Holiday Rentals in Sheboygan County

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Featured Holiday Rentals in Sheboygan County

Lobby
Grandstay Residential Suites Hotel - 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
18 Nov - 19 Nov
Grandstay Residential Suites Hotel - Sheboygan
Outdoor dining
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room

Oostburg
9.6 out of 10, Exceptional, (215)
"Great place for a family getaway on Lake Michigan!"
United States
julie d.
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Luxury Condo | Terrace/patio
Victorian Inn Elkhart Lake Wisconsin

Victorian Inn Elkhart Lake Wisconsin

4.0 star property
Elkhart Lake
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
United States
Deirdre
Victorian Inn Elkhart Lake Wisconsin
Fridge, microwave, oven, stovetop
Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!

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!
Fridge, microwave, oven, stovetop
Lake Michigan Home with gorgeous views, great spot for family or golf retreat

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
Fireplace, books
Beach front luxury spacious villa !

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 !
On the beach, sun-loungers
Eat, Drink and be Cozy at Beachdaze this winter!

Eat, Drink and be Cozy at Beachdaze this winter!

Oostburg
10.0 out of 10, Exceptional, (140)
"Excellent place to stay for a quiet weekend on Lake Michigan. Cassie and Sam were great hosts and extremely helpful with anything we needed. Will certainly be going back!"
United States
Riley C.
Eat, Drink and be Cozy at Beachdaze this winter!
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.

Oostburg
10.0 out of 10, Exceptional, (115)
"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.
The price is €141
includes taxes & fees
1 Dec - 2 Dec
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Marina
Sheboygan Waterfront 3 Bedroom 2.5 Bathroom Home

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
Property grounds
Winter's a good time to stay in & cuddle at Surfdaze

Winter's a good time to stay in & cuddle at Surfdaze

Oostburg
10.0 out of 10, Exceptional, (115)
"Had a wonderful stay at SurfDaze. This was our 3rd stay and I hope that we will be back next year! "
United States
Danielle M.
Winter's a good time to stay in & cuddle at Surfdaze
Exterior
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.

Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.

Sheboygan
10.0 out of 10, Exceptional, (83)
"The back yard is absolutely amazing, games and activities galore. The beach was clean and amazing. Easily accessed by kids ranging from 3-12."
United States
Lisa M.
Don’t be a turkey – Celebrate Thanksgiving with family all under one roof.
Fridge, microwave, oven, stovetop
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan

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
12 Dec - 13 Dec
Chic 1-bedroom apartment with WiFi, AC in fabulous Sheboygan
On the beach
Rare Find! Huge Beach & Luxe Woodsy Cabin

Rare Find! Huge Beach & Luxe Woodsy Cabin

Oostburg
10.0 out of 10, Exceptional, (89)
"Perfect house, location, amenities and fun for the whole family!"
United States
Christina N.
Rare Find! Huge Beach & Luxe Woodsy Cabin
Smart TV
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

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
12 Nov - 13 Nov
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan
Terrace/patio
Cozy Crystal Lakefront Cottage

Cozy Crystal Lakefront Cottage

3.0 star property
Plymouth
10.0 out of 10, Exceptional, (9)
"Absolutely beautiful cottage and lake! The cottage is spacious, clean and includes all the amenities specified in the listing. There is plenty to do for all ages- kayaking, paddle boarding, floating pad and inflatable dock for lake, yard games, board games, relaxing in the hammock, reading in the screened in porch, smores by the campfire and enjoying the gorgeous sunsets. Pete was great with communicating check-in and check-out procedures and provided all necessary contact information. The...
United States
Wendy B.
Cozy Crystal Lakefront Cottage
Exterior
Edgewater Escape: 4 Bedroom, Sleeps 14!

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
12 Dec - 13 Dec
Edgewater Escape: 4 Bedroom, Sleeps 14!
Interior
BEACHSIDE GETAWAY IN SHEBOYGAN

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
Fridge, microwave, oven, stovetop
Baronwood Oasis-Indoor Pool/Spa-Arcades-16beds-LUX

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

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
Property grounds
tranquil cabin on 5 private acres w/ hot tub and sauna

tranquil cabin on 5 private acres w/ hot tub and sauna

Cascade
10.0 out of 10, Exceptional, (10)
"We loved this home and the location. The hot tub and sauna were great additions and all the nearby businesses they recommended were also great stops with awesome drinks and food. This was a great way to spend our 20th Wedding Anniversary !!"
United States
Laura N.
tranquil cabin on 5 private acres w/ hot tub and sauna
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sheboygan County Hotel Reviews

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Great service!"
Tyler 1-night trip
Posted 1 day ago
Watershed Hotel

Find out more about Sheboygan County

Holiday Homes in Sheboygan County

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

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

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