Captain`s Quarters | Lake Michigan views for 14 | House in Sheboygan

CAPTAIN’S QUARTERS: LAKE MICHIGAN GROUP RETREAT
Wake to panoramic Lake Michigan sunrises at Captain’s Quarters, a refined 5-bedroom, 3.5-bath retreat for up to 14 guests in Sheboygan near Kohler and championship golf.
Across approximately 3,375 square feet, the home combines four private adult bedrooms, a flexible six-person group room and two twin rollaways. Gather in the lake-view living room and kitchen, unwind in the spa-style primary suite, enjoy drinks at the outdoor bar, then end the day with air hockey, arcade games or a fire beside the lake.
Professionally managed by Wisconsin Getaways, Captain’s Quarters offers the privacy of a whole-home stay with professional preparation, responsive communication and local support.
WHY GROUPS CHOOSE CAPTAIN’S QUARTERS
• Panoramic Lake Michigan views and sunrise over the water
• 5 bedrooms, 3.5 bathrooms and space for up to 14 guests
• 2 king bedrooms and 2 queen bedrooms for couples and adults
• Group bedroom with 2 full beds and 2 twins in a trundle setup
• 2 additional twin rollaways for flexible sleeping
• Spa-style primary suite with soaking tub, fireplace and lake view
• Open lake-view kitchen, dining and living spaces
• Outdoor bar, patio dining, gas grill and wood-burning firepit
• Air hockey, arcade game and separate TV lounge
• Reading loft and multiple places for the group to spread out
• Approximately 20 minutes from Whistling Straits, Blackwolf Run and Kohler
• Convenient access to downtown Sheboygan and Road America
THE MAIN GATHERING LEVEL
The lake-view living room is the social heart of the home. Panoramic windows frame Lake Michigan, while comfortable seating, a fireplace and large television create an inviting place to reconnect after golf, sightseeing or a day in Sheboygan.
The open kitchen keeps cooks in the center of the experience with a large island, bar seating, gas range, generous preparation space and an easy flow into the dining and living areas. A separate beverage station includes a sink and undercounter refrigerator.
The dining area connects the kitchen with the lake-facing outdoor spaces, making it equally comfortable for golf-trip breakfasts, holiday dinners, birthday meals and late-night conversations.
Bedroom 1 is located on the main level and includes a king bed. A twin rollaway is stored in the closet. A full bathroom with a walk-in shower is directly across the hall. Guest laundry is also located on this level.
THE PRIMARY LAKE-VIEW SUITE
The upper-level primary suite is a private retreat within the larger group home.
Features include:
• King bed
• Vaulted ceiling
• Panoramic Lake Michigan windows
• Direct sunrise views
• Television
• Fireplace shared between the bedroom and bathroom
• Private coffee and beverage station
• Sink and undercounter beverage refrigerator
• Twin rollaway stored in the closet
The ensuite bathroom includes a freestanding soaking tub beside the fireplace, Lake Michigan views, an oversized walk-in shower with multiple showerheads, two separate vanities and a private water closet.
ADDITIONAL BEDROOMS AND SLEEPING
Two additional upper-level bedrooms each include a queen bed, giving couples, parents and adult guests private rooms of their own.
The fifth bedroom is designed for families and shared groups, with 2 full beds and 2 twins in a trundle setup. It sleeps up to 6 and works especially well for children, teens, cousins, siblings or friends.
A shared full bathroom serves the additional upper-level bedrooms. The nearby reading loft provides a quiet place for coffee, conversation, reading or remote work.
SLEEPING ARRANGEMENTS
Bedroom 1 — Main level
• King bed
• Twin rollaway stored in closet
• Full bathroom directly across the hall
Bedroom 2 — Upper level
• Queen bed
Bedroom 3 — Upper level
• Queen bed
Bedroom 4 — Upper-level primary suite
• King bed
• Twin rollaway stored in closet
• Lake views, fireplace and private ensuite
Bedroom 5 — Upper-level group bedroom
• 2 full beds
• 2 twins in a trundle setup
• Sleeps up to 6
Bed count:
• 2 king beds
• 2 queen beds
• 2 full beds
• 2 trundle twin beds
• 2 twin rollaway beds
• Up to 10 sleeping surfaces
• Maximum occupancy: 14 registered guests
The rollaways provide flexibility but do not increase the 14-guest maximum.
BATHROOMS
Captain’s Quarters has 3 full bathrooms and 1 half bathroom, including:
• Primary ensuite with soaking tub and oversized walk-in shower
• Main-level full bathroom with walk-in shower
• Upper-level shared full bathroom
• Additional half bathroom for group convenience
LOWER-LEVEL GAME ROOM
The lower level provides a separate entertainment space with:
• Air hockey table
• Arcade game
• Television lounge
• Comfortable seating
