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Sheboygan Vacation Rentals

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Vacation Rentals in Sheboygan

Lobby
Grandstay Residential Suites Hotel - Sheboygan
Grandstay Residential Suites Hotel - Sheboygan
2.5 star property
8.6 out of 10, Excellent, (987)
"Very friendly staff, clean establishment from inside and out. "
United States
Kimberly
$117 nightly
The price is $133
Nov 2 - Nov 3
Total with taxes and fees
Grandstay Residential Suites Hotel - Sheboygan
Terrace/patio
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
2.0 star property
$1,165 nightly
The price is $1,229
Nov 7 - Nov 8
Total with taxes and fees
Brand new Modern, 6 bedroom waterfront home on a beautiful Long Lake.
Bar (on property)
First Floor Pet Friendly Queen Suite with Single Pull-out
First Floor Pet Friendly Queen Suite with Single Pull-out
10.0 out of 10, Exceptional, (2)
"So convenient to all things Elkhart Lake. Great accommodations and host. Would highly recommend!"
United States
Brenda H.
$255 nightly
The price is $277
Nov 2 - Nov 3
Total with taxes and fees
First Floor Pet Friendly Queen Suite with Single Pull-out
House (2 Bedrooms) | Interior
Large Backyard, Walk to Hospital: Sheboygan Abode!
Large Backyard, Walk to Hospital: Sheboygan Abode!
3.0 star property
$376 nightly
The price is $423
Nov 2 - Nov 3
Total with taxes and fees
Large Backyard, Walk to Hospital: Sheboygan Abode!
Private kitchen
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
2.0 star property
9.6 out of 10, Exceptional, (12)
"We absolutely loved the place. Our host was wonderful and accommodating. It was clean, perfect walking distance from the beach and downtown bars and restaurants. Thanks for such a wonderful stay!"
United States
Taylor F.
$135 nightly
The price is $153
Nov 3 - Nov 4
Total with taxes and fees
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.
Exterior
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
10.0 out of 10, Exceptional, (113)
"We enjoyed our stay and quick access to the lake. We enjoyed Sheboygan and the nearby park. Home was extremely clean and easy process."
United States
Shelby L.
$150 nightly
The price is $158
Dec 1 - Dec 2
Total with taxes and fees
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Fridge, microwave, oven, stovetop
*NEW* Beautiful & Convenient!
*NEW* Beautiful & Convenient!
9.8 out of 10, Exceptional, (19)
"The accommodations were very nice! Plenty of space for our family and it was very clean. "
United States
Rebecca W.
$277 nightly
The price is $315
Nov 3 - Nov 4
Total with taxes and fees
*NEW* Beautiful & Convenient!
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
9.8 out of 10, Exceptional, (22)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
$115 nightly
The price is $131
Nov 4 - Nov 5
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Smart TV, books
Newly Updated! Downtown & Shore
Newly Updated! Downtown & Shore
9.6 out of 10, Exceptional, (4)
"Clean, spacious, and quiet. "
United States
Thomas S.
$274 nightly
The price is $311
Nov 3 - Nov 4
Total with taxes and fees
Newly Updated! Downtown & Shore
Exterior detail
Logan Ave Holiday House - Upper
Logan Ave Holiday House - Upper
9.4 out of 10, Exceptional, (3)
"Very clean and well kept!"
United States
Pat R.
$332 nightly
The price is $377
Dec 2 - Dec 3
Total with taxes and fees
Logan Ave Holiday House - Upper
Interior
Gleason's Chouse
Gleason's Chouse
10.0 out of 10, Exceptional, (41)
"So interesting and comfy atmosphere. We loved all the attention to detail. Great amneties. Definitely going back!"
United States
Jenee S.
$183 nightly
The price is $193
Nov 3 - Nov 4
Total with taxes and fees
Gleason's Chouse
Fridge, microwave, oven, stovetop
The Beach town bungalow
The Beach town bungalow
2.0 star property
$179 nightly
The price is $182
Nov 2 - Nov 3
Total with taxes and fees
The Beach town bungalow
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
9.4 out of 10, Exceptional, (8)
"The property was spotless - extremely clean and I appreciated that very much. I had to search to find the bathroom and the vanity was so small it did not allow ease to get ready. I was looking for a book about the property and how the host preferred you leave it (example: bedding removed, etc.) So I had to guess. I slept in the one room one night but the bed was too soft so I switched rooms and slept in the other bed which was much better. "
United States
Kristine
$163 nightly
The price is $185
Nov 2 - Nov 3
Total with taxes and fees
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
3 bedrooms, iron/ironing board, WiFi, bed sheets
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
10.0 out of 10, Exceptional, (3)
"Needed somewhere clean, safe and affordable to bring our family for a few days worth of a family wedding. This home was perfect for us. The space was clean and welcoming. Communication was easy. Close to everything we needed plus some. "
United States
Patricia O.
$176 nightly
The price is $200
Nov 2 - Nov 3
Total with taxes and fees
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI
Property grounds
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
10.0 out of 10, Exceptional, (1)
"In town for family celebration. This was a convenient location to my parent’s home! Thanks!"
United States
Shelly E.
$163 nightly
The price is $185
Nov 11 - Nov 12
Total with taxes and fees
Beachy 3-bedroom upper with WiFi and AC minutes from Lake Michigan
Property grounds
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
10.0 out of 10, Exceptional, (31)
"We came just to relax and have fun. We enjoyed sitting out on the patio with our dog and books and having a bonfire in the fire pit. The home is very well labeled and cozy—we loved it! "
United States
Jeremy E.
$225 nightly
The price is $255
Nov 26 - Nov 27
Total with taxes and fees
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Living area
2nd floor loft near the lake!
2nd floor loft near the lake!
9.8 out of 10, Exceptional, (15)
"My family and I had a great stay at this property. Quiet neighbors and plenty of parking available. Host was prompt to reply to our questions. Also, thank you for the chocolates! Looking forward to booking this property in the future."
United States
Victor F.
$215 nightly
The price is $244
Nov 12 - Nov 13
Total with taxes and fees
2nd floor loft near the lake!
Smart TV, books
*NEW* Sleeps 8 & Spacious!
*NEW* Sleeps 8 & Spacious!
10.0 out of 10, Exceptional, (27)
"Very clean and very comfortable beds"
United States
douglas c.
$315 nightly
The price is $358
Nov 3 - Nov 4
Total with taxes and fees
*NEW* Sleeps 8 & Spacious!
Fridge, oven, stovetop, dishwasher
Surfside Retreat – Walk to Lake
Surfside Retreat – Walk to Lake
$250 nightly
The price is $254
Nov 16 - Nov 17
Total with taxes and fees
Surfside Retreat – Walk to Lake
Fridge, microwave, oven, stovetop
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
10.0 out of 10, Exceptional, (4)
"The house is very comfortable inside and outside. It has an enclosed back yard for grilling and chilling. The beds are comfortable. The kitchen is equipped for any meal you want to create. The host is very helpful and responded quickly to any questions I had. I will use this home again!"
United States
Pete J.
$168 nightly
The price is $191
Nov 3 - Nov 4
Total with taxes and fees
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit
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
"I liked everything- exceptionally clean- great room - great bed- breakfast was very good 👍"
Dan 1-night trip
Posted 20 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 Blue Harbor Resort & Conference Center Water Park, 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?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: This Sheboygan vacation home rental is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. 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 Bookworm Gardens, or simply take in cultural attractions like John Michael Kohler Arts Center and Stefanie H. Weill Center for the Performing Arts. While here, Blue Harbor Resort & Conference Center Water Park and Kohler-Andrae State 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.