Vacation rentals with a patio in Sheboygan County

4.95 out of 5 average rating, 20 reviews

Storybook Home - 1 mi to Lake & Downtown Sheboygan

Welcome to The Fox & Folly Inn 🦊 —a unique whimsical retreat. Perfect for families and those who are kids at heart! 🖼️ Creative and cozy home with art and murals. 🦊🐰🦉Themed with original characters. Audio stories & endless charm! 🛏️ Master Bedroom - King Bed 🛋️ 2nd Bedroom - Bunk Bed = Full Lower, Twin Upper 🛌 Sleeps 5 🛁 1 Full Bathroom - Towels, Hair Dryer+ 🍽️ Fully Stocked Kitchen 🅿️ Off-Street Parking 🏖️Minutes from the beach & Bookworm Gardens 📖Your storybook adventure awaits!

A well-lit bedroom features a spacious bed with a dark headboard and light bedding. Two bedside lamps illuminate the room, complemented by natural light from the two windows. A wall-mounted television adds functionality, while a piece of art decorates one wall, enhancing the inviting ambiance.

4.98 out of 5 average rating, 249 reviews

Modern Upstairs Apt - Steps from Lake Michigan

Have you ever wondered what Lake Life is like? Here is your chance! This is 1 of 2 AirBnB units in this cute duplex Come stay in this beautiful upper apartment located just one block from Lake Michigan. Take a quick walk to the lake in the morning to jump on your fishing boat or take the family to the beach in the afternoon! Located close to shopping and many local bars and restaurants within walking distance. You'll find relaxation and a great time here at the heart of Sheboygan's Shoreline!

Guest favourite

The exterior of the home features a charming two-story design with a gabled roof and a welcoming front entrance. Large windows allow natural light to fill the space. A small seating area is visible on the front patio, complemented by greenery and a neatly landscaped yard.

4.91 out of 5 average rating, 54 reviews

The perfect location!

You will be close to everything when you stay at this 1930s home. Walk three blocks west to Sheboygan's historic downtown to find shops, restaurants, theaters, museums, and a local farmer’s market. Walk two blocks east to the beach, walking/biking trail, marina, and parks. Free street parking, 1-stall attached garage, reliable wifi. All three bedrooms and full bathroom are upstairs. Washer/dryer and 1/2 bath are in the basement. Three window AC units in the summer. Kitchen has basic amenities.

A cozy living area is filled with neutral-toned furniture, including a large sofa, accent chairs, and a circular coffee table. Natural light filters in through large windows, highlighting the wooden floors and a decorative area rug beneath. Soft green accents are present in the lamps and curtains.

4.97 out of 5 average rating, 146 reviews

House Near the Lake

Get out and enjoy nature, then return to a quiet mix of modern and retro in this family home only a block away from Lake Michigan. There are three parks and two beaches within a mile, as well as Terry Andrae State Park about 10 minutes away. If the outdoors aren't your thing, downtown Sheboygan hosts the Kohler Art Center, The Weil Center, Blue Harbor, and the Children's Museum, with Road America only 30 minutes away. Located between Milwaukee and Green Bay, this home has all the conveniences.

A well-appointed bedroom features a spacious bed with white linens and a textured gray throw. Two decorative lamps provide soft lighting on either side of the bed. Bright windows are framed by patterned curtains, and wall art adds a touch of elegance to the neutral-colored walls.

4.96 out of 5 average rating, 54 reviews

Peaceful apartment close to the lake

Beautiful, newly furnished & updated, 2 Queen bedroom upper apartment with large closets, 1 bath, desk with workspace, stocked kitchen, in unit laundry, private balcony, high speed internet, 2 Smart TVs, keyless private entrance Central downtown location walking distance to restaurants/bars, parks, the beach, festivals, Museums, Arts Centers, Stephanie H. Weill Center & more! 10-15 min. driving distance to Kohler golf courses, The Bull at Pinehurst Golf Course, Road America, Elkhart Lake

A newly built farmhouse is set against a clear blue sky, featuring a covered porch that runs the length of the building. Well-maintained grass surrounds the structure, complemented by a gravel pathway and landscaped rocks. A vehicle is parked nearby, adding to the rural ambiance.

