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Captain`s Quarters | Lake Michigan views for 14

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A residential area with a house featuring a garage, a lawn, and a view of the ocean.
A modern living room with a large TV, comfortable seating, and a view of the beach.
An outdoor seating area with a fire pit, a swing, and a sofa facing a body of water.
A modern bedroom with a large bed, a view of the sea, and a window with curtains.
A modern bathroom with a large bathtub, a fireplace, and a view of the outdoors.

Reviews

10 out of 10
Exceptional

Highlights

  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Discover nearby landmarks
    Walk to Lake Michigan
5 bedrooms3+ bathroomsSleeps 14

Popular amenities

  • Barbecue grill
  • Arcade/game room
  • Air-conditioning
  • Refrigerator
  • Washing machine
  • Garage parking available

Explore the area

View in a map
Sheboygan, WI
  • Place, Lake Michigan
    ‪1 min walk‬
  • Place, St. Peter Claver Parish
    ‪3 min drive‬
  • Place, Blue Harbor Resort & Conference Center Water Park
    ‪5 min drive‬

Rooms & beds

5 bedrooms (sleeps 14)

Bedroom 1

1 King Bed and 1 Single Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 King Bed and 1 Single Bed

Bedroom 5

2 Double Beds and 2 Single Beds

3 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Spaces

Kitchen
Separate dining area
Dining area

About this property

Captain`s Quarters | Lake Michigan views for 14

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.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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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 # 5426891vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that 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 and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Sheboygan

Located in Sheboygan, this holiday home is on the waterfront. John Michael Kohler Arts Center and James Tellen Woodland Sculpture Garden 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. Travelling with kids? Consider Above & Beyond Children's Museum and Bookworm Gardens. Take the opportunity to explore the area for water adventures such as power boating and other activities like birdwatching.
Map
Sheboygan, WI

What's nearby

  • Lake Michigan - 1 min walk - 0.1 km
  • St. Peter Claver Parish - 3 min drive - 1.8 km
  • Blue Harbor Resort & Conference Center Water Park - 5 min drive - 2.9 km
  • John Michael Kohler Arts Center - 6 min drive - 3.2 km
  • Whistling Straits Golf Course - 21 min drive - 31.2 km

Getting around

  • Milwaukee, WI (MKE-General Mitchell Intl.) - 71 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Nine O Two - ‬3 min drive
  • ‪House Divided - ‬9 min walk
  • ‪Limelight Pub - ‬3 min drive
  • ‪Mi Fortuna Mexican Restaurant - ‬17 min walk

Frequently asked questions

Is Captain`s Quarters | Lake Michigan views for 14 pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Captain`s Quarters | Lake Michigan views for 14?

As of 15 Oct, 2026, prices found for a 1-night stay for 2 adults at Captain`s Quarters | Lake Michigan views for 14 on 26 Oct, 2026 start from S$2,151, 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 at Captain`s Quarters | Lake Michigan views for 14?

On-site parking is available at the property.

What time is check-in at Captain`s Quarters | Lake Michigan views for 14?

Check-in begins at 4:00 PM.

What time is check-out at Captain`s Quarters | Lake Michigan views for 14?

Checkout is at 10:00 AM.

Where is Captain`s Quarters | Lake Michigan views for 14 located?

This family-friendly Sheboygan holiday home is located on the waterfront, within 1 mi (2 km) of St. Peter Claver Parish and Lake Michigan. Blue Harbor Resort & Conference Center Water Park and Sheboygan South Pier are also within 2 miles (3 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
In a word: Incredible!! I have rented over 50 VRBOs over the years in multiple countries. Captain 's quarters may be the finest ever. Communication from the host was outstanding. Instructions easy to follow and thorough. The home is significantly better than pictures show. Brand new and no detail not thought out. Bedding as if staying at the Ritz. And the views both moon and sun rising, breathtaking. See pics. Thank you for making our annual brother's motorcycle trip one to remember.
Stayed 2 nights in Sep 2026

About the host

Hosted by Tyler Le Roy

Host profile image

Languages:

English
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