Entire home

Windward House - Entire home in Sheboygan

Photo gallery for Windward House - Entire home in Sheboygan

A living room with a fireplace, a sofa, a chair, a coffee table, a lamp, and a television.
A two-story house with a front porch, a small garden, and a tree.
A two-story stone house with a garage, a stone pathway, and a small garden.
A brick building with a white door, number 305, a porch with wicker furniture, and a bench.
A hallway with a bench, a door, and a window with blinds.

Highlights

  • Discover nearby landmarks
    Near John Michael Kohler Arts Center
2+ bathroomsSleeps 6

Popular amenities

  • Balcony
  • Air conditioning
  • Refrigerator
  • Washer
  • Onsite parking available
  • Fireplace

Explore the area

View in a map
Sheboygan, WI
  • Place, Deland Park
    ‪1 min walk‬
  • Place, John Michael Kohler Arts Center
    ‪7 min walk‬
  • Place, Blue Harbor Resort & Conference Center Water Park
    ‪5 min drive‬

Rooms & beds

0 bedrooms (sleeps 6)

Common Spaces

2 Queen Beds and 1 Double Bed

2 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Kitchen
Balcony
Garden

About this property

Windward House - Entire home in Sheboygan

Just steps from the Sheboygan Yacht Club and beautiful Deland Park with its sandy beach. This charming brick getaway puts you in the perfect location to enjoy beach days, lakefront sunsets, and all that Sheboygan has to offer. Stroll just four blocks to downtown to discover local restaurants, coffee shops, boutiques and nightlife. This inviting 3-bedroom, 2.5-bath home features comfortable living spaces and an adorable backyard perfect for relaxing after a day at the beach or exploring the city.

Layout
Bedroom 1: Queen located on the second level
Bedroom 2: Queen located on the second level
Bedroom 3: Full located on the second level
Bathroom 1: Half bathroom - located on main level in main entrance
Bathroom 2: Tub/Shower – located on the second level
Bathroom 3: Walk-in Shower – located in the basement off of laundry room
Laundry – detergent, dryer sheets, iron, ironing board provided - located in the basement

Amenities
Parking – 2 in driveway and additional street parking across from the home.
Outside Seating – located in fenced in backyard
WIFI – Included
HVAC - Forced air heat and central cooling
Fireplace – gas located on main level
Basics - Towels, shampoo, condition, body wash, hand soap and linens provided
Coffee –Ground coffee, drip coffee maker, creamer, sugar and to-go cups
Kitchen - Dish soap, dishwasher pods, cooking supplies
Dining Area – table for 4
TV – Roku tv’s located in living room, lower level living room and one queen bedroom
Extra – bar/family room located on lower level
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 5325626
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room

About the neighborhood

Sheboygan

Located near the beach, this vacation home is in Ellis Historical District, a neighborhood in Sheboygan. John Michael Kohler Arts Center and Sheboygan County Historical Museum are cultural highlights, and some of the area's attractions include Blue Harbor Resort & Conference Center Water Park and Stefanie H. Weill Center for the Performing Arts. Above & Beyond Children's Museum and Bookworm Gardens are also worth visiting.
Map
Sheboygan, WI

What's nearby

  • Deland Park - 1 min walk - 0.1 km
  • John Michael Kohler Arts Center - 7 min walk - 0.6 km
  • North Side Municipal Beach - 8 min walk - 0.7 km
  • Stefanie H. Weill Center for the Performing Arts - 10 min walk - 0.9 km
  • Blue Harbor Resort & Conference Center Water Park - 5 min drive - 2.5 km

Getting around

  • General Mitchell Intl. Airport (MKE) - 72 min drive

Restaurants

  • ‪Sheboygan YMCA - ‬4 min walk
  • ‪Umi Sushi - ‬11 min walk
  • ‪4th St Tap - ‬4 min walk
  • ‪Parker John's BBQ & Pizza - ‬12 min walk
  • ‪Tochi Ramen - ‬11 min walk

Frequently asked questions

Is Windward House - Entire home in Sheboygan pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Windward House - Entire home in Sheboygan?

As of Jun 20, 2026, prices found for a 1-night stay for 2 adults at Windward House - Entire home in Sheboygan on Jun 22, 2026 start from $497, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Windward House - Entire home in Sheboygan?

Check-in begins at 4:00 PM.

What time is check-out at Windward House - Entire home in Sheboygan?

Check-out is at 11:00 AM.

Where is Windward House - Entire home in Sheboygan located?

Located in Ellis Historical District, this vacation home is within a 5-minute walk of Deland Park and Lake Michigan. North Side Municipal Beach and John Michael Kohler Arts Center are also within 10 minutes.

About the host

Hosted by Ashley Little

Host profile image

Languages:

English
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