Family-friendly vacation rentals in Oshkosh

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Top-rated family-friendly rentals in Oshkosh

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Farm stay in New London

4.97 out of 5 average rating, 168 reviews

Irish Acres Farm"Glamping" FAIRY CABIN tiny home

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.

Oct 6 – 13

R1,531 ZAR per night

Guest favorite

Home in Green Bay

4.92 out of 5 average rating, 283 reviews

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!

May 27 – Jun 3

R1,383 ZAR per night

Guest favorite

Cottage in Fond du Lac

4.97 out of 5 average rating, 236 reviews

Cozy Guest House with Lake views.

Our remodeled two bedroom Guest House is adjacent to our Cottage and offers beautiful lake views. Access to Lake Winnebago available at near by boat launches. 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 bed and 2 twin beds, 1 full bathroom, and a fully stocked newly remodeled kitchen. Perfect getaway for some R&R with family or friends.

Sep 30 – Oct 7

R1,234 ZAR per night

Guest favorite

Home in Scandinavia

4.94 out of 5 average rating, 143 reviews

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.

Jan 15 – 22

R1,555 ZAR per night

Guest favorite

Guesthouse in Oshkosh

4.95 out of 5 average rating, 170 reviews

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.

Jun 1 – 8

R3,312 ZAR per night

Guest favorite

Home in Glenbeulah

4.98 out of 5 average rating, 112 reviews

Stay at Sunrise LLC, Like being at Grandma's

Welcome to Stay at Sunrise LLC. We offer a clean and comfortable home for your vacation enjoyment. We are in a rural farm area, the recreation trail head is 3 miles east of us as well as the Wade House, we are near the Kettle Moraine State Forest and the Ice Age Trail and 7 miles from Road America. Large yard, Fire pit, picnic table, child swing set. Garage parking on site if arranged in advance. Smoking is allowed outside of the home. No pets allowed.

Sep 19 – 26

R1,630 ZAR per night

Guest favorite

Cottage in Fox Lake

4.85 out of 5 average rating, 285 reviews

The Little White Cabin, Fox Lake WI

****As of October 15, 2023, all of the piers are out of the water for the winter season.**** 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!

Feb 2 – 9

R2,508 ZAR per night

Guest favorite

Apartment in Waldo

4.98 out of 5 average rating, 259 reviews

The Blue Cobb House

My place is close to 20 minutes south of Elkhart Lake and Road America. You’ll love my place because of the outdoors space, the comfy bed, and the kitchen. My place is good for couples, solo adventurers, and business travelers. The Blue Cobb House is about 15 minutes from Kohler-Andrae State Park and 30 minutes from Harrington Beach State Park. The Kettle Moraine area is just to our west and it is filled with hiking trails.

Mar 31 – Apr 7

R2,013 ZAR per night

Superhost

Home in Poynette

4.86 out of 5 average rating, 227 reviews

Quietwater-Hot Tub, Peaceful, On Water, Sandbars!

Hot Tub on deck with sunset and water view! Enjoy the beauty of nature on the Wisconsin River and Lake Wisconsin in this rustic, yet cozy river/lake cottage. Conveniently located on the Lake Wisconsin waterfront between Madison and the Wisconsin Dells, just 1.5 hours from Milw and 3 hours from Chicago. Peaceful with GREAT VIEWS ACROSS THE WATER! We are pet friendly for well behaved dogs with a $25/night pet fee per dog.

Oct 18 – 25

R3,875 ZAR per night

Guest favorite

Guest suite in Appleton

4.94 out of 5 average rating, 108 reviews

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. Spacious, lower half of our split-level home with 2 bedrooms (queen & double/single), 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.*

Jul 2 – 9

R1,849 ZAR per night

Guest favorite

Apartment in Port Washington

4.92 out of 5 average rating, 250 reviews

Homeport

The apartment is a remodeled former "Summer Kitchen" in the lower level of our cream city brick home. We are located in the heart of downtown next to the marina, close to parks, steps away from restaurants, coffee shops & bars. Lake Michigan is just outside the door! We invite couples, solo adventurers, and business travelers for short and long-term stays.

Sep 24 – Oct 1

R1,841 ZAR per night

Guest favorite

Cottage in Neenah

4.95 out of 5 average rating, 434 reviews

Lake Life, year round hot tub!

Scenic Lake Winnebago located on beautiful Cowling Bay, a great place to stay anytime of the year! Great fishing year round! Awesome outdoor hangouts for a fun & relaxing vacation! Located in the country but just minutes from town! Follow lakelife1591 on Instagram for latest updates!

Nov 14 – 21

R5,981 ZAR per night