Family-friendly vacation rentals in Lake Winnebago

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Top-rated family-friendly rentals in Lake Winnebago

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming red farmhouse is set against a colorful sky at sunset, surrounded by a picturesque yard filled with wildflowers. The property features a wooden fence and mature trees, contributing to a serene rural atmosphere.

Guesthouse in Richfield

4.94 out of 5 average rating, 254 reviews

Peaceful weekend or extended stay, full amenities

The Country Retreat at the historic Schmitz Family Farm is close to many attractions, ideal for couples, families, girls' weekends, extended stays, business travel, and is dog friendly. Enjoy a sunrise or sunset, get cozy at the fireplace, or indulge in the many activities our area has to offer. We feature two beautiful bedrooms, living room with two sleeper sofas (can also be used as a third bedroom, as door closes for privacy), laundry room, full kitchen, coffee nook, quiet deck and backyard.

Guest favorite

A hot tub is shown in the foreground, its water illuminated in soft light. Behind, a cottage is visible with large windows revealing a warm, inviting glow. The exterior is adorned with twinkling lights that enhance the cozy atmosphere of the setting.

Home in Poynette

4.91 out of 5 average rating, 188 reviews

Island View Hideaway-Peaceful, On Water, Sandbars!

Rent this furnished cottage to enjoy the beauty of nature on the Wisconsin River and Lake Wisconsin. Conveniently located on the Lake Wisconsin waterfront between Madison and the Wisconsin Dells, just 1.5 hours from Milw and 3 hours from Chicago. We are pet friendly for well behaved dogs with a $25/night pet fee per dog. Beautiful views out the large living room windows look onto green, sandbars, islands and the undeveloped distant shores of the Wisconsin River as it opens up into Lake WI.

Guest favorite

A rustic log cabin is surrounded by greenery, featuring a charming wraparound porch with steps leading up to it. The exterior displays wooden beams and a welcoming front, while a small fence encloses the area, creating a cozy, nature-integrated ambiance.

Farm stay in New London

4.96 out of 5 average rating, 182 reviews

Irish Acres Farm Charm Glamping: FAIRY CABIN

Irish Acres Farm is host to guest friendly activities. Sit & relax or join in farm chores, hike, fish, meditate. Light a camp fire and enjoy Nature at her finest. Experience the coziness of a rustic "tiny house" off-grid log FAIRY CABIN set beside a 1 acre spring fed pond. My place is good for couples, solo adventurers, & families (with kids). No pets or therapy animals allowed. We strive to be a tech free zone (NO WIFI or TV's). A true authentic connection with Nature and each other.

Guest favorite

The log cabin features a covered front porch with seating areas, surrounded by landscaped greenery. Tall trees and shrubs frame the property, creating a sense of privacy. A gravel path leads to the entrance, enhancing the rustic charm of the home.

Cabin in Montello

4.95 out of 5 average rating, 128 reviews

True Log Cabin Montello 1/2 hr to WI Dells on 10ac

Lazy Fawn Cabin Escape reality and surround yourself with nature at this quiet peaceful log cabin sitting on 10 acres. Camp fires, grilling or lay in the hammock. 2 bedrooms with queen beds and a large loft with 1 queen and 2 full beds. 1/2 hour from Wisconsin Dells and 7 minutes off I-39. Rustic cabin with all the modern amenities. Area lakes for fishing or recreation, or take a ride to an amazing Amish bakery and shops. 10 minutes to downtown Montello for groceries and restaurants.

Guest favorite

A modern single-story home features a light gray exterior with a striking yellow front door. Large windows provide abundant natural light, while a well-maintained lawn is complemented by colorful flower beds. Skylights on the roof enhance the home's contemporary design.

Home in Cleveland

4.95 out of 5 average rating, 144 reviews

Modern Home Just 40 Minutes from GB NFL Draft

My home is just minutes from Whistling Straits Golf, Road America, Lake Michigan, Parks, Hiking, Biking, Snowshoeing, and Cross Country Skiing. You’ll love my place as it's newly remodeled, modern & cozy. The kitchen and living areas have high ceilings, sky lights & new furniture. The large outdoor living area is perfect for social time. My favorite is the heated bathroom floors. My place is perfect for golfers, wedding groups, couples, business travelers, and families (with kids & dogs).

Top guest favorite

A cozy bedroom features a spacious bed with soft bedding, complemented by a decorative area rug. Natural light filters through a nearby window adorned with sheer curtains, alongside a bedside lamp that enhances the intimate ambiance.

