Holiday rentals with a fire pit in Sheboygan

4.97 out of 5 average rating, 321 reviews

The cottage is surrounded by trees, featuring a well-maintained exterior with a shingled roof and a welcoming front path. Colorful flowers and greenery adorn the entrance, while large windows allow for ample natural light. A cozy sitting area is visible near the front door.

Cottage in Oostburg

Sandalwood Cottage - 300 Feet From Lake Michigan

A HIDEAWAY one mile East of I-43 nestled in beautiful wooded acreage across from Lake Michigan, on a private drive. Just South of Sheboygan. Close by: Whistling Straits & PGA golf courses. Ice Age Trail in the Kettle Moraine, Elkhart Lake - Road America, Charter Fishing, Kohler Andrae State Park, Several State & local beaches, & several 5 star restaurants. 2 hours & 20 min from Chicago. 45 min from Milwaukee, 65 min from Green Bay. Rest, Relax and Unwind in the tranquil setting at Sandalwood.

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.

4.97 out of 5 average rating, 111 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.

4.97 out of 5 average rating, 186 reviews

Couple's or Family fun- With outdoor Hot Tub!

Enjoy a Day or week for couples or families at this Beautifully updated beach house just one block from the Lake. Enjoy the backyard with pergola & 2-6 person Hot Tub ALL WINTER! Watch the sunrise & sunset from the second floor master balcony. Walk to the lake & beech just across the street. Close to downtown and parks. This three bedroom home will impress. Tastefully decorated seasonally. Large bathroom w/deep soaking tub. For treasure hunters, a Metal detector for family fun at the beach.

The kitchen area offers light wood cabinetry and a breakfast bar, with a dining table that seats four. Large sliding glass doors provide views of the lake, while ample counter space accompanies a full-size refrigerator and modern appliances.

4.86 out of 5 average rating, 218 reviews

Dog Friendly Cozy Cottage Rental on Lake Michigan!

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4.72 out of 5 average rating, 139 reviews

An aerial view captures the layout of the property, showcasing a cluster of buildings surrounded by lush greenery and a small pond. Farm fields extend in all directions, while trees add a touch of vibrant color to the landscape.

Barn in Sheboygan Falls

Quiet Country Charm

Cozy barn loft with rustic charm. This newly renovated private loft sleeps 4 with the possibility of 1 or 2 more if you don’t mind sleeping on an air mattress. This room includes a bathroom with shower and small efficiency kitchen with microwave, coffee maker, and small refrigerator. The futon pulls out to a double bed. This relaxing local comes complete with barnyard animals for an authentic Wisconsin experience! You won’t forget the peaceful surroundings of this rustic destination.

4.94 out of 5 average rating, 162 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, 189 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.

The exterior of a charming house is depicted, showcasing a welcoming front porch with steps leading up. The porch features a small seating area and decorative plants, while lush green grass frames the path, adding to the inviting ambiance.

4.97 out of 5 average rating, 215 reviews

Logan's Guest Nest

Logan's Guest Nest is located in a nice small town feel area. With a small look on the outside your Nest has a big feel on the inside. Spacious rooms and quiet area to rest after a day at the many beaches lining Lake Michigan. Or coming back from the races at Road America. Not to mention a day of golf at the many area courses, Whistling Straits maybe. All these wonderful outings are just minutes from the Nest. Plenty of local dinning or delivery for a nice ending of the day.

5 out of 5 average rating, 227 reviews

Cabin in Cascade

hot tub and sauna on 5 private acres

Looking for a cozy winter retreat? Experience the Bird House, a tranquil Scandinavian-inspired private woodland paradise. Melt away stress in the hot tub and infrared sauna as you take in peaceful views of the meadow. Explore snowshoe and cross-country ski trails nearby in the scenic Kettle Moraine. Stream your favorite movie on the projector near the fireplace or unwind at SoLu winery, just a minute down the road. Near Road America, Kettle Moraine State Forest, and Dundee.

A welcoming living area is highlighted by a warm orange couch with blue accent pillows. A modern lamp with a red base stands beside it on a side table. A framed painting adds character, while a plant is visible through a doorway leading to another room.

