Captain’s Quarters
Sheboygan, WI
About this listing
Wake to panoramic Lake Michigan sunrises at Captain’s Quarters, a refined 5-bedroom retreat for up to 14 in Sheboygan near Kohler and championship golf. Four private bedrooms, a six-person group room and two twin rollaways offer up to 10 sleeping surfaces for flexible group stays. Gather in the lake-view living room and kitchen, unwind in the spa-style primary suite, then enjoy the outdoor bar, firepit, air hockey and arcade games.
The space
THE CAPTAIN’S QUARTERS EXPERIENCE
Captain’s Quarters is a refined Lake Michigan retreat designed for multi-family gatherings, golf trips, couples traveling together, holiday stays, milestone weekends and leadership retreats where everyone wants to stay under one roof without feeling crowded.
Across approximately 3,375 square feet, the home accommodates up to 14 guests in five bedrooms. Four couple-friendly bedrooms—two with king beds and two with queen beds—give couples, parents and adult guests private spaces of their own. A dedicated group bedroom with two full beds and two twins in a trundle setup sleeps up to six.
Two additional twin rollaway beds are stored in the Bedroom 1 and Bedroom 4 closets. These provide flexibility for groups whose guests prefer separate sleeping surfaces but do not increase the home’s maximum occupancy above 14.
Panoramic Lake Michigan views anchor the main gathering spaces, primary suite and bluff-top outdoor areas. Wake to sunrise over the water, gather around the kitchen island before a tee time, spend the day exploring Sheboygan or Kohler, then return for drinks at the outdoor bar, dinner from the grill, air hockey and arcade competition, or a long conversation around the firepit.
Professionally managed by Wisconsin Getaways, Captain’s Quarters combines the privacy of a whole-home stay with the preparation and support of an experienced Wisconsin hospitality team.
WHY GROUPS CHOOSE CAPTAIN’S QUARTERS
âś” Panoramic Lake Michigan views and sunrise directly over the water
âś” 5 bedrooms, 3 full bathrooms and 1 half bathroom
âś” 2 king bedrooms and 2 queen bedrooms
âś” Group bedroom with 2 full beds and 2 twins in a trundle setup
âś” 8 fixed beds plus 2 optional twin rollaways
âś” Up to 10 sleeping surfaces within the 14-guest maximum
âś” Spa-style primary suite with soaking tub, fireplace and lake view
âś” Open lake-view kitchen, dining and living spaces
âś” Outdoor bar, patio dining, gas grill and wood-burning firepit
âś” Air hockey, arcade game and separate television lounge
âś” Reading loft and multiple spaces where the group can spread out
âś” Parking for up to 6 vehicles, including 2 garage spaces
âś” Approximately 20 minutes from Whistling Straits, Blackwolf Run and Kohler
âś” Professional preparation and local support from Wisconsin Getaways
THE MAIN GATHERING LEVEL
The lake-view living room is the social heart of the home. Panoramic windows frame Lake Michigan while generous seating, a fireplace and large television create a comfortable place for everyone to reconnect after a day of golf, sightseeing or exploring Sheboygan.
The open gathering kitchen keeps cooks at the center of the experience rather than separated from the rest of the group.
Kitchen features include:
âś” Large island with bar seating
âś” Gas range
âś” Generous preparation and counter space
âś” Open flow into the living and dining areas
âś” Lake Michigan visible through the adjoining gathering spaces
âś” Separate beverage station with sink and undercounter refrigerator
The dining area sits between the kitchen and lake-facing outdoor spaces, creating an easy setting for golf-trip breakfasts, holiday dinners, birthday meals and late-night conversations.
Bedroom 2 is located on the main level and includes a queen bed. A full bathroom with a walk-in shower is located directly across the hall.
The main level also includes guest laundry, making the home practical for extended stays, active trips and larger groups.
THE PRIMARY LAKE-VIEW SUITE
Bedroom 1 is the upper-level primary suite—a private retreat within the larger group home.
Wake to Lake Michigan through the panoramic windows, make coffee without leaving the suite and enjoy a quiet start before the rest of the house comes together.
