Properties

16 properties  

$299-1,949/night

Pine Dunes Cabin

4 Bedrooms • 3 Baths • Sleeps 7-10
Internet Wood Stove Beach Hot Tub
🏖 600 ft to Lake Michigan beach
🔥 3 decks + fire pit
🛁 6-person Softub Hot tub (Nov–Apr)
📶 High-speed Starlink WiFi
🍳 Fully stocked chef’s kitchen
🛌 Sleeps up to 10 guests
🎮 Loft hangout zone + smart TVs
⛳️ Near world-class golf, trails, Road America & more

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$259-1,169/night

The Sandwood Cottage

4 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 7-10
Internet Firewood Provided Beach
🏖 500 ft to Lake Michigan beach
🕹 Full basement arcade + ping-pong
🛋 Professionally designed interiors
📶 High-speed Starlink WiFi
🍽 Chef’s kitchen + coffee bar
🔥 Wood fire pit & patio
🛌 Sleeps 10 comfortably
⛳️ Close to world-class golf, dunes & Road America

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$399-3,559/night

The Big Montana at Elkhart Lodge

7 Bedrooms • 3 Baths • Sleeps 11-18
Allows pets Internet Fireplace
🏕️ Massive Log Cabin on 5 Private Acres
🛌 Sleeps 18 | 7 Bedrooms | 3 Bathrooms
👨‍🍳 Fully Loaded Kitchen + Group Dining Area
📺 Cozy Living Room with Large Smart TV
🌲 Spacious Deck with Grill & Nature Views
🏁 1 Mile to Road America Raceway
🏖️ 2 Miles to Elkhart Lake Beach at Fireman’s Park
🔥 Perfect for Reunions, Race Weekends & Retreats
🐾 Pet-Friendly Cabin ($55/night per dog, with notice)

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$984-5,389/night

The House at Wilson Shore

6 Bedrooms • 4 Baths (3 full, 1 half) • Sleeps 11-15
Internet Fireplace Beachfront
🏖️ Private Sandy Beach on Lake Michigan
🔥 Waterfront Fire Pit for Cozy Evenings
🧖‍♀️ New Lakeview Sauna
🪟 Open-Concept Living with Wall-to-Wall Lake Views
🛏️ 6 Bedrooms – Sleeps Large Groups Comfortably
🍳 Fully Equipped Kitchen & Spacious Dining Area
☀️ Expansive Deck for Coffee, Sun & Scenic Relaxation
🌲 Wooded, Tranquil Neighborhood Near Kohler-Andrae State Park
🚗 Minutes to Sheboygan, Kohler, & Road America
🔐 Private Home with Seamless Self Check-In

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$399-1,199/night

Old Trees Farm

5 Bedrooms • 3 Baths • Sleeps 1-12
Internet Fireplace
🧱 100+ Year Old Cream City Brick Farmhouse
🍳 Chef’s Dream Kitchen with 2 Fridges, 2 Dishwashers & Wet Bar
🛏️ 5 Bedrooms, 3 Full Bathrooms – Perfect for Families & Retreats
🔥 Cozy Living Room with Gas Fireplace & Large Smart TV
🎶 Premium Sonos Sound System Indoors & Outdoors
🐐 Meet Friendly Farm Animals + Enjoy Fresh Eggs Daily
🔥 Private Outdoor Fire Pit & Covered Porch
🐾 RV Hookup Onsite + Year-Round Access
🌄 Close to Road America, Kettle Moraine, Elkhart Lake & More

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$119-459/night

Waves of Happiness Lower Condo

2 Bedrooms • 1 Bath • Sleeps 2-4
Internet Fireplace Beach View
🛏️ 2 Comfy Bedrooms (King + Queen)
🌊 Dual Decks w/ Stunning Lake Views
👣 Walk to Beach, Boardwalk & Restaurants
🔥 Electric Fireplace for Cozy Nights
📺 Roku Smart TV & High-Speed WiFi
🧼 In-Unit Laundry + Full Kitchen
🪂 Steps from Kite & Parasailing-Friendly Park
🚗 Free Parking + Walkable to Downtown

