Family-friendly holiday rentals in Oshkosh

Woodside Cottage Guest House-Close to Road America

Woodside Cottage in the Kettle Moraine forest of East Central Wisconsin offers a quiet private getaway for Road American race fans, golfers or those wanting just to have a break from the city and explore the area. This 2 bedroom guesthouse can host 8, with laundry, full kitchen, living room and outdoor fire pit. Due to family guest allergies, we are pet free. Located 4 miles from gate 4 at Road America and 20 miles from Whistling Straits golf course. WIFI available, but unreliable. 3 cars MAX

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.

Entire Suite-Short drive to Lambeau, Zoo, Downtown

Private side entrance at ground level featuring large windows with natural light, private bathroom with toiletries, laundry room with washer/dryer, private family room with couch, TV with Hulu, wireless, microwave, coffee maker, bottled water, and a mini fridge. You have the entire floor to yourself, as we live upstairs. House is located in a quiet country subdivision. Deer, birds and other wildlife are daily visitors. Easy drive to Lambeau Field, the airport, and downtown Green Bay!

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.

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.

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.

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.

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.*

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!