Sheboygan Vacation Rentals

05/22/2026

Our 7 bedroom, Sleeps 18, “Big Montana at Elkhart Lodge” received a serious update this Spring.

05/18/2026

Every year we look forward to the car parades and welcome parties that bring the streets of downtown Elkhart Lake to life. Mark your calendars for these summer favorites!

May 30 | The Hard Left Moto Show
June 18 | IndyCar Elkhart Lake Welcome Party
July 17 | Vintage Weekend Racecar Concours d'Elegance & Parade
July 18 | Vintage Weekend Sportscar Concours d'Elegance
July 30 | IMSA Welcome Party
August 27 | GT World Challenge Parade & Welcome Party

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05/13/2026

04/25/2026

04/10/2026

Please join us in welcoming Pine Beach Retreat in Oostburg to the Sheboygan Vacation Rentals family.

This 5 bedroom, 4 bathroom lakeside home truly embodies the "Malibu of the Midwest" vibe 🏄. Look out these windows and you just may feel like you are in Southern Cal.

www.sheboyganvacationrentals.com/pine-beach-retreat

www.airbnb.com/h/pinebeachoostburg

04/10/2026

For some homes it's a ... "Please let me introduce myself!"

Say hi to The Beach House .

Tucked up against the shores of Lake Michigan in Two Rivers, this stunner of a home abuts the beautiful Point Beach State Park allowing for literal miles of sandy beaches to traverse.

Professionally designed, this 5 bedroom, 3 bathroom, SLEEPS 20, lakeside home is built for your vacation. Every detail thought of when it comes to entertaining your friends, your children, or your in-laws.

Game Room ✅
Hot Tub ✅
Fire Pit ✅
5-Star Finishes ✅
Multiple Dining Tables ✅
Several Living Rooms ✅

This place literally has it all and no stone has been left unturned.

Learn more and book at www.manitowocvacationrentals.com

03/13/2026

Welcome Villa von Baumbach to the Sheboygan Vacation Rentals family.

Located directly on the ever desirable, Elkhart Lake, and listed on the National Register of Historic Places, this stunningly original home was built in 1894, and moved across the frozen lake in 1908.

Meticulously preserved, yet modernized, it boasts six bedrooms, three bathrooms and sleeps up to twelve people with eleven beds.

Do not miss the opportunity to live like "yester-year" and enjoy the pristine and clean deep waters of Elkhart Lake.

12/22/2025

Our guests over the holidays can be so fun ... and talented.
Grateful to be able to provide such lovely spaces to celebrate with friends and family.

12/20/2025

Ya just never know who you’ll run into at Pine Dunes Cabin. 🦌