Family-friendly holiday rentals in Columbia County

Lake Wiscosnin Cozy Cottage

Relax and unwind at this cozy cottage on the Wisconsin River with fantastic views. Enjoy the park right across the street with fishing, a picnic pavilion, beach and playground for your kids. Public boat launch is only a block away. Full laundry and eat in kitchen features quartz counter tops and makes you feel like you're home away from home. Many local restaurants and bars within driving distance, as well as wine tasting and 2 ski resorts. Keurig and a propane grill provided. CableTV and Wifi

Cottage Near Devil's Lake

Perfect Location! Under ten minutes to almost everything. Our cozy and romantic getaway is nestled in the scenic Baraboo Bluffs, just minutes to Devil's Lake, Devil's Head Resort, Historic Downtown Baraboo, wineries, distilleries & more. Take the picnic set to Devil's Lake or Parfrey's Glen, then relax on the patio for smores and yard games around the fire pit. Finish the evening snuggled up with wine & vinyl on the player. We have ample parking so bring the boat, we'd love to help you getaway.

Comfy Nook, 5 Miles from Cascade Mountain

This apartment has two bedrooms and one bath. Located in downtown Portage, just 20 minutes from Wisconsin Dells easy access to the interstate. Cascade mountain just a few minutes away. There is a driveway for off-street parking for two cars. There is a private outside stairwell entrance and keypad door lock for access. This apartment is older construction and is on the 2nd floor. The floors are squeaky and noise will carry to the lower unit. Quiet time at 10:00pm. Just a short walk to downtown.

The Bobber Simple Cabin -Quaint 1BR/1BA-perfect HQ

This cottage is located in a beautiful rural setting. Set back off the main street with a private dead-end gravel drive. It's quiet and dark - perfect for stargazing. This is a simple, clean, and affordable space for those who are looking to get closer to nature. Conveniently located nearly equidistant to Madison, Wisconsin Dells, and Devil's Lake State Park. A wonderful HQ for exploring the natural beauty of Driftless Wisconsin. Plenty of hiking, skiing, breweries, wineries, and agri-tourism.

Secluded WI River Getaway w/ Hot Tub near Skiing

Get away from daily routines & refresh by the Wisconsin River at your private & peaceful retreat located near Devil's Lake, Cascade Ski & Devil's Head Ski/Golf Resorts & WI Dells. Perfect for families w/ 9 beds, 8 person Hot Tub, 6 Kayaks (May-Oct), Ping Pong, Foosball, Darts & Outdoor Games. The modern spacious design is filled w/ natural light, luxury comforts & new furnishings w/ Chef’s Kitchen, Weber Grill, Fireplace & Solo Stove. Ask us about nearby River Islands or day trips to ski/hike.

NEW Hot Tub! Perfect Location, Downtown Baraboo

Welcome to this thoughtfully renovated 80-year-old home that lives in the heart of Baraboo. With its perfect blend of vintage charm and modern comfort, this adorable home will be the perfect getaway. From being in the perfect neighborly location between Wisconsin Dells and Devils Lake State Park you have endless options to cater to any of your desires. You are only: 2 min to Downtown Baraboo 4 min to Circus World 11 min to Devils Lake 18 min to Wisconsin Dells 18 min to Cascade Mountain

Quietwater Cottage-Hot Tub, Nearby Skiing, Nature!

Hot Tub on deck with sunset and water view! Near Cascade Mountain Ski Resort, Devilshead, Christmas Mountain!!! XC skiing nearby at Mirror Lake State Pk & Lodi Ski Trails. Great place to come back to after a day of skiing for a soak with a GREAT view of nature! Conveniently located on the Lake Wisconsin waterfront between Madison and the Wisconsin Dells, just 1.5 hours from Milw and 3 hours from Chicago. We are pet friendly for well behaved dogs with a $25/night pet fee per dog.

Lakeview Cabin> Unique Mid-Century Tucked in Bluff

Nestled in the bluffs of Caledonia, this cabin offers a true Wisconsin experience! Floor to ceiling windows boast amazing water views of Lake Wisconsin, all while you reside in the charm of the mid-century architecture of this cabin. Minutes from the bluffs of Devil's Lake which offer some of Wisconsin's best hiking, biking, walking trails, and swimming! Plus, a short drive from Baraboo or Wisconsin Dells, where you can check out shops, restaurants and local attractions!

Real Christmas Tree Farm! Skiing nearby

Get lost in nature and stay where the magic grows on a real Christmas tree farm! Situated on rolling hills below the Baraboo bluffs, this 125 acre farm and nature preserve has several miles of hike/bike/ski trails, a private lake and two creeks. Modern home in a quiet rural neighborhood. Easy drive on beautiful country roads to the many attractions in the area--less than 10 minutes to Devil's Lake State Park, Lake Wisconsin as well as Devil's Head & Cascade ski areas.

Green Door Getaway

Take a moment. Make yourself a cup of coffee in the bright kitchen. Find a cozy corner to read a good book. Grab the yoga mat and get your workout in while you stay. Spread out at the desk and finish your project. Connect with family and friends in the spacious living and dining areas. Enjoy a hike at a nearby State Park. Take in the thrills in the Dells. Ski down Christmas Mountain, Devil's Head or Cascade. Maggie's Green Door Getaway is ready for you to enjoy!

Perfect for all Seasons, Top Amenities close by!

Parfreys Glen, Devil's Lake, Devil Heads Resort....We are right next to all of these very popular destinations! A few are even within walking distance! Located on just under 3 acres we have a beautiful home here in the country that we call the Chateau. Below us we have added a brand new, 2 level, spacious apartment. The apartment features a full bathroom on each level as well, a full kitchen and a deck with a spectacular view to relax and unwind.

Orchard Prairie B&B

Welcome to my home - Orchard Prairie Air B&B! This unique space was built by an amateur pilot, "MacGyver-Type," Renaissance Man roughly 30 years ago. It is set on 38 acres of pristine Wisconsin Land and is perfect for nature lovers and "Glampers" looking for the great outdoors with the comforts of home. It is a "rustic-industrial" oasis in the heart of South Central Wisconsin, steps from Devils Lake and miles from Baraboo and the Wisconsin Dells.