Family-friendly holiday rentals in Oshkosh

Linger Longer On The Water

Cozy lake cottage on the west shore of Lake Winnebago featuring 3 bedrooms and 1 bath. Beautiful sunrises over the lake and just minutes from everything in Oshkosh Wisconsin. Large kitchen for preparing meals or just hanging out. 5 minute walk to Menominee Park. 6.5 miles to EAA Grounds. Less than 10 minutes to downtown and the University of Wisconsin, Oshkosh campus, shopping, restaurants and Main Street. Great location for walking, bike riding and just seeing the local sites. Park on site.

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.

Leonard Point Birdhouse

Welcome to the Leonards Point Bird House! This newly renovated lake home has all amenities needed for a perfect escape in Oshkosh, WI. You will experience lake views from the south side of Lake Butte Des Morts. For a quieter experience (or louder for the kids) there is a detached bunk house with its own bathroom! The Birdhouse is 10 minutes away from highway 41 and multiple stores for easy access to everything you need. Please feel free to reach out with any questions!

Cozy Relaxing Lake Home with spectacular sunsets!

On the shore of Lake Butte Des Morts Longer stays welcome!!! Awesome Lake view Beautiful Sunsets Gas fireplace Shopping/restaurants/etc… Approx. 40 miles from Lambeau Field pier/summer,sorry nothing can be tied up to pier at any time solo fire pit grill Lake view Bedroom,Living Room,Dining area Near by Wiouwash trail for hiking, biking, etc.. Near EAA Kitchen space for cooking. Washer/dryer Larger 1 bedroom /Queen Sleep Number mattress Off street parking

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.

The Tree House. Whole house. Enjoy Appleton!!!!

Cozy downtown Appleton home close to everything Appleton has to offer!! Within walking distance to Farmers Market, Fox Performing Arts Center, restaurants and within 30 minute drive to world famous Lambeau Field home of the Green Bay Packers!! Enjoy the tranquil backyard with one of the biggest maple trees in the city, enjoy vintage artwork and spin classic vinyl in the music room. Fall 2025 just around the corner. The house is yours! No other guests.

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.

Freshly Renovated, Modern House - Great Location

-Historic residential district near downtown, Lawrence University, the Performing Arts Center, Mile of Music and more - great location but still VERY quiet area. -30 minutes to Green Bay and Oshkosh -3 season porch -New deck overlooking wooded backyard -Safe, well established neighborhood with tree-lined streets and beautiful parks -Need more space or traveling with friends? Click Visit our profile to see our additional 5★ Appleton properties

No Cleaning Fees! 2 Bedroom Apartment By The Lake

We’re transparent with our pricing, that’s why we don’t have cleaning fees! The price you see is the price you pay (local taxes still apply). Come stay near the heart of Oshkosh - you’ll be on the second floor with views of Lake Winnebago. If you need anything during your stay we live on-site and are only a message away. Don’t worry though, the units are completely separated so you’ll have all the privacy you desire during your stay.

Barndominium with Goats, Hot Tub, Forest & 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 and chickens 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!

Cozy Retreat • Fireplace Loft •Walk to Park & Lake

🍁 Cozy 3BR family retreat across from Menominee Park & Lake Winnebago! Enjoy fall walks to the beach, zoo, and trails—all just steps away. Minutes from downtown Oshkosh, including dining and shops. Features a new upstairs lounge with large TV and fireplace, king suite, and basement bar—perfect for family time and Thanksgiving gatherings. Includes driveway parking and easy self check-in for a smooth stay.

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!