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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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!

LocationValueOutdoor spaces

4.94 out of 5 average rating, 93 reviews

Guest favorite

Home in Poynette

Cozy Cabin on Crooked Lane close to Lake Wisconsin

Nestled in a quiet, woodsy neighborhood, this cozy cabin offers everything you need for a relaxing getaway — fire pit, propane grill, fenced dog-friendly yard, high-speed WiFi, two large smart TVs, & a mini air hockey table. You’ll be just a short walk from Lake WI, with public boat launches, trails, and playgrounds nearby. Spend the day boating, fishing, or exploring local spots like the Mackenzie Center, or take a quick drive to Devil’s Lake or Wisconsin Dells for even more outdoor adventure.

ValueLocationGetting around

4.89 out of 5 average rating, 55 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.

FamilyValueLaundry

4.96 out of 5 average rating, 135 reviews

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.

ValueLocationAccuracy

4.93 out of 5 average rating, 121 reviews

Guest favorite

Home in Wisconsin Dells

16ppl | Sauna. Hot tub. Theater. Games on 5 acres

Sleeps 16. Set 8 minutes from downtown Wisconsin Dells on 5 acres with towering pines, it is a majestic escape in nature but close to it all! Relax in the infrared sauna with loungers while the children play the arcade games steps away from the private in home movie theater where you can stream your favorite movies or sports game! There are trails throughout the back of the property and a wonderful fire pit off of the back deck! Spacious and comfortable for the entire family or group!

FamilyLocationNearby

4.97 out of 5 average rating, 102 reviews

Top guest favorite

Cottage in Portage

Modern Riverview Cabin Near Devil’s Lake

Reconnect w/ nature in this beautiful modern cabin set on 2 acres overlooking the WI River. Located near Devil's Lake, WI Dells, Devil's Head and Cascade ski resorts, it is the perfect place to unwind. Bedrooms have a king bed, queen bed and four bunk beds - each w/ ensuite bathrooms. Given the bedroom w/bunk beds, we approve 6 adults or up to 8 if 2 are children. Enjoy camp fires around a Solo Stove and grilling on the charcoal Solo Stove Grill. This cabin is new w/new furnishings.

FamilyLocationGetting around

5.0 out of 5 average rating, 91 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.

LocationFamilyComfort

4.94 out of 5 average rating, 127 reviews

Top guest favorite

A modern kitchen is presented with light-colored cabinets and dark countertops. Stainless steel appliances are visible, including a refrigerator and an oven. The spacious island features seating for two, while pendant lights hang above, providing ample illumination. A clock adorns the wall, adding to the functionality.

Home in Poynette

Private, Modern, Cozy Country Home

This is a very private and quiet new home in the country on 53 acres of land. Perfect for a family getaway or romantic getaway. There are many areas to explore on our land, including wooded trails. XC ski or snowmobile in winter. Enjoy the privacy of having a country home to yourselves, but only short drive to restaurants, shopping, a winery, or Cascade Mountain Skiing. Pickleball courts nearby! We are a 30 minute drive to Madison, Wisconsin Dells, or Devil’s Lake in Baraboo.

LocationFamilyQuiet

4.98 out of 5 average rating, 60 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.

FamilyLocationAmenities

4.99 out of 5 average rating, 68 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!

LocationFamilyHiking

4.92 out of 5 average rating, 283 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.

LocationValueHiking

4.99 out of 5 average rating, 165 reviews

Guest favorite

The cozy cottage exterior features light-colored siding and large windows, allowing for natural light. A wooden deck with chairs provides a spot to enjoy the view. A serene sunset over the lake with reflective water complements the tranquil surroundings.

Cabin in Pardeeville

Cozy Lake View Retreat

A perfect spot to escape! Just a short stroll to Park Lake with stunning sunsets. Our cozy cottage/lake view is just what you need to relax and unwind after the day's adventures. A stocked kitchen/LR with coffee, games, DVD player, DVD'S, 40” smartTV. Prime location to all things fun! Lake activities, hiking, exploring in the summer and ice fishing, downhill skiing and snowmobiling in the winter! We love sharing our space and know you will love it just as much.

LocationFamilyHeating

4.81 out of 5 average rating, 37 reviews