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Check prices for these dates

In two weeks
5 Sept - 7 Sept
In two months
17 Oct - 19 Oct
In three months
14 Nov - 16 Nov
In four months
12 Dec - 14 Dec

Browse Select Sheboygan Holiday Homes

Our top choices for Sheboygan holiday homes

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, (202)
"The house is beautiful and the location can't be beat! "
Large Unique & Artistic Lake Michigan Beach House / Awesome Game Room
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
Fridge, microwave, oven, stovetop

Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau

10.0 out of 10, Exceptional, (64)
"It is to nice that you get to stay in a house this nice- the lake is there and with that the sunset. It is well-stocked and very clean. It is a great place to stay"
Large, cozy lake home near Round Lake Farm, Nordic Center, Road America, Lambeau
'Twilight' - Just a few steps down to Lake Winnebago!
Exterior

'Twilight' - Just a few steps down to Lake Winnebago!

10.0 out of 10, Exceptional, (19)
"Perfect place to stay during the EAA Oshkosh Airventure. Perfect area, nice place, great amenities."
'Twilight' - Just a few steps down to Lake Winnebago!
Lake Michigan Gem: Private Beach & Game Room
Lobby

Lake Michigan Gem: Private Beach & Game Room

9.8 out of 10, Exceptional, (6)
"The venure/location was perfect for our golf trip. Top notch everything and Michelle and Markus were really great to work with. Will definitely be back next time we are back for golf. Thanks again!"
Lake Michigan Gem: Private Beach & Game Room
East River Retreat, WATERFRONT+ Fire Pit+Pet friendly
Property grounds

East River Retreat, WATERFRONT+ Fire Pit+Pet friendly

9.2 out of 10, Wonderful, (52)
"The property and the host were amazing."
East River Retreat, WATERFRONT+ Fire Pit+Pet friendly
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, (107)
"Great place to hang out and relax. Everything was thought of, which made it easy to enjoy."
The price is £138
includes taxes & fees
11 Sept - 12 Sept
Tranquil Cottage in the Woods with Lake Michigan only 300 feet away.
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 £209
includes taxes & fees
2 Sept - 3 Sept
The Esker Ridge Chalet, Pristine Elkhart Solitude
Super clean amazing location downtown Elkhart Lake
TV

Super clean amazing location downtown Elkhart Lake

10.0 out of 10, Exceptional, (14)
"Will stay here again, when in the area, without a doubt."
Super clean amazing location downtown Elkhart Lake
Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown
Fridge, microwave, oven, stovetop

Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown

10.0 out of 10, Exceptional, (53)
"Nice property for a family to stay. Close to Lake Michigan and easy access to grocery stores and tourist attractions."
Brick Tudor Vacation Rental House Close To Lake Michigan And Downtown
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, (247)
"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!
Beach House- 3 blocks to beach, Huge patio, Sauna, Fire Pit and 2 bikes! 🚲🔥🌊
Interior

Beach House- 3 blocks to beach, Huge patio, Sauna, Fire Pit and 2 bikes! 🚲🔥🌊

9.8 out of 10, Exceptional, (39)
"Quick resposnes to questions before booking. Priced great and in a great neighborhood. Close to everything. Very comfortable and efficient."
Beach House- 3 blocks to beach, Huge patio, Sauna, Fire Pit and 2 bikes! 🚲🔥🌊
Private Beach on Lake Michigan: Oostburg Home
Property grounds

Private Beach on Lake Michigan: Oostburg Home

8.0 out of 10, Very good, (1)
"Adorable lake house with great views. We had an amazing girls weekend."
Private Beach on Lake Michigan: Oostburg Home
Beautiful Lake House on the Shores of Erler Lake.
Dining

Beautiful Lake House on the Shores of Erler Lake.

9.6 out of 10, Exceptional, (209)
"The home is cozy and spacious. It is in a park so the kids went fishing and walked the paths. It was still cold out so we didn’t use the beautiful beach area. Lake is very clear. I highly recommend staying here. "
Beautiful Lake House on the Shores of Erler Lake.
6 Bedroom house on 7 acres
Smart TV, fireplace

6 Bedroom house on 7 acres

9.8 out of 10, Exceptional, (34)
"8 adult golfers stayed here to play the Kohler courses. It worked out great for us. house was a perfect home away from home...provided great entertainment for post round activities"
6 Bedroom house on 7 acres
Experience Lake Michigan views from your cozy 3-bedroom retreat
Outdoor dining

Experience Lake Michigan views from your cozy 3-bedroom retreat

10.0 out of 10, Exceptional, (27)
"We loved this quiet and relaxing property. A short walk to the lake and short drive to great golf courses!"
Experience Lake Michigan views from your cozy 3-bedroom retreat
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
Property grounds

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

10.0 out of 10, Exceptional, (26)
"Every thing was great. "
The price is £253
includes taxes & fees
6 Sept - 7 Sept
New! Riverfront Retreat! Dock! Near downtown & Neshotah Park. Dogs ok!
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Fridge, microwave, oven, stovetop

New King Park Beach Lookout Deluxe! 3BR Right at Lake!

2.0 star property
10.0 out of 10, Exceptional, (8)
"It’s a gem—fabulous views of Lake Michigan and sand in your toes just across the street. Light and bright well appointed interior with anything you’ll need to enjoy your stay. Short walk to food and entertainment on the Harbor. Owner is very responsive."
New King Park Beach Lookout Deluxe! 3BR Right at Lake!
Charming 4 Bedroom Historic Home Centrally located in Northeastern Wisconsin
Exterior

Charming 4 Bedroom Historic Home Centrally located in Northeastern Wisconsin

10.0 out of 10, Exceptional, (5)
Charming 4 Bedroom Historic Home Centrally located in Northeastern Wisconsin
Family-Friendly House: Walk to Lake Michigan!
Fridge, microwave, stovetop, dishwasher

Family-Friendly House: Walk to Lake Michigan!

9.6 out of 10, Exceptional, (26)
"Very happy with the house we rented, it was very clean, well stocked, and great location. Definitely will recommend!"
Family-Friendly House: Walk to Lake Michigan!
Kettle Moraine Lake House, Private Family Friendly Lakehouse Retreat Sleeps 8
Fridge, microwave, oven, stovetop

Kettle Moraine Lake House, Private Family Friendly Lakehouse Retreat Sleeps 8

9.4 out of 10, Exceptional, (10)
"Great place, location and communication from the owner."
Kettle Moraine Lake House, Private Family Friendly Lakehouse Retreat Sleeps 8
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

Watershed Hotel

Watershed Hotel

10/10 Excellent
"Attractive contemporary architecture in room and facilities. "
Bernard 1-night trip
Posted 2 days ago
Watershed Hotel