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Sheboygan Holiday Rentals

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Holiday Rentals in Sheboygan

Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

10.0 out of 10, Exceptional, (1)
"Perfectly positioned! 5 minute drive or 15 minute walk from everything downtown. Quiet and relaxing, wonderful hosts!"
The price is AU$316
includes taxes & fees
25 June - 26 June
Coastal 3-BR Lower Near Lake MI and Downtown Sheboygan

Apartment Centrally Located

The price is AU$305
includes taxes & fees
25 June - 26 June
Apartment Centrally Located

Gleason's Chouse

10.0 out of 10, Exceptional, (35)
"This ‘chouse’ is so unique! Lovingly restored and beautifully decorated. Exceptional cleanliness and care for the comfort and enjoyment of their guests. We look forward to returning!"
The price is AU$302
includes taxes & fees
8 July - 9 July
Gleason's Chouse

Wyatt's Country Home - King Bed!

10.0 out of 10, Exceptional, (15)
"Beautiful property and perfect location!"
The price is AU$392
includes taxes & fees
14 July - 15 July
Wyatt's Country Home - King Bed!

Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

The price is AU$384
includes taxes & fees
15 July - 16 July
Eclectic 3-BR Lower w King Bed & Pack-n-Play & Fire Pit near Lake MI

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

10.0 out of 10, Exceptional, (105)
"This place is very clean and comfortable.The staff is very kindness. "
The price is AU$413
includes taxes & fees
20 July - 21 July
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.

The Esker Ridge Chalet, Pristine Elkhart Solitude

10.0 out of 10, Exceptional, (52)
"We loved our short stay at the Chalet--the hosts are friendly and polite, the space is well-equipped, and the beautiful Wisconsin woods surrounding us made for a tranquil winter holiday. We would highly recommend a visit!"
The price is AU$429
includes taxes & fees
8 July - 9 July
The Esker Ridge Chalet, Pristine Elkhart Solitude

Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

10.0 out of 10, Exceptional, (1)
"4 forever friends getaway. Relaxation, eats and drinks with a little antique and thrift shopping"
The price is AU$448
includes taxes & fees
26 June - 27 June
Eclectic Spacious 3 BR Home Near Lake MI w/ Fire Pit

New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

10.0 out of 10, Exceptional, (25)
"Every thing was great. "
The price is AU$548
includes taxes & fees
2 July - 3 July
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!

9 Mi to Shore: Home w/ Hot Tub in Howards Grove!

The price is AU$481
includes taxes & fees
26 June - 27 June
9 Mi to Shore: Home w/ Hot Tub in Howards Grove!

Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger

10.0 out of 10, Exceptional, (31)
"Awesome place. "
The price is AU$702
includes taxes & fees
25 June - 26 June
Private, Spacious Property, Hot Tub, Sleeps 9, EV Charger

4 Bedroom Home on the River with Private River access

9.8 out of 10, Exceptional, (27)
"This home has a calming vibe, and we felt very relaxed and at home while we stayed. The beds and pillows were so comfortable, and the showers had great water pressure. Good location to shop and eat local or day trips to neighboring towns. "
The price is AU$738
includes taxes & fees
26 June - 27 June
4 Bedroom Home on the River with Private River access

Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

10.0 out of 10, Exceptional, (168)
"We really enjoyed our stay. Clean, comfortable and a great location. The only nit I would have is the wifi is a little spotty, otherwise it was great!"
The price is AU$522
includes taxes & fees
6 July - 7 July
Cozy Cottage near Schwarz Supper Club, Road America, and Whistling Straights!!

Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

9.8 out of 10, Exceptional, (146)
"We had such an amazing time staying here and Rosalee was so accommodating throughout our stay!"
The price is AU$774
includes taxes & fees
25 June - 26 June
Lake Michigan views! Complimentary housekeeping with monthly stays Mar-Apr.

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

10.0 out of 10, Exceptional, (30)
"Perfect entertaining spot for a girls birthday weekend. The house is beautifully and perfectly appointed. A warm weather visit where we could enjoy the spacious fenced yard and walk to the lake may be in order. Great locatio just minutes from everything. "
The price is AU$875
includes taxes & fees
20 July - 21 July
The Suncatcher- Steps to Lake Michigan. Pet Friendly & Fully Fenced

Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

9.8 out of 10, Exceptional, (27)
"This is our 4th year staying at this great property!"
The price is AU$754
includes taxes & fees
30 June - 1 July
Behnke's Country Center, Reedsville WI. EAA, Green Bay Packers, Road America

Gorgeous private home hidden in the woods. Can sleep 11 guests

10.0 out of 10, Exceptional, (9)
"This VRBO was everything that the listing described and more. The host was very easy to communicate with and helped make sure we had a great stay."
The price is AU$1,146
includes taxes & fees
30 June - 1 July
Gorgeous private home hidden in the woods. Can sleep 11 guests

Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

4.0 star property
10.0 out of 10, Exceptional, (1)
"Our large family had a magical Christmas! Our beautifully decorated rented home had everything we needed . We were all very comfortable during the day and night time sleeping . We had private spaces and family get together areas ."
The price is AU$5,048
includes taxes & fees
7 July - 8 July
Best House in Wisconsin! Live like a STAR! VRBO Luxury! Huge Bar & Movie Theater

Executive Beachfront Villa: Sleeps 8!

2.0 star property
9.0 out of 10, Wonderful, (2)
"The home was great. The location was great. It was perfect for a night up at blue Harbor area to enjoy the restaurants and coffee shops."
The price is AU$1,052
includes taxes & fees
8 July - 9 July
Executive Beachfront Villa: Sleeps 8!

Road America, Elkhart Lake!

The price is AU$698
includes taxes & fees
1 July - 2 July
Road America, Elkhart Lake!
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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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 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 holiday rentals that Sheboygan has to offer?

Cozy Lake Michigan Cottage Direct Lakefront Views of Lake Michigan Premier Host!: 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. Kitchen amenities include a dishwasher, a fridge and a stovetop. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other homes for rent in Sheboygan include NEW! Charming 3BR/2BA Lake House in the Woods of the desirable Black River area and Lake Michigan Home with gorgeous views, great spot for family or golf retreat.

How many holiday rentals will I find in Sheboygan?

Choose from 95 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.