• Open space for casual group time
OUTDOOR EXPERIENCE
The bluff-top outdoor spaces are centered on the Lake Michigan view.
Start the morning in an Adirondack chair as the sun rises over the water. Play cornhole on the lawn, gather for drinks at the outdoor bar, share dinner outside and finish the evening around the wood-burning firepit.
Outdoor features include:
• Panoramic Lake Michigan views
• Broad lake-facing lawn
• Outdoor bar with seating
• Patio dining area
• LP gas grill with propane provided
• Wood-burning firepit
• Swing and additional firepit seating
• Cornhole
• Adirondack and lounge seating
Firewood is not provided.
SHEBOYGAN, KOHLER AND AREA ATTRACTIONS
Captain’s Quarters is located in a residential Lake Michigan neighborhood in the City of Sheboygan. The setting offers peaceful lakeside mornings while keeping your group close to dining, breweries, shopping, groceries, golf and major regional attractions.
Approximate drive times:
• Downtown Sheboygan and its waterfront district — 10 minutes
• Whistling Straits — 20 minutes
• Blackwolf Run — 20 minutes
• Village of Kohler and The American Club — 20 minutes
• Road America — 35–40 minutes
Golf groups can play championship courses during the day, then return to a private home where everyone can gather. Downtown Sheboygan offers dining, breweries, shopping and waterfront attractions, while Kohler adds destination dining, spa experiences and additional golf.
Drive times are approximate. A vehicle is recommended, and rideshare availability may be limited during high-demand periods.
IMPORTANT WATERFRONT INFORMATION
Captain’s Quarters is a bluff-top, view-first waterfront property—not a beach property.
There is no sand beach, dock or pier. The shoreline below the home consists of massive boulders. Reaching it requires a long, steep exterior staircase followed by difficult, uneven terrain.
There is no easy swimming entry or convenient place to launch kayaks, paddleboards or other watercraft. Access is not step-free, and wind, waves, water levels and seasonal conditions can make the shoreline more difficult to reach.
Children require close adult supervision near the bluff, stairs and water. Book this home for its panoramic views, sunrise, Lake Michigan atmosphere and outdoor gathering spaces rather than convenient water recreation.
IMPORTANT DETAILS
• Maximum occupancy is 14 registered overnight guests
• Two twin rollaways add flexibility but do not increase occupancy
• Parking is limited to 4 vehicles in the driveway
• No street parking or guest access to the garage
• The home and shoreline are not step-free or represented as wheelchair accessible
• Most bedrooms require interior stairs
• Neighboring homes are visible on both sides
• Quiet hours must be respected in this residential setting
• Celebratory stays are welcome, but parties and events are not permitted
• No outdoor amplified music or disruptive noise
• No pets except as required by applicable law
• No smoking or vaping indoors
• Propane is provided for the grill; firewood is not provided
• Designated owner closets, garage and utility areas are not accessible to guests
Guests have private use of all guest-accessible indoor and outdoor areas shown in the listing. Self-check-in is provided.
Captain’s Quarters offers a private, self-guided stay. The Wisconsin Getaways team is available before and during your visit for questions, local recommendations and assistance when needed. We respect your privacy and will not be onsite unless requested or required to address a property concern.
BOOK YOUR STAY
Bring the people who matter most and make Captain’s Quarters the setting for a memorable Lake Michigan escape.
Wake to sunrise over the water, share unhurried meals, give couples and adults four private bedrooms, and use the group room and rollaways to customize sleeping for your stay. Whether you are planning a multi-family gathering, couples’ getaway, championship golf trip, leadership retreat, holiday or milestone weekend, Captain’s Quarters gives your group the space, setting and support to experience Wisconsin together.

Captain`s Quarters | Lake Michigan views for 14 is located in Sheboygan. Captain`s Quarters | Lake Michigan views for 14 provides accommodation, featuring Air Conditioner, TV, Security/Safety, among other amenities. This House features Air Conditioner, Parking and TV to make your stay a comfortable one.

Captain`s Quarters | Lake Michigan views for 14 has 1 Bedroom , 4 Bathrooms, and max occupancy of 14 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Sheboygan has interesting places to visit. If you want to learn more about the House in Sheboygan, such as places to visit and things to do nearby, you can check below to learn more.