rental is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind. Our travelers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 94 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, Blue Harbor Resort & Conference Center Water Park and Bookworm Gardens 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.