5 out of 5 average rating, 41 reviews

Private 3 bd country home 2 miles N of Kohler WI

Summer is coming! 🌞 Book Now! Private newly built house on 25 acres-2 miles North of Kohler. Good Pets stay free, plenty of room to run! Just a short drive to Whistling Straits, Road America and Lake Michigan. A great location to enjoy all Sheboygan County has to offer. Bring the entire family and the dogs. Enjoy your day and return to a spacious home with a newly added putting green and BBQ area. Surrounded by growing fields, many deer, multiple birds and a gorgeous sunset every night.

Guest favourite

4.93 out of 5 average rating, 54 reviews

Sheboygan Chalet | Nature, Arcade, Sauna & Hot Tub

Escape to Sheboygan Chalet—a stunning modern retreat tucked in the woods of the Black River community 🌲 Just two blocks from Lake Michigan and a short walk to Majerle’s Supper Club, this home blends style, comfort, and endless entertainment. Highlights include: 4 spacious bedrooms, sleeps 10+ Chef’s kitchen with quartz island 🍽️ Hot tub, infrared sauna & fire table 🔥 Epic game room with arcades, PS5 & ping pong 🎮 Peaceful wooded views from two decks The perfect year-round getaway!

4.95 out of 5 average rating, 189 reviews

LUX Downtown Escape | Outdoor Movie Screen

Welcome to our beautiful 2-bedroom historic home in Downtown Sheboygan! This charming and well-appointed residence offers a comfortable and stylish stay for your visit to the area. From the Chef’s kitchen, comfortable living room, and peaceful backyard, to its prime location within walking distance of Sheboygan's vibrant nightlife, theater, and restaurants, you'll have everything you need right at your doorstep. The home is also just a few blocks from Lake Michigan's beautiful beaches.

A well-lit living area features a neutral-colored sofa adorned with a soft throw. A glass coffee table sits on a patterned rug, complemented by a wicker basket. Natural light filters through the window, illuminating the space and the nearby armchair.

4.98 out of 5 average rating, 202 reviews

Lovely modern two bedroom home with fire pit

Newly renovated two bedroom home just a mile from the beach and five star restaurants. Enjoy a game of golf at world class Whistling Straight. Car enthusiasts will love Elkhart Lake Road America. Salmon fishing the Great Lake Michigan or just have a relaxing time around the fire pit. There is a laundry with washer/dryer, steamer and folding table. Dogs under 30 pounds. No cats sorry. No smoking in the house. Ample street parking at the front door. Fire pit in back yard.

5 out of 5 average rating, 15 reviews

Sunset Vista- cozy two bedroom retreat

This cozy vacation rental is the perfect place to relax and unwind! Enjoy a warm and inviting fireplace, comfy furnishings, soft lighting, and a fully equipped kitchen ready for your favorite meals. Step outside to a peaceful garden and scenic views — an ideal backdrop for morning coffee or quiet evenings. Whether you’re vacationing with family or friends, this space offers a home-like feel where beautiful memories come naturally. ❌🐾 We currently are not pet friendly.

5 out of 5 average rating, 45 reviews

Clean, Comfy Stay Near Parks, Downtown & Lake!

Enjoy a peaceful stay near Sheboygan’s lakefront, family parks, and downtown eats. This clean, cozy 2BR unit offers everything you need—walkable location, garage parking, full kitchen, and thoughtful touches like old-school Nintendo and local recommendations. ⭐ “Clean, comfy, quiet—close to everything. We’ll definitely stay again!” – Roger ✓ Minutes to downtown & Lake Michigan ✓ Family park across the street ✓ Garage + easy onsite parking

Guest favourite

A serene bedroom is furnished with a spacious bed adorned with decorative pillows. Large glass doors open to a private balcony, while a comfortable armchair and a small tabletop are positioned near the window, allowing natural light to fill the room.