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Sheboygan Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

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, (1,062 reviews)
"Great place to stay breakfast was good then room was good. Staff were great as well only issue is the pool is tiny."
United States
Devin
$184 nightly
The price is $209
Aug 3 - Aug 4
Total with taxes and fees
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, (30 reviews)
"Communicative host, good location, comfortable and clean apartment. "
United States
Hannah T.
$115 nightly
The price is $131
Aug 6 - Aug 7
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
3 bedrooms, iron/ironing board, travel crib, WiFi

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
10.0 out of 10, Exceptional, (7 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
$244 nightly
The price is $277
Aug 24 - Aug 25
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Dining

4. 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, (23 reviews)
"The stay was great ! Had lots of fun definitely will be back ."
United States
Zay B.
$261 nightly
The price is $296
Aug 23 - Aug 24
Total with taxes and fees
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
Interior

5. 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.
$368 nightly
The price is $417
Aug 19 - Aug 20
Total with taxes and fees
Sleeps 8 & Spacious!
Exterior detail

6. Apartment Centrally Located

Apartment Centrally Located
Plymouth
$251 nightly
The price is $253
Aug 3 - Aug 4
Total with taxes and fees
Apartment Centrally Located
Apartment (2 Bedrooms) | Front of property

7. Modern South Pier Condo on Sheboygan River!

Modern South Pier Condo on Sheboygan River!
4.0 star property
Sheboygan
$349 nightly
The price is $396
Aug 27 - Aug 28
Total with taxes and fees
Modern South Pier Condo on Sheboygan River!
Smart TV, books

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.
$326 nightly
The price is $370
Aug 24 - Aug 25
Total with taxes and fees
Beautiful & Convenient!
Smart TV

9. 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, (18 reviews)
"Nice place, exactly as pictured. Enjoyed the coffee bar"
United States
Sylvia L.
$261 nightly
The price is $296
Aug 3 - Aug 4
Total with taxes and fees
3 Blocks from Beach house 1 BDRM full bath 4 min to downtown,sleeps 4
Exterior

10. Logan Ave Holiday House - Upper

Logan Ave Holiday House - Upper
Sheboygan
9.8 out of 10, Exceptional, (6 reviews)
"Property was very nice. Would stay here again. "
United States
Janice
$349 nightly
The price is $396
Aug 25 - Aug 26
Total with taxes and fees
Logan Ave Holiday House - Upper
TV

11. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
Sheboygan
10.0 out of 10, Exceptional, (1 review)
"Great place to stay, the area is safe and close to the Marina. Owner/host was excellent to communicate with."
United States
Mary A.
$372 nightly
The price is $422
Aug 3 - Aug 4
Total with taxes and fees
Large Backyard, Walk to Hospital: Sheboygan Abode!
3 bedrooms, desk, iron/ironing board, travel crib

12. 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.
$200 nightly
The price is $227
Aug 5 - Aug 6
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
TV

13. Apartment Centrally Located

Apartment Centrally Located
Plymouth
10.0 out of 10, Exceptional, (2 reviews)
"Convenient location in between Road America, Elkhart Lake, and Plymouth. You're about 10 minutes from everything you stay in the area for.The apartment is a dorm, but it's clean and quiet and was perfect for spending our nights while watching the races at Road America."
United States
Brian H.
Apartment Centrally Located
Smart TV

14. 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, (32 reviews)
"Great value. Cheaper and better than any hotel. "
United States
Nicholas R.
$377 nightly
The price is $428
Aug 11 - Aug 12
Total with taxes and fees
Pet friendly, freshly renovated, 5 minute walk to beach in the heart of the city
Interior

15. 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.
$245 nightly
The price is $278
Aug 18 - Aug 19
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
TV

16. Apartment Centrally Located

Apartment Centrally Located
Plymouth
9.2 out of 10, Wonderful, (5 reviews)
"Great, reasonable priced apartment.. it was quiet and had everything I needed.. very comfortable"
United States
Diana A.
Apartment Centrally Located
House (2 Bedrooms) | Interior

17. Large Backyard, Walk to Hospital: Sheboygan Abode!

Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
Sheboygan
$365 nightly
The price is $414
Aug 3 - Aug 4
Total with taxes and fees
Large Backyard, Walk to Hospital: Sheboygan Abode!
Dining

18. Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan

Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Sheboygan
7.8 out of 10, Good, (7 reviews)
"great location walkable to downtown and Lake Michigan. Very centrally located."
United States
Laura A.
$377 nightly
The price is $424
Aug 18 - Aug 19
Total with taxes and fees
Huron Ave · Spacious & Peaceful Home in the heart of Sheboygan
Dining

19. 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, (7 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.
$312 nightly
The price is $354
Aug 24 - Aug 25
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Dining

20. 4 Bedroom Home on the River with Private River access

4 Bedroom Home on the River with Private River access
Sheboygan
9.8 out of 10, Exceptional, (41 reviews)
"If you are looking for a quiet and calm place to enjoy your morning coffee or watch a sunset, this is the perfect place!"
United States
Sharon R.
$351 nightly
The price is $398
Aug 13 - Aug 14
Total with taxes and fees
4 Bedroom Home on the River with Private River access
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

10/10 Excellent
"Nice hotel in a great location. Rooms are big and comfortable!"
Craig 4-night trip
Posted 17 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 $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 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.