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Holiday Rentals in Sheboygan

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Holiday Rentals in Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 star property
Downtown Sheboygan
8.6 out of 10, Excellent, (997)
"Very nice room, very clean. Staff very nice"
United States
Laura
The price is €123
includes taxes & fees
11 Nov - 12 Nov
Grandstay Residential Suites Hotel - Sheboygan

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

Sheboygan
9.8 out of 10, Exceptional, (254)
"Wonderful views of the lake close to all that Sheboygan has to offer. Enjoyed our stay. Thank you for sharing!"
United States
James R.
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

Sheboygan
10.0 out of 10, Exceptional, (120)
"Beautiful view, lovely setting! We loved the large windows. "
United States
Amanda L.
Lake Michigan Home with gorgeous views, great spot for family or golf retreat

Beach front luxury spacious villa !

Sheboygan
10.0 out of 10, Exceptional, (74)
"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. "
United States
Gary F.
Beach front luxury spacious villa !

Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

Sheboygan
10.0 out of 10, Exceptional, (109)
"Nice condo. Comfortable beds. "
United States
Jennie K.
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

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

Ellis Historical District
9.8 out of 10, Exceptional, (23)
"Top notch, close to everything you want in Sheboygan "
United States
Cody
The price is €117
includes taxes & fees
13 Nov - 14 Nov
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

2.0 star property
Ellis Historical District
9.6 out of 10, Exceptional, (12)
"Place was clean, up to date, easy to access. The place was well stocked with cooking utensils, plates, silverware, etc. The place was very comfortable. Would rebook the next time we are in Sheboygan"
United States
Jay R.
The price is €136
includes taxes & fees
12 Nov - 13 Nov
Cozy 1-bedroom house in Sheboygan walking distance to the lake and downtown.

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

Sheboygan
10.0 out of 10, Exceptional, (22)
"Beautiful, clean accommodations- walkable to the beach- plenty of towels- owners were very prompt at answering questions- would stay again"
United States
Parul M.
Perfect Paradise - Lakeview Condo w/ 7 Beds, Jacuzzi, and Balcony

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Sheboygan
9.2 out of 10, Wonderful, (10)
"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
The price is €164
includes taxes & fees
11 Nov - 12 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Edgewater Escape: 4 Bedroom, Sleeps 14!

Sheboygan
10.0 out of 10, Exceptional, (1)
"A beautiful setting. Very clean and spacious, perfect for our group of seven. I would highly recommend it and and we plan to come back next year. (A few small things of note , the key system was cumbersome but our host was kind enough to come over and help us . The kitchen could use more paper products, dish towels, hotpads and some foil or Saran wrap.)Thank you "
United States
Coleen M.
The price is €556
includes taxes & fees
11 Nov - 12 Nov
Edgewater Escape: 4 Bedroom, Sleeps 14!

BEACHSIDE GETAWAY IN SHEBOYGAN

Sheboygan
10.0 out of 10, Exceptional, (26)
"Our stay was really good. The location of the property was definitely the biggest reason we booked. Easy walking beach access. You have a nice view of the beach from the front and back of the property. The inside was cute and cozy. "
United States
Ann T.
BEACHSIDE GETAWAY IN SHEBOYGAN

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

Sheboygan
10.0 out of 10, Exceptional, (4)
"Awesome place, we loved it!"
United States
Richard S.
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

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

Sheboygan
10.0 out of 10, Exceptional, (188)
"We had a lovely stay! Beautiful view and loved the hot tub! "
United States
Katie B.
2 bed/2 bath Townhouse on a Quiet cul de sac with backyard views and a Hot tub

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

Sheboygan
10.0 out of 10, Exceptional, (2)
"We had an awesome time!! The hosts answered all of our questions fast and helped us know things about the area. We would love to go back!"
United States
Margaret D.
Pelican Point - Private Retreat - just 4 miles to downtown Sheboygan

LUXE Manor with Modern, Elegant Vibes

Sheboygan
10.0 out of 10, Exceptional, (11)
"Jordan is a Hall of Fame host! By the time we left, I felt like we were friends. He goes above and beyond with his willingness to help answer questions and solve any needs that came up during our stay. The home is an extraordinary gem, located a few blocks from the lakefront. The architecture, large front porch and peaceful garden, including a gentle waterfall are all that is needed to refresh your spirit and keep you coming back!"
United States
Angela F.
LUXE Manor with Modern, Elegant Vibes

REMODELED HOME ON LAKE MICHIGAN

Sheboygan
9.8 out of 10, Exceptional, (159)
"Great property with an incredible view. Very close to excellent restaurants. We enjoyed the stay! "
United States
Kelly R.
REMODELED HOME ON LAKE MICHIGAN

Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Sheboygan
9.8 out of 10, Exceptional, (12)
"The location & accommodations were excellent. Communication with the property manager was easy. Would like to stay here again."
United States
Paul C.
Sheboygan Getaway w/ Yard: 1 Mi to Lake Michigan

Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan

Ellis Historical District
9.6 out of 10, Exceptional, (4)
"Great location right across from the Yacht Club. Was in town for a wedding. Perfect place to stay for the weekend. "
United States
Gary
Charming 2-bedroom condo with WiFi, AC in quaint Sheboygan

Lakeview Farm | Beach · Hot Tub · Theater · Views

Sheboygan
10.0 out of 10, Exceptional, (1)
"Fun time! Very buggy by the lake but not much you can do about that. "
United States
Jeff N.
Lakeview Farm | Beach · Hot Tub · Theater · Views

Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!

Downtown Sheboygan
9.8 out of 10, Exceptional, (9)
"The flat is gorgeous and in a fantastic location. "
United States
Sarah G.
The price is €260
includes taxes & fees
11 Nov - 12 Nov
Quaint Blast from the Past - Walk to Lake Michigan, Riverwalk and 8th St Shops!
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

Find out more about Sheboygan

Everything you need to know about Sheboygan holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Sheboygan holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Sheboygan holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Sheboygan holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Sheboygan holiday rentals we have selected for you start as low as €117 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Sheboygan rentals

At Expedia, we put the best Sheboygan holiday 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 holiday.

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. 

Frequently asked questions

Can I find a holiday rental in Sheboygan?

Yes, there are holiday rentals in Sheboygan close to Blue Harbor Resort & Conference Center Water Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Sheboygan speak positively about the popular beaches 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 holiday rentals that Sheboygan has to offer?

Lake Michigan Home with gorgeous views, great spot for family or golf retreat: This highly rated holiday home rental in Sheboygan is located on a lake, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Our travellers also rate Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host! as a favourite home for rent in Sheboygan.

How many holiday rentals will I find in Sheboygan?

Choose from 96 Expedia holiday rentals in Sheboygan for a memorable holiday.

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 holiday rental in Sheboygan like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Sheboygan. Holiday rentals provide amenities like laundry facilities and kitchens so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental an attractive option for a family trip.