Primary-suite features include:
âś” King bed
âś” Twin rollaway stored in the closet
âś” Vaulted ceiling
âś” Panoramic Lake Michigan windows
âś” Direct sunrise views
âś” Television
âś” Fireplace shared between the bedroom and bathroom
âś” Private coffee and beverage station
âś” Sink and undercounter beverage refrigerator
The adjoining spa-style ensuite bathroom includes:
âś” Freestanding soaking tub beside the fireplace
âś” Lake Michigan view
âś” Oversized walk-in shower with multiple showerheads
âś” Two separate vanities
âś” Private water closet
It is an elevated couples’ retreat designed for slow mornings, post-golf recovery and quiet evenings away from the main gathering spaces.
ADDITIONAL UPPER-LEVEL BEDROOMS
Bedroom 3 includes a queen bed and provides another private room for a couple, parent or adult guest.
Bedroom 4 includes a king bed and a twin rollaway stored in the closet. A full bathroom is located directly across the hall.
Bedroom 5 is the upper-level group bedroom and includes:
âś” 2 full beds
âś” 2 twin beds in a trundle setup
âś” Sleeping space for up to 6 guests
The group room works particularly well for children, teens, cousins, siblings, families or friends who prefer a shared sleeping space.
The nearby reading loft provides another quiet place for coffee, conversation, reading or remote work.
SLEEPING ARRANGEMENTS
Bedroom 1 — Upper-level primary suite
âś” King bed
âś” Twin rollaway stored in the closet
âś” Panoramic Lake Michigan views
âś” Fireplace
âś” Private coffee and beverage station
âś” Spa-style ensuite bathroom
âś” King bed sleeps 2, with optional rollaway flexibility
Bedroom 2 — Main level
âś” Queen bed
âś” Full bathroom directly across the hall
âś” Sleeps 2
Bedroom 3 — Upper level
âś” Queen bed
âś” Sleeps 2
Bedroom 4 — Upper level
âś” King bed
âś” Twin rollaway stored in the closet
âś” Full bathroom directly across the hall
âś” King bed sleeps 2, with optional rollaway flexibility
Bedroom 5 — Upper-level group bedroom
âś” 2 full beds
âś” 2 twin beds in a trundle setup
âś” Sleeps up to 6
Bed count at a glance
âś” 2 king beds
âś” 2 queen beds
âś” 2 full beds
âś” 2 twin beds in a trundle setup
âś” 2 twin rollaway beds
âś” 8 fixed beds
âś” Up to 10 sleeping surfaces available
âś” Maximum occupancy of 14 registered guests
The rollaway beds provide optional sleeping flexibility within the 14-guest maximum. They are especially useful for mixed groups, families and golf trips where some guests prefer separate sleeping surfaces.
BATHROOMS
Captain’s Quarters has 3 full bathrooms and 1 half bathroom.
The bathroom layout includes:
âś” Private primary ensuite with soaking tub and oversized walk-in shower
âś” Main-level full bathroom directly across from Bedroom 2
âś” Upper-level full bathroom directly across from Bedroom 4
âś” Additional half bathroom for group convenience
âś” Two vanities and a private water closet in the primary ensuite
LOWER-LEVEL GAME ROOM
The lower-level game room gives part of the group somewhere more active to gather without taking over the main lake-view living room.
Features include:
âś” Air hockey table
âś” Arcade game
âś” Television lounge
âś” Comfortable seating
âś” Open space for casual group time
It is an easy evening destination for children, teens and competitive adults—and a useful second gathering zone when different parts of the group want different experiences.
OUTDOOR EXPERIENCE
The bluff-top outdoor spaces are designed around 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 firepit.
Outdoor features include:
âś” Panoramic Lake Michigan views
âś” Broad lake-facing lawn
âś” Wood-burning firepit
âś” Swing and additional firepit seating
âś” Outdoor bar with seating
âś” Patio dining area
âś” LP gas grill
âś” Propane provided for the grill
âś” Cornhole
âś” Adirondack and lounge seating
Firewood is not provided.
SHEBOYGAN, KOHLER AND CHAMPIONSHIP GOLF
Captain’s Quarters is located in the City of Sheboygan, offering a residential Lake Michigan setting while keeping the group close to the region’s strongest golf, dining and recreation destinations.
