Holiday rentals with breakfast in Sheboygan County

Find and book unique rentals with breakfast on Airbnb

Top-rated rentals with breakfast in Sheboygan County

Guests agree: these breakfast rentals are highly rated for location, cleanliness and more.

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Top guest favourite

A bright living area showcases a spacious dining table with place settings, and a cozy red armchair positioned nearby. Large sliding doors reveal an inviting patio space, while a television stands against the wall opposite, enhancing the relaxing atmosphere.

Home in Sheboygan

4.98 out of 5 average rating, 103 reviews

Relaxing Sheboygan/Kohler Getaway

Newly remodeled townhouse with all the comforts to make you feel at home in quiet neighborhood, boasting a spacious backyard w/patio, fire pit & free parking. Amenities include well-equipped kitchen, 2 BR & 2 BA, washer/dryer, wi-fi, & smart TV. Conveniently located within minutes to Village of Kohler, Downtown Sheboygan & Lakefront, Black Wolf Run, Whistling Straits (14 min), Road America (18 min), Kohler-Andrae State Park (16 min), grocery stores, restaurants, shopping & local entertainment.

Top guest favourite

The exterior of a spacious two-story house is shown, featuring a combination of stone and siding. Large windows and a welcoming porch are surrounded by lush greenery, including mature trees and ornamental plants, creating a serene outdoor environment.

Home in Plymouth

5 out of 5 average rating, 16 reviews

Large House near Road America. Breakfast Included!

Wirewalker Family Farm is a private Bed and Breakfast nestled in the heart of Sheboygan Co. Enjoy private access to the entire 6 bed/3 bath house. Fully equipped chef's kitchen, comfortable furnishings, high end linens. Space for all to spread out in the large kitchen, family rm, sitting rm and sun rm. Dining rm seating can be expanded to seat 25. Experience the thrill of Road America, championship golf at Kohler or world class fishing, hunting and driving in the Kettle Moraine State Park.

A spacious, two-story house with a light-colored exterior is surrounded by a well-maintained green lawn. A covered porch is visible, along with several trees and hedges providing greenery. The property includes an adjacent structure that is likely a garage.

Guest suite in Howards Grove

J & L Country Oasis

Enjoy your stay in Howards Grove at J & L Country Oasis. We provide convenient off street parking. We are located 10 minutes from Whistling Straits Golf Course and Elkhart Lake Home of Road America, The Village of Kohler, American Club, Black Wolf Run Gulfing. close to Lake Michigan, Milwaukee and Green Bay. Are you interested in hiking or biking Kettle Moraine State Forest is only about 30 minutes from us. Have any more questions, just ask thru Airbnb or text me at Larry WAO-AJG-GMJG

Top guest favourite

A spacious living area features a dark leather sectional sofa with colorful throw pillows. A textured ottoman sits in front, while natural light streams through large windows, illuminating the warm brick wall and wooden furniture. A decorative coffee table holds books and a candle.

Loft in Sheboygan

4.97 out of 5 average rating, 111 reviews

Spacious/stylish, 2br loft

Lots of space in active downtown Sheboygan. Full kitchen w/essentials, washer/dryer, 1.5 baths, 2 queen, 2 twin ready for family/friends. Stocked w/home essentials. 3 Smart TVs, free WIFI. Pay-as-you-go parking lot in rear but free nights/weekends. Wonderful walkable neighborhood near shops, restaurants, art & children’s museum, river walk & lake front (a bit further). Short drive to Kohler, Whistling Straits golf course, Shops at Woodlake & Kohler Design Center. Marcus cinema near by.

A cozy room features an original brick wall, a queen-size sleep number bed, and a small dining area with a wooden table and chairs. A double whirlpool tub is positioned nearby, with a private bathroom visible. A flat-screen TV is mounted on the wall.

Flat in Sheboygan

4.84 out of 5 average rating, 31 reviews

Helene's room

Our 4-room B&B is the perfect couple's retreat, located on a working aquaponics farm on the shores of Lake Michigan. Fresh farm breakfasts are included daily. Enjoy our complimentary 9 hole golf course and foot golf course. Free wi-fi and satellite TV. Common area game room includes pool table, bar area, and satellite TV. Family friendly cottage is ideal for family reunions & parties. Event barn is available for weddings & other events from May - October. Call us for more information

Guest favourite

Private room in Sheboygan

4.98 out of 5 average rating, 45 reviews

Doris's room

Guest favourite

Private room in Sheboygan

5 out of 5 average rating, 15 reviews

Ella's room

Top guest favourite

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.

Flat in Sheboygan

4.98 out of 5 average rating, 179 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.

Top guest favourite

A serene sunset scene is displayed over the lake and river, with oranges and blues blending in the sky. Silhouetted trees and buildings frame the view, while the calm waters reflect the twilight colors. Streetlights line the road, illuminating the peaceful surroundings.

Guest suite in Sheboygan

5 out of 5 average rating, 54 reviews

Unmatched Location, Views, & Style. Welcome Home!

Be in the heart of the all the action, The lake, river, marina, boardwalk, and downtown are mere steps from this newly constructed gem. The blue house on the hill is perched where the mouth of the Sheboygan River meets Lake Michigan. Take in the view mornings, evenings, and in between from the stunning kitchen, living room or sailboat shaped front porch. Entertain openly and relax at this one of a kind property. No stairs required. Ramp for easy age friendly access.

The exterior of a two-story house is displayed, showcasing a combination of gray siding and a brown roof. A landscaped yard features pink rose bushes and decorative rocks, complemented by tall grasses, creating a welcoming atmosphere.

Home in Sheboygan Falls

4.93 out of 5 average rating, 14 reviews

River Meadow Getaway in Sheboygan Falls

Welcome! Whether for work, pleasure, or something in between, please come and enjoy our country setting with city convenience. Relax at a campfire and take in the view. Walk or bike downtown for shopping and dining. Feeling adventurous? Explore the Sheboygan River meadow beyond our back yard, or kayak the gentle rapids. Excellent golf, spas, arts, and racing are within 15 minutes. Both at home and around town, we think you'll love your stay. —Ed and Amanda

Guest favourite

The historic building features a classic white facade with green shutters and flower boxes beneath the windows. A private staircase is visible on one side, leading to the upper level. Soft lighting highlights the welcoming entrance and the surrounding floral landscaping.

Hotel room in Sheboygan Falls

4.95 out of 5 average rating, 42 reviews

The Rochester Inn - Signature Two-Story Suite

Welcome to The Rochester Inn, a historic hotel built in 1848, located in downtown Sheboygan Falls, WI. Our elegant & charming two-story suites are located upstairs. The first-floor sitting room is appointed with fine wood furnishings, flat-screen TV & a wet bar. Climb your private staircase leading to the bedroom with a queen-sized four-poster bed & attached bathroom, including two-person whirlpool or deep-soaking tub...truly a luxurious experience!

Guest favourite

A historic log home is set on a grassy area, featuring a sloped roof and a vibrant red entrance. Two large windows complement the facade, while flower pots add a touch of greenery. The porch area invites relaxation with seating options.

Guest suite in Plymouth

4.9 out of 5 average rating, 51 reviews

Settlement Suite

Stay in a spacious suite in the entire lower level of a restored historic log home originally built by immigrants. The home is located on a hill on a 7 acre property. The suite has its own private entrance. Your stay includes a full continental breakfast. Looking for privacy, peace and beauty? This is your place. Located close to Road America, Kohler, Elkhart Lake, historic Plymouth, great golf, and 5 minutes to the Kettle Moraine hiking trails.