Holiday rentals with a patio in Sheboygan County

4.95 out of 5 average rating, 22 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, 257 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!

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.

4.88 out of 5 average rating, 59 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, 152 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.

4.97 out of 5 average rating, 59 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

4.95 out of 5 average rating, 192 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, 207 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.

4.85 out of 5 average rating, 108 reviews

The exterior of a spacious lakeside home is showcased, featuring large windows and a welcoming porch. A green lawn extends towards the water, accompanied by bright blue kayaks and a swing set. A tall tree provides shade, enhancing the outdoor ambiance.

Cottage in Random Lake

Private 3 bedroom lake house

A beautiful spacious 3 bedroom with sofa bed (sleeps 9 guests) with lake access just steps away from the backyard. Includes washer and dryer, all cooking amenities and a grill, 3 TVs with cable (including Netflix and Disney+ capabilities), a two person canoe n 3 kayaks, hammock, board games, and books for leisure reading. Fish off the private peer. Light the bonfire in the fire pit (firewood included) by the patio onlooking the lake. Pets are allowed with a $200 pet fee.

5 out of 5 average rating, 51 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

5 out of 5 average rating, 13 reviews

An outdoor balcony features a wooden table with colorful place settings and a small planter. Comfortable seating is provided by woven chairs and a red cushioned chair. A decorative privacy screen and clear blue skies create a warm and inviting outdoor space.

Condo in Sheboygan

Welcome to our Cozy Lake Condo!

Welcome to your perfect getaway by Lake Michigan! Cozy 1-bedroom condo with stunning Sheboygan River views! Located across from Blue Harbor Resort, this 2nd-floor retreat sleeps 2 comfortably (4 with pull-out couch). Enjoy 600 sq. ft. of living space plus a large balcony—perfect for morning coffee or evening sunsets. Walk to shops, dining, and the beach. Book your stay and experience Sheboygan from the comfort of your own lakeside haven!

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.

4.92 out of 5 average rating, 71 reviews

Sheboygan Riverside Condo

Experience the Malibu of the Midwest in this stunning 2-bedroom retreat! The king suite offers a private balcony with a cozy fireplace overlooking the serene Sheboygan River. The second bedroom features two queen beds, perfect for families or friends. Enjoy an open-concept living space, modern kitchen, and easy access to Sheboygan's best attractions. With a 2-car garage and nearby conveniences, this is your ideal getaway spot!

A green chair is positioned next to a circular mosaic table, offering a spot to relax. In the background, a wooden railing encloses a patio area with additional seating visible. Lush greenery from surrounding trees adds a natural touch to the inviting outdoor space.