Home in Two Rivers

4.96 out of 5 average rating, 151 reviews

Hammernick Haus | your home away from home.

Spacious 2-story home in a quiet neighborhood near Lake Michigan, Ice Age Trail, etc. (Easy drive to Door County and Green Bay). Enjoy a well-stocked kitchen, modern laundry with steam features, and a cozy front porch for morning coffee. Entertainment includes basketball hoop, CD player with a variety of music from classical to metal as well as board games to enjoy around the table. Perfect for relaxation, working away from home, or adventure. Book your stay today!

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 196 reviews

Beachfront getaway in Sheboygan

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.

Top guest favorite

An outdoor deck features a dining table surrounded by chairs, with a large umbrella providing shade. Beyond the deck, sandy beach and gentle waves of Lake Michigan can be seen, framed by tall grasses, creating a serene coastal atmosphere.

Home in Oostburg

4.96 out of 5 average rating, 187 reviews

Shamba on the Lake, Oostburg, WI

Large guest home , in a rustic setting, on a peaceful 2-acre wooded lot (only 5 homes on a very private road) on Lake Michigan with a large private beach a few feet from the deck. . Magnificent panoramic view, amazing sunrises, serene twilights, magical star-studded night skies. A slice of Paradise you must experience. Located a mile from I43, 40 minutes from downtown Milwaukee, 20 mins. from golf courses in Kohler, 30 mins. from Road America in Elkhart Lake...

Top guest favorite

A relaxing living area features a stone fireplace as its focal point. Comfortable seating options, including a leather chair and a spacious sofa, are arranged around a rustic coffee table. Large windows allow natural light to fill the space, with glimpses of the surrounding scenery.

Cottage in Fond du Lac

4.99 out of 5 average rating, 282 reviews

Beautiful Lake Home.

Our Beautiful two bedroom cottage is located on the shores of Lake Winnebago . Centrally located to many of Wisconsin's best attractions. Less than 1 hour from Milwaukee, Madison, Green Bay, Close to Oshkosh (EAA) and Elkhart Lake. Includes 2 bedrooms, with plush queen beds, 1 full bathroom, Laundry room with washer and dryer. The perfect home for a laid back group of friends, couples or a family to stay with all the comforts of being at home.

Superhost

A sandy beach scene captures a child walking away from a detailed sandcastle, which features tall towers and a round structure on top. The calm waters of Lake Michigan stretch into the background under a clear blue sky.

Home in Two Rivers

4.68 out of 5 average rating, 381 reviews

1 block to Beach- Beach house-Firepit and bikes!

Our cozy little home is the perfect getaway location, JUST ONE block (250 ft) from Lake Michigan; a short 2 minute stroll. Or take our bikes around the town and beach- 2 provided! Our backyard is a perfect hangout area with gas fire pit, patio table & yard games. Kick back & relax! Only 40 minutes to Lambeau Field & Less than an hour to Door County. Book Now Instantly or shoot me a message if you have any questions! Washer and dryer included!

Superhost

The exterior view of a spacious two-story home is shown, featuring a large deck leading to a yard surrounded by lush trees. A propane grill is positioned on the grass, inviting outdoor cooking and gatherings. Two window air conditioning units are visible on the side of the house.

Home in Sturgeon Bay

4.84 out of 5 average rating, 101 reviews

Claybanks | A Woodsy Retreat + 6 acres

This large spacious 4 bedroom, 2.5 bath home is nestled between two beaches and surrounded by 6 acres of beautiful Door County woods in a very quiet corner of our county. Enjoy your time away from the hustle and bustle down by the fire pit, a hike through the woods or take in a nice 1/2 mile stroll down to the waters edge in either direction. A home where memories are made. DCTZ Permit | **3656173117**

Guest favorite

A modern living space features a leather couch with a blue throw blanket draped across the back. A wooden coffee table, displaying magazines and a remote, is flanked by two side tables. The background includes an open kitchen area with contemporary fixtures.

Cottage in Two Rivers

4.99 out of 5 average rating, 273 reviews

~Driftwood Haven Cottage ~

This newly constructed contemporary cottage is both steps from Lake Michigan & Point Beach State Park! Featuring a beautiful open concept living space with wood burning fireplace! This modern minimalistic style cottage is tastefully decorated with local artists work throughout along with many amenities. ***pet fee applies***