Family-friendly vacation rentals in Oshkosh

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.

4.91 out of 5 average rating, 107 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.

FamilyKitchenSleep quality

5 out of 5 average rating, 178 reviews

Home in Appleton

Appleton Wooded Oasis - Hot Tub-6 Star Hospitality

Relax and enjoy in a beautiful scenic home conveniently located in a quiet wooded neighborhood in Appleton. It has all the elements of being your get away from home. Nearly 3,000 sq. ft. Guests have access to all living areas, modern kitchen, wood fireplace, vaulted ceilings, spacious sunroom, large deck and therapeutic hot tub. Enjoy the scenic backyard with a large deck, 7 person hot tub and fire pit. Five minutes from airport, vibrant downtown, 25 min. to Lambeau. Includes breakfast.

KitchenIndoor spacesGetting around

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, 221 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!

FamilyIndoor spacesAccuracy

4.99 out of 5 average rating, 135 reviews

The exterior of a cabin is depicted, featuring large windows framed by wood. Warm light emanates from within, revealing a cozy interior with a lamp and seating. Snow covers the ground, and icicles hang from the roof, creating a serene winter scene.

Cabin in New London

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.

Indoor spacesFamilyBathroom

4.99 out of 5 average rating, 148 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 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!

KitchenIndoor spacesBackyard

4.96 out of 5 average rating, 203 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.

FamilyIndoor spacesOutdoor spaces

A spacious dining area is illuminated by natural light from large windows. A wooden table with six chairs is centered in the room. Decorative items, including wall art and a wreath, are displayed on the walls, contributing to the charming ambiance.

4.91 out of 5 average rating, 254 reviews

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.

FamilyKitchenComfort

4.86 out of 5 average rating, 276 reviews

The exterior of a two-story house is shown, featuring a porch and a well-maintained lawn. Large windows are visible, offering natural light to the interior. Surrounding trees provide shade, and a pathway leads to the entrance, enhancing accessibility.

Apartment in Oshkosh

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.

KitchenFamilyAccess

4.96 out of 5 average rating, 330 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!

Indoor spacesFamilyComfort

4.91 out of 5 average rating, 316 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!

Indoor spacesFamilyWalkability

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, 149 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.

KitchenIndoor spacesQuiet

A spacious dining area showcases a large wooden table accompanied by industrial-style stools. Above, a ceiling fan circulates air, while a framed artwork of airplanes adds a thematic touch to the wall. A small plant centerpiece brings a hint of greenery to the table.