Vacation rentals in Columbia County

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Top-rated vacation rentals in Columbia County

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

A charming yellow house features a welcoming front porch with large windows and a decorative entry door. The well-maintained garden includes colorful flowers along a paved walkway. An American flag is displayed proudly beside the entrance, complemented by a grassy yard and mature trees in the background.

Home in Pardeeville

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.

4.93 out of 5 average rating, 155 reviews

Guest favorite

Aerial view of a house nestled among dense green trees, showcasing a red roof that contrasts with the surrounding foliage. The property is partially visible, with a patio area indicated by an outdoor table and chairs situated near the home.

Home in Portage

*NEW OWNR SPECL Private Getaway w/ Sauna + Hot Tub

Atop the hills of the Town of Caledonia surrounded by woods, a true escape for some R&R. Some of the best skiing in the area, both Cascade Mountain & Devil's Head within minutes! Expansive floor-to-ceiling windows w/sunset views. Outdoor spaces surrounded by nature, indoor hot tub & sauna, plus rec area for enjoying games by the LL wet bar. Covered patio & firepit to warm up. Close to WI Dells, Baraboo, Portage, a perfect retreat for a peaceful getaway for the whole family or a romantic getaway!

4.95 out of 5 average rating, 92 reviews

Top guest favorite

A cottage is nestled within a wooded area, featuring light-colored siding and a green roof. A wooden deck leads to the entrance, surrounded by autumn leaves and natural landscaping. Windows allow natural light to illuminate the interior, creating a warm and welcoming exterior.

Cottage in Poynette

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

4.96 out of 5 average rating, 265 reviews

Top guest favorite

The open living area features high ceilings and large windows that allow natural light to fill the space. A green sectional sofa and matching ottoman are arranged around a coffee table. A wooden dining table is visible in the background, along with a modern kitchen.

Cabin in Portage

Secluded WI River Getaway w/ Hot Tub near Golfing

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.

4.95 out of 5 average rating, 132 reviews

Top guest favorite

A spacious cabin is pictured against an expansive lawn, surrounded by verdant trees. A stone chimney rises prominently against the sky, which is covered with a mix of soft clouds and a hint of sunlight. The serene landscape evokes a sense of tranquility.

Cabin in Merrimac

Enjoy a secluded cabin with epic sunsets & horses

An enticing retreat nestled in the heart of Wisconsin’s hidden gems. 3 miles from Devil’s Lake State Park, plenty of local eateries nearby, and Devil’s Head Ski Resort located across the street. There’s no shortage of opportunities for family time & adventure. Wisconsin Dells is 20 minutes away. Bring the whole family to this spacious getaway, located on a horse ranch in the quiet, secluded area of Merrimac, WI. Take the ferry for ice cream, and fish off the dock for a fresh, relaxing dinner.

4.93 out of 5 average rating, 120 reviews

Guest favorite

A spacious dining area features a wooden table set for six, adorned with lace placemats and a floral centerpiece. The open layout leads to a cozy living room, highlighted by comfortable seating and large windows allowing natural light to brighten the space.

Home in Portage

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. 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.

4.94 out of 5 average rating, 126 reviews

Top guest favorite

Cabin in Lodi

Private Resort Cabin | Pool • Hot Tub • Sauna

Escape to your own private resort in the Wisconsin countryside. Set on 8.43 peaceful acres, Wanderlust Cabin brings together the warmth of a true log home with everything you need for an unforgettable getaway—private heated pool, 8-person hot tub, outdoor sauna, firepit, fireplace and beautiful spaces to gather. Secluded enough to truly unwind, yet just minutes from Lake Wisconsin, hiking trails and downtown Lodi, with skiing, wineries, dining and plenty to explore nearby.

4.98 out of 5 average rating, 66 reviews

Guest favorite

Cabin in Merrimac

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!

4.92 out of 5 average rating, 278 reviews

Guest favorite

A cozy nook features a large window adorned with a stained glass design, allowing natural light to fill the space. A plush armchair sits beside a simple blue table, while a window seat is decorated with soft cushions, inviting relaxation in a wooden interior.

Cabin in Baraboo

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

4.97 out of 5 average rating, 403 reviews

Top guest favorite

A scenic view showcases the modern home nestled among vibrant trees on a Christmas tree farm. Rolling hills are seen in the background, adorned with foliage in shades of red, orange, and green. Neatly arranged rows of Christmas trees line the foreground.

Home in Merrimac

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.

4.99 out of 5 average rating, 161 reviews

Top guest favorite

A dining area features a light wood table surrounded by six chairs, positioned beneath a modern light fixture. Green walls offer a warm contrast to white accents. A decorative centerpiece holds plants, while large windows allow natural light to illuminate the space.

Home in Baraboo

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!

4.93 out of 5 average rating, 168 reviews

Guest favorite

A cabin is situated on a grassy area by Park Lake, with tall trees providing shade. A small dock extends into the water, and a modest boat is visible nearby. Nearby, a picnic table and fire pit are set up, creating a leisure-friendly atmosphere.

Guesthouse in Pardeeville

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!

4.85 out of 5 average rating, 133 reviews