Family-friendly holiday rentals in Calumet County

Family lake retreat w/ hot tub! Amazing sunsets!

Lakeland Retreat has 4 bedrooms, den and plenty of entertaining space! Directly on Lake Winnebago with private pier and AMAZING sunsets! Bring your boat and launch nearby, launch is 5 min away. Our spacious outdoor area with double swing for relaxing by the lake, dining table, firepit and hot tub. Great entertainment space indoors with a living room right off the kitchen with lake views. Cozy up by the fireplace indoors too! Full bar area and pool table in the basement! Great family fun!

The Farm Unique Rural Lodging

Your accommodations are the entire second floor, with a private entrance and deck to enjoy the sunrise or just relax. The Farm is peaceful offering access to our 100 acres. Our suite has three separate bedrooms, a common area, a micro kitchen and private bathroom. We have a 6 guest limit with a 4 adult max. Published pricing reflects the cost for two guest, each guest after two has a $20 nightly fee. We have a no pets, no smoking or vaping policy. Booking guest must be present during stay.

State Park Getaway with Hot Tub & Arcade

This fully remodeled A-Frame is walking distance to hiking trails and has views of Lake Winnebago. The outdoor enthusiast will find endless opportunities for adventure (canoeing, hiking, fishing, snowshoeing, biking) at High Cliff State Park. Take in the forest views from your private backyard with a large hot tub, fire pit, or relax on the private deck with stunning views of Lake Winnebago. Create memories with the private hot tub, giant chess board, arcade, and huge selection of games.

Newly Built Brillion Townhouse

Come & enjoy a newly built townhouse that is fully furnished for an easy stay! Located in Brillion, it is central to Manitowoc, Green Bay, and Appleton (about 25 min to each & 40 min to Lambeau Field!). Enjoy many amenities like zoned in-floor heat, wall air, Zero entry (no steps), attached 2 car garage, patio, park views, open concept w/full & large kitchen, dining & living room. Dual entry full bath, in-unit washer & dryer. Minutes to Ariens Nordic Center. 40 min to Lambeau Field!

New! Lake Front|PrivateDock|Kayaks&Paddleboards!

Enjoy Lake Winnebago at this cozy newly furnished lakefront home. It sleeps 7, and includes a fully stocked kitchen. Enjoy the deck facing the lake with chairs and a propane grill—perfect for outdoor meals or a cup of morning coffee from the coffee bar! Spend your days kayaking, paddleboarding, swimming, or fishing from the private dock. Just 15 minutes from Chilton and under an hour from Green Bay, it’s a perfect spot for families or friends to relax and enjoy the lake!

Parkside Retreat | Minutes from Elkhart Lake

Parkside Retreat is located in the quaint city of New Holstein, right on the city’s largest park. The Aquatic Center, basketball/tennis courts, ball diamonds, fishing pond, and walking paths are located just steps outside. Just 10 miles away from Elkhart Lake and Road America we are close to everything yet tucked away from the crowds. Enjoy all that this beautiful area has to offer, then settle in for a relaxing evening at Parkside Retreat. PET FRIENDLY - 1 pet limit

High Cliff Hideaway

Feel at home in this quiet and safe neighborhood. Only 20 minutes from the city, making it a convenient place to rest your head outside of the craziness of the city lights. 15 miles to Appleton/Fox Cities Performing Arts Center/Airport 30 miles to Green Bay/Lambeau field 33 miles to Oshkosh/EAA Air Venture Less than 2 miles from High Cliff State Park/ High Cliff Golf Course/ Lake Winnebago

Cozy with Thoughtful Design

Welcome to your cozy two-bedroom, one-bathroom apartment nestled in a convenient, centrally located neighborhood. As you step inside, you're greeted by a spacious living area adorned with modern furnishings, designed to provide both style and comfort. Sink into the plush sofas and unwind after a long day, or gather around the sleek smart TV for a movie night with friends and family. .

Harsch's Beach Escape | Lake · Hot Tub · Theater

Welcome to Harsch’s Beach Escape Luxury lakefront living on Lake Winnebago! • 175' private shoreline + boat dock • Rooftop deck with sunset views 🌅 • Hot tub overlooking the lake • Private movie theater + PS5 🎮 • Rock wall & Ninja ropes course • Kayaks & paddleboards included • Sleeps 12 MAX · 4BR · Family-friendly Book your unforgettable stay with Wisconsin Getaways!