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Sheboygan Vacation Rentals

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Sep 24 - Sep 25
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Sep 26 - Sep 28
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Oct 3 - Oct 5

Vacation Rentals in Sheboygan

Our top choices for Sheboygan vacation rentals

Grandstay Residential Suites Hotel - Sheboygan
Lobby

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
8.6 out of 10, Excellent, (970)
"It has everything that we needed and the breakfast was good. Clean and staff was friendly. "
The price is ￥17,104
￥19,413 total
includes taxes & fees
Oct 8 - Oct 9
Grandstay Residential Suites Hotel - Sheboygan
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Fridge, microwave, oven, stovetop

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

9.8 out of 10, Exceptional, (250)
"We really enjoyed our stay. Very clean and easy check in process. Would highly recommend to anyone considering staying here. "
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Fridge, microwave, oven, stovetop

Lake Michigan Home with gorgeous views, great spot for family or golf retreat

10.0 out of 10, Exceptional, (116)
"Beautiful view, lovely setting! We loved the large windows. "
Lake Michigan Home with gorgeous views, great spot for family or golf retreat
Beach front luxury spacious villa !
Fireplace, books

Beach front luxury spacious villa !

10.0 out of 10, Exceptional, (69)
"Our family enjoyed our long weekend at your property. It was a great way to spend time together with everything we expected from the listing. Would definitely stay again. "
Beach front luxury spacious villa !
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Fridge, microwave, oven, stovetop

Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

9.8 out of 10, Exceptional, (17)
"Top notch, close to everything you want in Sheboygan "
The price is ￥14,023
￥19,268 total
includes taxes & fees
Sep 28 - Sep 29
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Marina

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

10.0 out of 10, Exceptional, (104)
"Great stay close to marina and restaurants "
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Smart TV

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

9.6 out of 10, Exceptional, (5)
"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. "
The price is ￥15,155
￥27,260 total
includes taxes & fees
Oct 7 - Oct 8
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Lakeview Farm | Beach · Hot Tub · Theater · Views
Terrace/patio

Lakeview Farm | Beach · Hot Tub · Theater · Views

10.0 out of 10, Exceptional, (1)
"Fun time! Very buggy by the lake but not much you can do about that. "
Lakeview Farm | Beach · Hot Tub · Theater · Views
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
Fridge, microwave, oven, stovetop

Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

10.0 out of 10, Exceptional, (2)
"All of us, ages 5-75 had a wonderful time. Plenty of activities but also places to relax. We especially enjoyed the beautiful yard, the pool and spa & the well equipped kitchen."
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX
BEACHSIDE GETAWAY IN SHEBOYGAN
Interior

BEACHSIDE GETAWAY IN SHEBOYGAN

10.0 out of 10, Exceptional, (26)
"We were up there racing in MotoAmerica. Was close to the track and was perfect for our stay."
BEACHSIDE GETAWAY IN SHEBOYGAN
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan
Terrace/patio

Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

10.0 out of 10, Exceptional, (2)
"Great place to stay. The lake views were amazing!"
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
Exterior detail

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

9.8 out of 10, Exceptional, (11)
"We really enjoyed our stay at this property. The location was great for our trip to Road America racetrack. Very clean home with updated everything! Thank you so much!!"
The price is ￥19,498
￥52,140 total
includes taxes & fees
Oct 8 - Oct 9
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan
4 Bedroom Home on the River with Private River access
Fridge, microwave, oven, stovetop

4 Bedroom Home on the River with Private River access

9.8 out of 10, Exceptional, (31)
"All was as advertised. Perfect space for what we were looking for."
4 Bedroom Home on the River with Private River access
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
Property grounds

2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

10.0 out of 10, Exceptional, (187)
"We had a lovely stay! Beautiful view and loved the hot tub! "
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub
*NEW* Beautiful & Convenient!
Smart TV, books

*NEW* Beautiful & Convenient!

10.0 out of 10, Exceptional, (18)
"Place was clean and had everything we needed! "
The price is ￥15,549
￥45,126 total
includes taxes & fees
Oct 21 - Oct 22
*NEW* Beautiful & Convenient!
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Fridge, microwave, oven, stovetop

The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

10.0 out of 10, Exceptional, (35)
"The property was quite cozy with a great fenced-in backyard, conveniently located near the little downtown and Lake Michigan. Couldn't have asked for more!"
The price is ￥20,679
￥61,360 total
includes taxes & fees
Oct 8 - Oct 9
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced
Lake Breeze on 11th
Interior

Lake Breeze on 11th

9.8 out of 10, Exceptional, (6)
"We had a great time here. The kids loved the little toy room. We highly recommend this stay when traveling with littles. "
Lake Breeze on 11th
REMODELED HOME ON LAKE MICHIGAN
Property grounds

REMODELED HOME ON LAKE MICHIGAN

9.8 out of 10, Exceptional, (157)
"Beautiful, clean house with spectacular views of Lake Michigan. If we are ever back in the area, we will be staying here, again!"
REMODELED HOME ON LAKE MICHIGAN
Beachside Condo w/ Stunning Lake Views
On the beach

Beachside Condo w/ Stunning Lake Views

10.0 out of 10, Exceptional, (22)
"Beautiful location and accommodations"
Beachside Condo w/ Stunning Lake Views
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
Sun loungers, beach towels

Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony

9.8 out of 10, Exceptional, (19)
"This is a great spot in this destination. Walking distance to a great Italian restaurant and the resort with arcade and waterpark."
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony
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

Harbor Winds Hotel

Harbor Winds Hotel

10/10 Excellent
"Delilah was very welcoming when we arrived. When we told her that we were going fishing in the morning, she made sure the breakfast bar and a fresh pot of coffee was ready for us - that was 4:00am! We will definitely stay here again."
Sandra 3-night trip
Posted 2 days ago
Harbor Winds Hotel

Find out more about Sheboygan

Find out more about Sheboygan

Search for holiday rentals in Sheboygan on Expedia! You can easily find your home rentals, villas, holiday apartments in Sheboygan using one of the methods below:

  • View our selection of featured holiday rentals in Sheboygan
  • Use the map to find apartments and other holiday homes in the Sheboygan neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Sheboygan while they last

Look no further and take a look at our great range of rental properties in Sheboygan!

Explore a world of travel with Expedia

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?

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 Lake Michigan Home with gorgeous views, great spot for family or golf retreat as a favorite home for rent in Sheboygan.

How many vacation rentals will I find in Sheboygan?

Choose from 96 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.