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 whole home where everyone can gather rather than separating into hotel rooms. The four couple-friendly bedrooms, group room and two rollaways also provide useful flexibility for mixed sleeping preferences.
Downtown Sheboygan offers restaurants, breweries, coffee shops, shopping, groceries and waterfront attractions. Kohler adds destination dining, spa experiences and additional golf, while Road America makes Captain’s Quarters a compelling home base for race weekends and driving events.
Drive times are approximate and may vary with traffic, weather and major regional events.
IMPORTANT WATERFRONT INFORMATION
Captain’s Quarters is a bluff-top, view-first waterfront property.
There is no sand beach, dock or pier. The shoreline below the property consists of massive boulders, and reaching it requires descending a long, steep outdoor staircase followed by difficult and uneven terrain.
There is no easy swimming entry or convenient place to launch kayaks, paddleboards or other watercraft. Access is not step-free, and waves, wind, water levels and seasonal conditions can make the shoreline more difficult to reach.
Children require close adult supervision near the bluff, exterior stairs and water.
The property is best suited to guests who value panoramic views, sunrise, Lake Michigan atmosphere and outdoor gathering spaces rather than convenient water recreation.
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:
âś” Professional cleaning and property preparation
âś” Responsive communication before and during your stay
âś” Clear arrival and property information
âś” Streamlined self-check-in
âś” Local hospitality and operational support
âś” Professional maintenance resources
âś” A team experienced in managing large-group vacation homes
You receive the space and privacy of a whole-home stay with the preparation, responsiveness and consistency of an established Wisconsin hospitality team.
IMPORTANT DETAILS
Please review these items before booking:
âś” Maximum occupancy is 14 registered overnight guests
âś” Two twin rollaways provide flexibility but do not increase occupancy
âś” Parking is limited to 6 vehicles total
âś” Two garage parking spaces are available
âś” Remaining vehicles must park in the driveway
âś” Overnight street parking is not permitted
âś” No beach, dock, pier or easy water entry
âś” Shoreline access involves a long staircase and massive boulders
âś” The home and shoreline are not step-free or represented as wheelchair accessible
âś” Four of the five bedrooms require interior stairs
âś” Neighboring homes are visible on both sides of the property
âś” This is a residential setting and quiet hours must be respected
âś” Celebratory stays are welcome, but parties and events are not permitted
âś” No outdoor amplified music or disruptive noise
âś” No pets except as required by applicable law or Airbnb policy
âś” No smoking or vaping indoors
âś” Propane is provided for the gas grill
âś” Firewood is not provided
âś” Designated owner closets and utility areas are not accessible to guests
Any required guest-verification or rental-agreement steps will be disclosed before booking and administered in accordance with Airbnb policy.
BOOK YOUR STAY
Bring the people who matter most and make Captain’s Quarters the setting for the kind of trip everyone remembers.
Wake to Lake Michigan sunrises, share unhurried meals and give couples, parents and adult guests four private bedrooms while children, relatives or friends settle into the flexible group room. Two additional twin rollaways make it easier to customize sleeping arrangements without increasing the home’s 14-person capacity.
Whether you are planning a multi-family gathering, couples’ getaway, championship golf trip, leadership retreat, holiday stay or milestone weekend, Captain’s Quarters gives your group the space, setting and support to experience Wisconsin together.
Guest access
Guests have private use of all guest-accessible indoor and outdoor areas shown in the listing, including:
âś” 5 bedrooms
âś” 3 full bathrooms and 1 half bathroom
âś” Living and dining spaces
âś” Kitchen and beverage station
âś” Reading loft
âś” Lower-level game room
âś” Guest laundry
âś” Lake-view lawn
âś” Patio and outdoor bar
âś” Firepit and grill area
âś” Driveway parking
âś” Two garage parking spaces
Self-check-in is provided through the home’s guest-access system.
Designated owner and operations closets and basement utility areas are locked and are not included in the rental.
Other things to note
Captain’s Quarters sits on a bluff above a rugged Lake Michigan shoreline. There is no beach, dock or pier. Reaching the water requires a long, steep exterior staircase followed by large boulders and uneven terrain.
