Family-friendly holiday rentals in Columbia County

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Top-rated family-friendly rentals in Columbia County

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

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Guest favourite

Home in Pardeeville

4.92 out of 5 average rating, 142 reviews

5BD/Sleeps 12-Relax by the lake or wander to town

Create wonderful family memories year round - hang by the lake, around the campfire, fish, paddle, have a movie or game night in or take a soak in the hot tub that over looks the lake. Stay in or go out there’s so many options. Games, puzzles, books, movies, cozy spots to curl up with a good book + a wonderful backyard with a fire pit. This house has so much to offer - we put a lot of thought and love into making your stay comfortable and relaxing. We truly hope you enjoy it as much as we do.

Guest favourite

Cottage in Poynette

4.96 out of 5 average rating, 234 reviews

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

Top guest favourite

Home in Baraboo

4.96 out of 5 average rating, 123 reviews

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.

Guest favourite

Home in Poynette

4.92 out of 5 average rating, 197 reviews

Island View Hideaway-Peaceful, On Water, Sandbars!

Rent this furnished cottage to enjoy the beauty of nature on the Wisconsin River and Lake Wisconsin. 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. Beautiful views out the large living room windows look onto green, sandbars, islands and the undeveloped distant shores of the Wisconsin River as it opens up into Lake WI.

Superhost

Guest suite in Poynette

4.9 out of 5 average rating, 123 reviews

Lake Wisconsin 2BR* GreatHiking nearby -Water View

Come to relax, hike, or simply enjoy nature. It's located at the eastern tip of Lake Wisconsin. It is a clean space that is great for families. Enjoy the amenities of having a fully furnished home with some of the best views in Wisconsin. Great location that is nearly equidistant to Madison, the Dells & Devil's Lake. It's a great hub for hiking with the following all within 15 - 35 minutes: Devil's Lake, Parfrey's Glen, Gibralter Rock (ice age tr), Mackenzie Center, Lodi Marsh & Mirror Lake.

Guest favourite

Home in Portage

4.95 out of 5 average rating, 111 reviews

Grandma's House: Summer Vacation Time!

Welcome to Grandma's House, a single level home nestled in the beautiful hills of Caledonia, between Portage and Baraboo. Three bedrooms, sleeps 8, full kitchen, dining room, living room and an attached 2-car garage. Just 4 miles from I90/94, Grandma's House enjoys easy access to Portage, Baraboo and Wisconsin Dells. 2023 renovations include, new vanity mirror in bathroom, new queen hide-a-bed with memory foam mattress (no bar at the back), and new queen bed with pillow- top mattress.

Guest favourite

Cabin in Merrimac

4.91 out of 5 average rating, 199 reviews

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!

Top guest favourite

Cabin in Baraboo

4.98 out of 5 average rating, 348 reviews

Private Baraboo Bluffs Cabin with Peacocks!

This is a beautiful getaway surrounded by nature. It’s on 180 acres with walking trails. The vibe is unbeatable. You will find your peace. Hike! Relax in nature! Way up in the Baraboo bluffs and right by some of Wisconsin's favorite attractions. Minutes away from Devil’s Lake, ski hills and great hiking. Relax by the fire surrounded by nature. Nature therapy! Forest, wildflowers, and peacocks right out your window. Dogs allowed with prior approval but no other pets

Top guest favourite

Home in Merrimac

4.98 out of 5 average rating, 109 reviews

Real Christmas Tree Farm! Devil's Lake 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.

Top guest favourite

Home in Baraboo

4.9 out of 5 average rating, 113 reviews

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!

Guest favourite

Guest suite in Wisconsin Dells

4.84 out of 5 average rating, 543 reviews

Spacious 2 Bedroom - 8 Complimentary Park Passes!

Welcome to Wisconsin Dells and the city of Baraboo, a popular vacation playground best known for its beautiful river scenery, endless entertainment options and larger-than-life water parks. Inside the Wilderness Territory a theme park where family fun reign supreme is a top ranked indoor and outdoor water park. You can also find some excellent shopping, visit wineries for tastings, practice your swing on local golf courses, and win big at Ho-Chunk Casino.

Superhost

Guest house in Pardeeville

4.84 out of 5 average rating, 115 reviews

Park Lake Cottages in Pardeeville Wi

A little slice of heaven right on Park Lake in Pardeeville, WI. Located just one mile from downtown Pardeeville, thirty miles north of Madison and roughly thirty miles east of Wisconsin Dells. This is a 3 bedroom cabin where you can enjoy campfires, fishing, swimming, and boating from the piers. Also, the sunsets do not disappoint! Local attractions include; dining at The Caddy Shack or The Upper Crust and be sure to visit Carol's Cones for desert!