Family-friendly holiday rentals in Oshkosh

Elkhart A-Frame, Wooded Retreat near Road America

The Elkhart A-Frame is an ideal location for the adventure seeker who wants a unique and private experience that is still close to all the action. The home sits on a wooded three-acre private retreat only about a mile from the village of Elkhart Lake, Road America, and Golf Courses. This unique cabin was built in the 1970's but has been recently renovated with a fun Scandinavian modern flair. It has all the amenities for a memorable vacation stay that provides plenty of epic photo opportunities.

Kitchen · Family · Amenities

Peaceful Home in Heart of Oshkosh!

Whether you're planning a weekend escape or an extended stay, this welcoming home has everything you need to relax and settle in. With 3 bedrooms, 1.5 baths, in-unit laundry, a spacious dining area, and a great selection of games & puzzles, it's perfect for families, friends, or business travelers. Located just a 2-min drive to downtown Oshkosh, you’ll be ideally situated to explore the area. Discover local favorites like the EAA Museum, or browse charming shops, restaurants, and cafes nearby.

Family · Indoor spaces · Heating

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.

Indoor spaces · Family · Sleep quality

Go and Go

Cozy 2 bedroom Log home. Can sleep 4-6. Across the street from Lake Winnebago. Short walk to park, zoo and boat landing. 6.5 miles to EAA grounds. Off street parking. Close to shopping, restaurants and downtown Oshkosh. Great rental for Air Show, Book now and bring your boat, jet ski, trailer, and fishing gear or just go sightseeing, dining and relaxing. Full kitchen, New Bath. Very comfortable with a great location. Perfect place to stay for family with students at UWO. Book now!

Kitchen · Family · Access

Secluded Cabin with Sauna

Place yourself in nature. Put down your phone and pick up a book. Clear your mind, focus on your breath, connect with your inner self. Sleep like you’ve never slept before accompanied only by the sound of owls and wind in the pines. The Belden Farm offers land that is a true retreat. Enjoy the privacy and quiet of our cabin in the woods. Extensive, well-maintained trails for hiking, skiing or Fattire biking lead you through towering hardwoods, cathedral white pines, and golden meadows.

Family · Indoor spaces · Comfort

Relaxing Lakefront Getaway on Lake Butte des Morts

Relax at our spacious lakefront retreat on Lake Butte des Morts in a small and friendly neighborhood! Enjoy stunning sunsets, beautiful lake views from the bedroom, living room, and dining area, plus a private pier for fishing and relaxing. Features include a queen Sleep Number bed, gas fireplace, full kitchen, washer/dryer, fire pit, grill, and off-street parking. Near EAA, restaurants, shopping, the Wiouwash Trail, and just 40 miles from Lambeau Field. Longer stays welcome!

Kitchen · Indoor spaces · View

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.

Family · Indoor spaces · Parks

Shorehaven Lakehouse

Welcome to the Shorehaven Lake House! Perfect for a couples retreat, an outing for the entire family, or those in town for any of Oshkosh and the surrounding cities many events! Have the ultimate Wisconsin getaway by escaping to this beautifully renovated Lake Butte des Morts home that comfortably sleeps 6. This home provides beautiful sunsets and sunrises over the lake and a quiet neighborhood for your escape! Please let us know if you have any questions!

Family · Kitchen · Biking

Charming Spacious 2BDR by Downtown/Menominee/Lake

This historic and charming home is located just one block away from Menominee Park and Lake Winnebago. Menominee parks offers amusement rides, the Zoo, asphalt trails, boat tie ups, casting dock, historical interest, fishing, ice rink, picnic areas, large playgrounds, baseball fields, soccer fields, tennis/ pickle ball courts, and volley ball courts. The home boasts a lot of character and has all the amenities to make your stay comfortable and memorable.

Kitchen · Indoor spaces · Parks

Goat Retreat: Petting Zoo, Barn, Hot Tub & River

The Cloverland Barndominium is a thoughtfully renovated 100-year-old barn sitting on 5+ private acres of forest to explore next to a river. You'll share the land with friendly goats that you can watch from right outside your window! Outside you'll enjoy walking the trails, feeding the animals, taking the canoe down the river, making a fire in the fire pit, and exploring the forest. Escape the busy world and reset!

Indoor spaces · Family · River

The Raven | Modern Escape To The Woods

Welcome to The Raven, a modern escape to the woods tucked among towering pines near Hartman Creek State Park. Soak in the private hot tub beneath the stars, gather around the fire pit, hike nearby trails, or unwind with records, movies, and woodland views. Just minutes from the Chain O' Lakes, restaurants, and shops, The Raven combines contemporary comfort with the peace and privacy of the Wisconsin woods.

Kitchen · Family · Hot tub

Rosie's Place A

Hello and Welcome! Rosie's place A features a cozy newly renovated clean furnished upper apartment. Very close to everything in Oshkosh. Great for business travelers, vacationers and visiting University of Oshkosh and Hospital families. Breakfast items, fruit, coffee, tea, soda, water & snacks included. Private parking behind the house. Door code will be provided to enter. No minimum stay!

Kitchen · Indoor spaces · Long stay