4.94 out of 5 average rating, 144 reviews

King Bed Near Lake w/ Fire Pit & Pack N Play

Welcome to the Getaway! Getaway: noun - an act or instance of getting away; a place suitable for a vacation You will unwind in this peaceful 3 bedroom lower unit near Lake Michigan, Whistling Straits and Kohler/Andrae State Park. You can enjoy an evening around the fire pit, or if you don’t feel like staying in, head out to discover some of Sheboygan’s many hidden gems. If this unit is booked for your dates, send me a message to ask about our other available listings.

The image captures a scenic view from the deck, showcasing a lush green backyard leading to the shoreline of Lake Michigan. A fire pit is visible on the grass, and white planters frame the deck, while the sky displays a soft gray hue.

4.94 out of 5 average rating, 210 reviews

Walk-Out Lake Michigan Beach • Fire Pit • Sleeps 8

One of the few homes in Sheboygan that walks out onto the sands of Lake Michigan, this 3 bedroom/ 2 bath home is meant for total relaxation and fun. The open kitchen, dining and living room is full of light from the sliding glass doors on the back of the house, which access a deck and a large back yard. Upstairs is a spacious loft with a pull out couch. Fire pit in the back yard. Just steps from a playground at King Park. Amazing sunrises, worth waking up for.

4.95 out of 5 average rating, 144 reviews

*Front porch, fenced in backyard- PetsWelcome*

Peaceful bohemian retreat with a lively vibe! Perfect for couples, remote workers, girls weekends, golf outings and families! A short walk /bike ride downtown, to the lake or farmer's market. Visit locally owned shops and the world-renowned Kohler Art Museum. Only a 10 minute drive to the famous Whistling Straits/Irish golf course or Kohler Water Spa. Whatever brings you here, we look forward to your visit. Come and enjoy everything Sheboygan has to offer!

Popular amenities for Sheboygan Holiday Accommodation with Fire Pit

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Holiday House Rentals with a fire pit

The Victorian home showcases a charming, multi-level façade with intricate details and a light-colored exterior. Welcoming porches are present at the front, surrounded by well-maintained landscaping featuring green grass and vibrant flowers, all under a clear blue sky.

5 out of 5 average rating, 82 reviews

Updated Victorian in the Heart of Sheboygan

The main living area features a mix of seating options, including a modular sectional sofa and lounge chairs. A decorative area rug sits under a circular coffee table, while large windows offer views of the surrounding greenery. A fireplace enhances the inviting ambiance.

5 out of 5 average rating, 32 reviews

Norwind Ranch - Peaceful Retreat Near Road America

4.89 out of 5 average rating, 104 reviews

The exterior of Shalom House showcases a Frank Lloyd Wright style design, featuring a harmonious blend of stone and wood materials. Large windows allow for ample natural light, and a welcoming entryway is highlighted by decorative stonework.

Home in West Bend

Entire Use of Shalom House

4.79 out of 5 average rating, 14 reviews

Home in Ellis Historic

Walk to the Beach, Walk to Town

A serene beach stretches along the shoreline, with gentle waves lapping at the sandy coast. The sky is painted with soft pastel hues as the sun sets, casting a warm glow over the water. A few trees line the beach in the distance.

5 out of 5 average rating, 15 reviews

Clara Vida Inn- 1/2 Block from Lake and beach!

A well-lit game room features an air hockey table with blue LED lighting, a green pool table, and a bar area with seating for four. A washer and dryer unit is positioned against the wall, while a television is mounted for entertainment.

4.96 out of 5 average rating, 26 reviews

Relax & Play- Walking distance to food & drinks

5 out of 5 average rating, 26 reviews

A two-story cottage is depicted, featuring a spacious deck and an outdoor grilling area. Surrounding greenery offers shade, while a clear view of the driveway is visible. Stairs lead toward the entrance. The structure showcases a combination of light-colored siding and contrasting railings.

Home in Oostburg

Due to cancellation 4th of July Available!

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.

4.91 out of 5 average rating, 53 reviews

Sheboygan Riverside Condo

Apartment rentals with a fire pit

The exterior of a two-story residence is visible, featuring a well-kept front yard with a variety of flowering plants and shrubs. A concrete pathway leads to a set of stairs, which ascend to the entrance. Tall trees provide shade, enhancing the greenery surrounding the home.

4.92 out of 5 average rating, 12 reviews

Logan Ave Holiday House - Upper

Apartment in Elkhart Lake

The exterior of a renovated farmhouse is displayed, showcasing light grey siding and a wooden deck adorned with potted plants. Ample greenery surrounds the property, and multiple windows reflect the surrounding natural light. A cozy seating area is visible on the deck, inviting relaxation.