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$139-609/night

Waves of Happiness Upper Condo

2 Bedrooms • 1 Bath • Sleeps 4-5
Internet Fireplace Beachfront
🌅 Upper-Level Lake Views from Dual Decks
🏖️ Just 200 Feet to the Beach
🌇 Walkable to Shops, Dining & Riverwalk
🛏️ King + Queen Bedrooms | Sleeps 4
🔥 Electric Fireplace, Roku TV & Cozy Lounge Vibe
☕ Coffee Bar, Full Kitchen & Lake Breezes
🪂 Steps from Kite Park, Surfing & Waterfront Trails
🧺 In-Unit Washer/Dryer + Beach Gear Included

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$219-959/night

Orchard House Retreat

4 Bedrooms • 4 Baths • Sleeps 5-8
Internet Fireplace
🌳 Orchard-Style Backyard w/ Picnic Pavilion & Fire Pit
🚶 Steps to Kohler-Andrae State Park & Black River Trails
🧸Family-Friendly Layout with Kid Play Area
🏡 Charming & Character-Filled Living Spaces
🍽️ Fully Equipped Kitchen for Home-Cooked Meals
🌷 Peaceful Garden Views & Outdoor Oasis
🏖️ Minutes to Lake Michigan Beaches & Sheboygan
🏌️ Close to World-Class Golf (Whistling Straits, Blackwolf Run)
🛍️ Easy Access to Sheboygan Dining & Downtown Shops

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$119-329/night

Uptown Coach House

2 Bedrooms • 1 Bath • Sleeps 1-4
Internet Downtown
🖼️ Globally Curated Art, Furniture & Decor
🛏️ 2 Stylish Bedrooms + 1 Luxurious Kohler Bathroom
🍽️ Modern Kitchen with High-End Appliances
🛋️ Open-Concept Living Space with Smart TV
🏖️ Just 0.5 Miles to North Beach & Lake Michigan
🍷 Walk to Downtown Dining, Shops & Riverfront
📍 Prime Downtown Location – Steps from It All
🚪 Private Entry with Smart Lock

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$239-1,159/night

Rose & Fern's Delightful Seaside Picnic

3 Bedrooms • 3 Baths (2 full, 1 half) • Sleeps 4-8
Internet Fireplace Beachfront
🏖️ 1 Block from Sheboygan’s Best Beach & Lakeshore Walks
🍽️ Chef's Kitchen with High-End Appliances & Tons of Space
🪑 Ultra-Luxe MillerKnoll Seating + Custom Handcrafted Beds
🎨 Local Artisan Artwork & Designer Wood Furniture Throughout
🚲 Free Bikes + Walkable to Downtown, Riverfront & Pier
🛋️ Bright Open Layout
🏡 Charming & Safe Historic Ellis District Neighborhood
🚎 Summer Trolley, Public Bus & Scooters Nearby
📶 Fast WiFi

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$239-2,349/night

Nelly's Place

3 Bedrooms • Sleeps 1-8
Internet Wood Stove Beachfront
🏖️ Private Sandy Beach + Huge Grassy Yard for Games & Fires
🪵 Feels Like the North Woods—But Just 45 Min from Milwaukee
🔥 Multiple Fire Pits + Wood-Burning Fireplace Indoors
🛏️ 3 Bedrooms + Den, 2 Baths, High-End Furnishings & Beds
🧺 2 Washer/Dryers
🚶‍♂️ Walk to Kohler-Andrae State Park & Beachfront Trails
🎯 Yard Games, Basketball, Old-Fashioned Park Play Equipment
🧘 Perfect for All Seasons
🏌️ Near PGA Golf, Kohler Spa, Waterparks & Quaint Towns

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$329-1,479/night

The Pond Cottage

2 Bedrooms • 1 Bath • Sleeps 1-7
Internet Fireplace Beachfront
🏖️ 275 Feet of Private Lake Michigan Shoreline
🍽️ Two Screened Porches + Outdoor Dining Deck with Grill
🛌 Newly Renovated in 2025 – Thoughtful, Cozy, and Stylish
🪵 Set Atop a Scenic Dune on a Quiet, Wooded Lane
🎣 Minutes to Fine Dining, Golf, Kohler Spa, Arts, & Charter Fishing
🚶‍♀️ Peaceful Walks, Wildlife Sounds & Total Tranquility
🌲 Ideal for Romantic Retreats, Solo Escapes, or Serene Getaways
🔥 Fire Pit, Outdoor Seating & Umbrella for Lounging Lakeside

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