The shoreline is not appropriate for guests seeking easy swimming, launching watercraft or step-free waterfront access. Natural Lake Michigan conditions—including wind, waves, colder temperatures and changing water levels—are part of the setting.
The home is located in a residential area with neighboring houses visible on both sides. Respectful outdoor use and quiet hours are required.
Parking is limited to 6 vehicles total. Two vehicles may park in the garage, with the remaining vehicles in the driveway. Overnight street parking is not permitted.
The home is not step-free and is not represented as wheelchair accessible. Interior stairs are required to reach four of the five bedrooms, and substantial exterior stairs are required to approach the shoreline.
Two twin rollaway beds are stored in the Bedroom 1 and Bedroom 4 closets. They provide optional sleeping flexibility within the home’s 14-guest maximum and do not increase permitted occupancy.
Details
- Guests: 14
- Bedrooms: 5
- Beds: 10
- Bathrooms: 3
- Check-in After: 04:00 PM
- Check-out Before: 10:00 AM
- Type: House
Prices
- per night: $600
- Allow additional guests: No
- Cleaning fee: $384
Features
Amenities
- Air conditioning
- Baking sheet
- Barbeque utensils
- Bartender on request
- Body soap
- Car recommended
- Carbon Monoxide Detector
- Ceiling fan
- City view
- Cleaning before checkout
- Coffee
- Coffee/tea maker
- Conditioner
- Contactless Check-In/Out
- Cooking basics
- Deadbolt lock
- Dining area
- Dining room
- Dining table
- Dishes & utensils for children
- Dishwasher
- Dryer
- Emergency exit
- Essentials
- Family
- Fenced yard
- Fire Extinguisher
- Fireplace
- First aid kit
- Free parking
- Free WiFi
- Freezer
- Game room
- Games
- Garage
- Golf
- Hair Dryer
- Hangers
- Heating
- High chair
- Hospital nearby
- Hot water
- Ice maker
- Internet
- Kitchen
- Kitchen utensils
- Lake
- Lake front
- Lake view
- Linens
- Luggage dropoff allowed
- Massage
- Meal delivery
- Medical emergency contact
- Microwave
- Outdoor dining
- Outdoor firepit
- Outdoor furniture
- Outdoor grill
- Outdoor lighting
- Oven
- Pack n play travel crib
- Police emergency contact
- Private chef
- Private chef on request
- Private entrance
- Private parking
- Rain Shower
- Refrigerator
- Shampoo
- Shower
- Shower gel
- Smart TV
- Smoke detector
- Stove
- Suitable for children
- Suitable for infants
- Toaster
- Toilet
- Towels
- Tub
- TV
- Washing Machine
- Water view
- Waterfront
- WiFi speed (250+ Mbps)
- Wine glasses
- Wireless
Terms & rules
- Smoking allowed: No
- Pets allowed: No
- Party allowed: No
- Children allowed: Yes
Availability
November 2026
- Sun
- Mon
- Tue
- Wed
- Thu
- Fri
- Sat
- 1 $600
- 2 $600
- 3 $600
- 4 $600
- 5 $600
- 6 $600
- 7
- 8 $400
- 9 $400
- 10 $400
- 11 $400
- 12 $400
- 13 $496
- 14 $546
- 15 $400
- 16 $400
- 17 $400
- 18 $400
- 19 $400
- 20 $444
- 21 $473
- 22 $400
- 23 $400
- 24 $400
- 25 $777
- 26 $824
- 27 $820
- 28 $614
- 29 $400
- 30 $400
December 2026
- Sun
- Mon
- Tue
- Wed
- Thu
- Fri
- Sat
- 1 $400
- 2 $400
- 3 $502
- 4 $528
- 5 $526
- 6 $400
- 7 $400
- 8 $400
- 9 $400
- 10 $400
- 11 $488
- 12 $472
- 13 $440
- 14 $400
- 15 $400
- 16 $400
- 17 $423
- 18 $534
- 19 $545
- 20 $463
- 21 $410
- 22 $431
- 23 $518
- 24 $748
- 25 $835
- 26 $809
- 27 $693
- 28 $591
- 29 $529
- 30 $680
- 31 $651
- Available
- Pending
- Booked
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