5 out of 5 average rating, 63 reviews

Lime Ridge Guest House

4.89 out of 5 average rating, 9 reviews

Storybook Home - 1 mi to Lake & Downtown Sheboygan

A living room is presented with a flat-screen TV mounted on a white unit. A gray sofa and a blue accent chair offer comfortable seating, while a coffee table with decorative items occupies the center. Natural light enters through a nearby window.

4.63 out of 5 average rating, 19 reviews

Sheboygan Getaway with Yard: 1 Mile to Lake Michigan

The modern kitchen features sleek gray cabinetry and a spacious countertop. Essential appliances include a range, microwave hood, and refrigerator. A television is mounted on the wall for entertainment, and light is provided by recessed lighting in the ceiling.

4.5 out of 5 average rating, 22 reviews

Cozy and Modern Upper Near Lake

Apartment in Campbellsport

A dining area is showcased, featuring a wooden table set with two plates. A vase with flowers sits at the center. Large windows frame the view of verdant trees, allowing natural light to fill the space.

4.97 out of 5 average rating, 105 reviews

GGG Spacious Log Cabin apartment on the IAT

A tranquil bedroom is presented with a light-toned wooden bed adorned with soft bedding. Nightstands with lamps are positioned on either side, while large windows allow natural light to fill the space. A nature-themed artwork adds a visual focal point above the bed.

4.96 out of 5 average rating, 28 reviews

Lovely modern home with fire pit

The living area features two light-colored sofas arranged around a wooden coffee table. A TV is positioned on a nearby stand, while a patio door allows natural light to enter. A small round table with chairs is also visible against the wall.

Apartment in Plymouth

4.67 out of 5 average rating, 3 reviews

Centrally located apartment.

Cabin rentals with a fire pit

4.94 out of 5 average rating, 106 reviews

A charming log cabin features rustic wooden architecture, complemented by red window frames. Surrounded by lush greenery, the structure offers a welcoming front porch. Natural light bathes the exterior, enhancing the serene setting among the trees, with a pathway leading to the entrance.

Cabin in Campbellsport

Wooded CABIN-Sunset & Lake Views/Kayak to Tiki Bar

4.98 out of 5 average rating, 54 reviews

A spacious living area features a stone fireplace surrounded by wood paneling and large windows allowing natural light. Cozy seating is arranged around a coffee table, with a television mounted above the fireplace. The décor includes welcoming signs and artwork, enhancing the rustic charm of the space.

Cabin in Valders

Cozy cabin in the woods

5 out of 5 average rating, 57 reviews

The exterior of the rustic cabin is framed by lush greenery, showcasing a combination of log and stone construction. A circular stone patio features a wooden bench and a fire pit, inviting gatherings in a tranquil outdoor setting surrounded by nature.

Cabin in Cascade

Rustic Chic Cabin in Kettle Moraine

5 out of 5 average rating, 24 reviews

An aerial view showcases the cabin nestled among lush greenery, adjacent to a serene lake. A well-maintained path leads from the home to the water's edge, framed by trees reflecting vibrant autumn colors. The peaceful landscape invites relaxation and exploration.

Cabin in Cascade

Lakeside Cabin Retreat Private Lakehouse Hideaway!

5 out of 5 average rating, 24 reviews

A deck furnished with wooden chairs offers a view of the reflective lake surrounded by vibrant autumn foliage. Colorful trees frame the water, enhancing the natural setting. Tables and seating are visible in the open space below, providing areas for gathering.

Cabin in Plymouth

Walking distance to Road America, Lakefront

5 out of 5 average rating, 30 reviews

The farmhouse is set against a colorful sunset, showcasing a blend of traditional and modern architecture. A spacious green yard surrounds the home, with a picnic table visible on the patio. Lush trees and open space contribute to the serene country atmosphere.

Cabin in Newton

Modern Country Retreat

4.78 out of 5 average rating, 27 reviews

The interior living area features exposed wooden beams and large windows that allow natural light to illuminate the space. Comfortable seating arrangements include sofas and armchairs beside a wood-burning stove. A dining area with a large table is visible in the background, enhancing the open atmosphere.

Cabin in Campbellsport

Peaceful Lakeview Cabin Stay On Private Peninsula