Family-friendly vacation rentals in Oshkosh

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Top-rated family-friendly rentals in Oshkosh

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

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Guest favorite

Farm stay in Montello

4.88 out of 5 average rating, 339 reviews

Escape to Evergreen Homestead 20 Acres of Nature

Discover the perfect getaway at our charming, fully furnished private apartment, set on a peaceful 20-acre homestead. Start your day with fresh farm eggs and explore the beauty of a lush pine forest right on the property. Relax on the porch, soaking in the tranquil atmosphere, or enjoy some fun with retro arcade games. Our dog-friendly retreat also offers the chance to interact with friendly goats. Experience the serenity and warmth of country living at its best—just a short drive from the Dells

Guest favorite

Farm stay in New London

4.97 out of 5 average rating, 181 reviews

Irish Acres Farm"Glamping" FAIRY CABIN tiny home

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

Cottage in Fond du Lac

4.97 out of 5 average rating, 251 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. 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 bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Guest favorite

Home in Scandinavia

4.95 out of 5 average rating, 164 reviews

Peterson Mill Schoolhouse

The Peterson Mill Schoolhouse is a rural and historic one classroom school converted into a guest house. Located next to a trout stream and operating dairy farm, you can sit on the open-air porch, relax by the creek, or take a walk on the country roads. The Schoolhouse is open year-around, welcoming all who enjoy fishing, biking, hunting, and other outdoor activities. Enjoy your time in the peaceful surroundings or drive 15 minutes to the beautiful Waupaca Chain-O-Lakes.

Guest favorite

Guesthouse in Oshkosh

4.95 out of 5 average rating, 187 reviews

Cottage on Lake Winnebago

Furnished Cottage on Lake Winnebago with beautiful sunrises. 1 bedroom with queen bed. There is plenty of space for air mattresses in common areas. 1 queen air mattress available. One bath, full kitchen fully stocked with dining area, bring your own food to prepare. Bring your water toys or boat, launch nearby and dock access in warmer months with great fishing. Winter months, bring your snowmobile, trails nearby. Great ice fishing when lake is frozen and ice is safe.

Guest favorite

Home in Sheboygan

4.94 out of 5 average rating, 190 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.

Guest favorite

Cottage in Manitowoc

4.88 out of 5 average rating, 128 reviews

Year Round Home on English Lake in Manitowoc Cty

Lovely year round home on English Lake in Manitowoc county. Non motorized boats are available during the summer. 25 miles from Kohler resort. 45 minutes away from Green Bay Packers and 75 miles north of Milwaukee. For winter arrival, you do need to have an all wheel or 4 wheel drive. There are two hills that can be tricky without these! If you are looking for a date that is blocked out, please inquire as we may be able to open up more dates.

Guest favorite

Guest suite in Appleton

4.95 out of 5 average rating, 119 reviews

Cozy Guest Unit with 2 Bedrooms

No cleaning fee/Appleton Licensed Tourist Rooming House! This is your home away from home for EAA, Lawrence U, the Packers, business, PAC, Scheels USA Fields & more. The spacious, lower half of our split-level home with 2 bedrooms (queen & double/single)has its own private keyed entrance, bath & basement living room. Add’l amenities include office chair/desk, fridge, microwave, washer/dryer & Keurig coffee machine. *No kitchen.*

Guest favorite

Rental unit in Waldo

4.98 out of 5 average rating, 270 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Guest favorite

Cottage in Fox Lake

4.85 out of 5 average rating, 308 reviews

The Little White Cabin, Fox Lake WI

This 2 bedroom rustic cottage feels like you're home at the beach. Light colors, easy comfort. Everything you would expect for a summer cottage, boat launch is close, great fishing, water skiing, jet skiing. Winters are for ice fishing and snow mobiles. Cozy comfort. If you are a hunter, this is your cabin for longer term rentals during fall/winter. LGBTQ friendly!

Guest favorite

Rental unit in Port Washington

4.93 out of 5 average rating, 281 reviews

Homeport

The apartment is a remodeled former "Summer Kitchen" in the lower level of our cream city brick home. We are located in the heart of downtown next to the marina, close to parks, steps away from restaurants, coffee shops & bars. Lake Michigan is just outside the door! We invite couples, solo adventurers, and business travelers for short and long-term stays.