House in Sheboygan, WI
14 guests · 5 bedrooms · 3 baths
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About this house rental
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 couple-friendly bedrooms, a six-person group room and two optional 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 finish the day with air hockey, arcade games or a fire overlooking the water.
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 full bathrooms and 1 half bathroom
• 2 king bedrooms and 2 queen bedrooms
• Group bedroom with 2 full beds and 2 twins in a trundle setup
• 8 fixed beds plus 2 optional twin rollaways
• Up to 10 sleeping surfaces within the 14-guest maximum
• 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
• Parking for up to 6 vehicles, including 2 garage spaces
• Approximately 20 minutes from Whistling Straits, Blackwolf Run and Kohler
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 features a large island, bar seating, gas range, generous preparation space and 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 for group breakfasts, holiday dinners and late-night conversations.
Bedroom 2 is located on this level and includes a queen bed. A full bathroom with a walk-in shower is directly across the hall. Guest laundry is also available on the main level.
PRIMARY LAKE-VIEW SUITE
Bedroom 1 is the upper-level primary suite—a private retreat within the larger group home.
Primary-suite features include:
• King bed
• Twin rollaway stored in the closet
• Vaulted ceiling
• Panoramic Lake Michigan windows and sunrise views
• Television
• Fireplace shared between the bedroom and bathroom
• Private coffee and beverage station with sink and undercounter refrigerator
The spa-style ensuite 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 UPPER-LEVEL BEDROOMS
Bedroom 3 includes a queen bed.
Bedroom 4 includes a king bed and a twin rollaway stored in the closet. A full bathroom is directly across the hall.
Bedroom 5 is the group room, with 2 full beds and 2 twins in a trundle setup. It sleeps up to 6 and works well for children, teens, families or friends.
A nearby reading loft provides a quieter place for coffee, conversation, reading or remote work.
SLEEPING ARRANGEMENTS
Bedroom 1 — Upper-level primary suite
• King bed
• Twin rollaway stored in closet
• Lake views, fireplace, beverage station and private ensuite
Bedroom 2 — Main level
• Queen bed
• Full bathroom directly across the hall
Bedroom 3 — Upper level
• Queen bed
Bedroom 4 — Upper level
• King bed
• Twin rollaway stored in closet
• Full bathroom directly across the hall
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
• 8 fixed beds and up to 10 sleeping surfaces
• Maximum occupancy: 14 registered guests
The rollaways add flexibility but do not increase the 14-guest maximum.
BATHROOMS
Captain’s Quarters has 3 full bathrooms and 1 half bathroom:
• Private primary ensuite with soaking tub and oversized walk-in shower
• Main-level full bathroom directly across from Bedroom 2
• Upper-level full bathroom directly across from Bedroom 4
• Additional half bathroom for group convenience
LOWER-LEVEL GAME ROOM
The lower level provides a separate entertainment space with air hockey, an arcade game, a television lounge and comfortable seating.
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, close to dining, breweries, shopping, groceries, golf and 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.
A vehicle is recommended. Drive times are approximate, and rideshare availability may be limited during high-demand golf or event weekends.
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.
PARKING AND ACCESS
Parking is available for up to 6 vehicles total:
• 2 vehicles may park inside the garage
• Remaining vehicles must park in the driveway
• Overnight street parking is not permitted
Guests have private use of the guest-accessible spaces and outdoor areas shown in the listing, including two garage parking spaces. Self-check-in is provided. Designated owner closets and basement utility areas remain locked.
IMPORTANT DETAILS
• Maximum occupancy is 14 registered overnight guests
• Two twin rollaways add flexibility but do not increase occupancy
• The home and shoreline are not step-free or represented as wheelchair accessible
• Four of the five 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 and utility areas are not accessible to guests
THE WISCONSIN GETAWAYS STANDARD
Captain’s Quarters is part of Wisconsin Getaways’ hand-selected collection of distinctive homes created for memorable group stays. Your reservation is supported by professional cleaning and preparation, responsive communication, clear arrival information, self-check-in, local hospitality support and professional maintenance resources.
The home offers a private, self-guided stay. The Wisconsin Getaways team is available before and during your visit for questions, recommendations and assistance. We respect your privacy and will not be onsite unless requested or required to address a property concern.
BOOK YOUR STAY
Wake to sunrise over the water, share unhurried meals and use the four private bedrooms, 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.
