Family-friendly vacation rentals in Winnebago County

A spacious dining area features a large wooden table surrounded by six chairs, accommodating family meals or games. Two green armchairs are positioned in the corner near a wall clock and framed world map, while natural light fills the room through multiple windows.

4.9 out of 5 average rating, 110 reviews

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.

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4.94 out of 5 average rating, 126 reviews

Birdhouse | Lakefront • Private Dock • Bunkhouse

Welcome to the Birdhouse, a private lakefront getaway on Lake Butte des Morts in Oshkosh! Enjoy your own dock, waterfront yard, lake views, and a separate one-bedroom/one-bath bunkhouse just steps from the main home. With 3 bedrooms and 3 bathrooms across the property, the Birdhouse is great for families, multiple couples or groups who want to vacation together while still having their own space! Come home to a beautifully renovated house that's just minutes from Oshkosh and Hwy 41 :)

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A log home with a wooden exterior is surrounded by lush greenery. The front porch is adorned with a small blue umbrella and features a set of steps leading to the entrance. Gravel driveway and flower beds enhance the welcoming ambiance of the property.

4.88 out of 5 average rating, 223 reviews

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!

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4.99 out of 5 average rating, 152 reviews

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 (seasonal)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!

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4.96 out of 5 average rating, 204 reviews

Guesthouse in Oshkosh

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.

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4.96 out of 5 average rating, 338 reviews

Cabin in Winneconne

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!

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4.91 out of 5 average rating, 323 reviews

A cozy sleeping area contains two full-size beds adorned with warm-colored bedding. Nightstands with lamps are placed beside each bed. A comfortable chair sits in the corner, and two windows allow natural light to illuminate the room. Decorative rugs cover the laminate flooring.

Apartment in Oshkosh

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! NO CLEANING FEE!

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A dining area features a large wooden table surrounded by six wooden chairs, situated on polished hardwood flooring. Natural light enters through two windows adorned with sheer curtains. A wooden accent wall adds texture, while a simple chandelier provides overhead lighting.

4.77 out of 5 average rating, 144 reviews

The Parkway Paddle: Walking distance to the lake

Stay within walking distance of Lake Winnebago in the heart of Oshkosh at the ‘Parkway Paddle’. The property is next to Menominee Park, which is surrounded by water and the perfect place to watch the sunset. The park also has a zoo with free admission. The historic home has been upgraded with granite countertops and luxurious lakeside and paddle-boat touches throughout the home.

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A contemporary two-story home is set against a vibrant green lawn. The exterior features dark siding complemented by large windows and a welcoming front entrance. Surrounding trees and open space enhance the peaceful atmosphere of the property.

4.93 out of 5 average rating, 138 reviews

The Harbor Hideaway

Escape to your dream vacation in this 4-bed, 4-bath haven surrounded by tranquility. The chef's kitchen, equipped with modern appliances, caters to culinary delights. Each bedroom, featuring plush bedding and thoughtful furnishings, offers a retreat with a mix of king and queen-sized beds. Four bathrooms ensure convenience and privacy.

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The home exterior is characterized by a gray siding, complemented by a steep roof and multiple windows. A welcoming front porch is accessed by a set of stairs. Colorful flower beds and planters are positioned around the entrance, adding natural beauty to the landscape.

4.88 out of 5 average rating, 156 reviews

Cozy getaway 1 mile from downtown and UWO campus!

2 bedroom home with a living room and dining room, kitchen with appliances, laundry room and Big backyard. (Kid friendly) Grocery store, gas station, and restaurants are less than a mile away. (Within walking distance) Great, clean neighborhood. Only a mile from Menominee park, arena, and other destinations you may want to explore.

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A welcoming living area is highlighted by a brown sofa and an armchair. Light floods in through two windows, casting shadows on the hardwood floor. Notable art pieces are displayed on the wall, and a small side table with a lamp adds to the cozy ambiance.

4.9 out of 5 average rating, 167 reviews

Waterfront Retreat @ Oshkosh’s Sawyer Creek

Relax with the whole family at this peaceful 3 bedroom waterfront home. This home is adjacent to “West Algoma Park” one of Oshkosh’s many parks. Within walking distance to UWO campus, Paine Art Center, Fox River Brewery and Oshkosh Corp Headquarters. For business or pleasure this home will fulfill all your needs.

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