Holiday Rentals in Sheboygan County

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Featured Holiday Rentals in Sheboygan County

Our top choices for Sheboygan County holiday 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 €111
includes taxes & fees
1 Oct - 2 Oct
Grandstay Residential Suites Hotel - Sheboygan
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Outdoor dining

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

9.6 out of 10, Exceptional, (207)
"The house is beautiful and the location can't be beat! "
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Victorian Inn Elkhart Lake Wisconsin
Luxury Condo | Terrace/patio

Victorian Inn Elkhart Lake Wisconsin

4.0 star property
8.8 out of 10, Excellent, (3)
"Perfect location, great amenities."
Victorian Inn Elkhart Lake Wisconsin
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 !
Fall dates available at SurfDaze!
Property grounds

Fall dates available at SurfDaze!

10.0 out of 10, Exceptional, (111)
"It was wonderful. Views were stunning. So close to the water. Very relaxing. Our family loved it."
Fall dates available at SurfDaze!
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 €114
includes taxes & fees
28 Sept - 29 Sept
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
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
Exterior

Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

10.0 out of 10, Exceptional, (108)
"Great place to hang out and relax. Everything was thought of, which made it easy to enjoy."
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
October Dates available!
On the beach, sun-loungers

October Dates available!

10.0 out of 10, Exceptional, (136)
"Great location and wonderful host. Would stay again!"
October Dates available!
Rare Find! Huge Beach & Luxe Woodsy Cabin
On the beach

Rare Find! Huge Beach & Luxe Woodsy Cabin

10.0 out of 10, Exceptional, (87)
"Property is very relaxing and host was super helpful and responsive. "
Rare Find! Huge Beach & Luxe Woodsy Cabin
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 €160
includes taxes & fees
7 Oct - 8 Oct
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
The Esker Ridge Chalet, Pristine Elkhart Solitude
Exterior

The Esker Ridge Chalet, Pristine Elkhart Solitude

10.0 out of 10, Exceptional, (58)
"Wonderful place, so quiet and nature surrounding the location. So close to Elkhart Lake and yet you wouldn't realize it when on the property. Five Stars!"
The price is €240
includes taxes & fees
30 Sept - 1 Oct
The Esker Ridge Chalet, Pristine Elkhart Solitude
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
Halloween on a Friday? Spooky opportunity to hunker down in an old mansion.
Exterior

Halloween on a Friday? Spooky opportunity to hunker down in an old mansion.

10.0 out of 10, Exceptional, (82)
"Great location"
Halloween on a Friday? Spooky opportunity to hunker down in an old mansion.
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Fridge, microwave, oven, stovetop

NEW Three bedroom ranch style pet friendly home with a patio & theatre room!

10.0 out of 10, Exceptional, (51)
"Great place and so quiet!!"
NEW Three bedroom ranch style pet friendly home with a patio & theatre room!
Lake House w/ 6-BR's, Sauna - Kohler-Andrae
On the beach

Lake House w/ 6-BR's, Sauna - Kohler-Andrae

10.0 out of 10, Exceptional, (17)
"We had an amazing stay at this property. It was very clean, big, and had everything we needed. The outdoor area and easy access to the beach was perfect! We would definitely love to come back."
Lake House w/ 6-BR's, Sauna - Kohler-Andrae
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 County 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 3 days ago
Harbor Winds Hotel

Find out more about Sheboygan County

Find out more about Sheboygan County

Holiday Homes in Sheboygan County

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