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 couple-friendly bedrooms, a six-person group room and two optional 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 finish the day with air hockey, arcade games or a fire overlooking the water.
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 full bathrooms and 1 half bathroom
• 2 king bedrooms and 2 queen bedrooms
• Group bedroom with 2 full beds and 2 twins in a trundle setup
• 8 fixed beds plus 2 optional twin rollaways
• Up to 10 sleeping surfaces within the 14-guest maximum
• 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
• Parking for up to 6 vehicles, including 2 garage spaces
• Approximately 20 minutes from Whistling Straits, Blackwolf Run and Kohler
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 features a large island, bar seating, gas range, generous preparation space and 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 for group breakfasts, holiday dinners and late-night conversations.
Bedroom 2 is located on this level and includes a queen bed. A full bathroom with a walk-in shower is directly across the hall. Guest laundry is also available on the main level.
PRIMARY LAKE-VIEW SUITE
Bedroom 1 is the upper-level primary suite—a private retreat within the larger group home.
Primary-suite features include:
• King bed
• Twin rollaway stored in the closet
• Vaulted ceiling
• Panoramic Lake Michigan windows and sunrise views
• Television
• Fireplace shared between the bedroom and bathroom
• Private coffee and beverage station with sink and undercounter refrigerator
The spa-style ensuite 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 UPPER-LEVEL BEDROOMS
Bedroom 3 includes a queen bed.
Bedroom 4 includes a king bed and a twin rollaway stored in the closet. A full bathroom is directly across the hall.
Bedroom 5 is the group room, with 2 full beds and 2 twins in a trundle setup. It sleeps up to 6 and works well for children, teens, families or friends.
A nearby reading loft provides a quieter place for coffee, conversation, reading or remote work.
SLEEPING ARRANGEMENTS
Bedroom 1 — Upper-level primary suite
• King bed
• Twin rollaway stored in closet
• Lake views, fireplace, beverage station and private ensuite
Bedroom 2 — Main level
• Queen bed
• Full bathroom directly across the hall
Bedroom 3 — Upper level
• Queen bed
Bedroom 4 — Upper level
• King bed
• Twin rollaway stored in closet
• Full bathroom directly across the hall
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
• 8 fixed beds and up to 10 sleeping surfaces
• Maximum occupancy: 14 registered guests
The rollaways add flexibility but do not increase the 14-guest maximum.
BATHROOMS
Captain’s Quarters has 3 full bathrooms and 1 half bathroom:
• Private primary ensuite with soaking tub and oversized walk-in shower
• Main-level full bathroom directly across from Bedroom 2
• Upper-level full bathroom directly across from Bedroom 4
• Additional half bathroom for group convenience
LOWER-LEVEL GAME ROOM
The lower level provides a separate entertainment space with air hockey, an arcade game, a television lounge and comfortable seating.
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, close to dining, breweries, shopping, groceries, golf and 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.
A vehicle is recommended. Drive times are approximate, and rideshare availability may be limited during high-demand golf or event weekends.
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.
PARKING AND ACCESS
Parking is available for up to 6 vehicles total:
• 2 vehicles may park inside the garage
• Remaining vehicles must park in the driveway
• Overnight street parking is not permitted
Guests have private use of the guest-accessible spaces and outdoor areas shown in the listing, including two garage parking spaces. Self-check-in is provided. Designated owner closets and basement utility areas remain locked.
IMPORTANT DETAILS
• Maximum occupancy is 14 registered overnight guests
• Two twin rollaways add flexibility but do not increase occupancy
• The home and shoreline are not step-free or represented as wheelchair accessible
• Four of the five 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 and utility areas are not accessible to guests
THE WISCONSIN GETAWAYS STANDARD
Captain’s Quarters is part of Wisconsin Getaways’ hand-selected collection of distinctive homes created for memorable group stays. Your reservation is supported by professional cleaning and preparation, responsive communication, clear arrival information, self-check-in, local hospitality support and professional maintenance resources.
The home offers a private, self-guided stay. The Wisconsin Getaways team is available before and during your visit for questions, recommendations and assistance. We respect your privacy and will not be onsite unless requested or required to address a property concern.
BOOK YOUR STAY
Wake to sunrise over the water, share unhurried meals and use the four private bedrooms, 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.
Amenities at Captain`s Quarters | Lake Michigan views for 14
Non-smoking
No pets allowed
Family friendly
Map of Sheboygan, WI
$$$$
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