House holiday rentals in Columbia County

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Popular amenities for Columbia County house rentals

House rentals with a pool

Home in Wisconsin Dells
4 out of 5 average rating, 8 reviews

Gigantic Waterfront Villa (700)

KatelynnRating, 5 stars9 months ago
Property was right off the water and we absolutely loved being able to swim in the lake.
Home in Wisconsin Dells
4.79 out of 5 average rating, 235 reviews

Tree House Home

KimberlyRating, 5 stars2 weeks ago
A wonderful experience! Rich's place is warm, comfortable, spacious, and inviting. The location, amenities, and cleanliness are top-notch. Rich is very responsive and took great care to ensure we had all the information we needed for our visit. The kiddos absolutely loved the playroom with games and a fun loft area. We were just minutes away from all the excitement and attractions of Wisconsin Dells, yet the home itself felt tucked away, like a peaceful retreat from the hustle and bustle. An excellent choice for anyone planning to visit the Wisconsin Dells area, and we thank Rich for helping us make the most of our weekend getaway! Thank you, Rich!
Home in Wisconsin Dells
4.29 out of 5 average rating, 7 reviews

10 Person Lakefront Villa on the Lake Delton (720)

DaynaRating, 5 stars10 months ago
Excellent, clean cottage right on lake Delton! Beautiful beach, live music, pontoon rentals, pool, so much to do for kids and adults! Right by Noah’s Ark! Wonderful place for families!
Home in Poynette
4.81 out of 5 average rating, 47 reviews

Your Home Away From Home!

MoiraRating, 5 stars2 months ago
This was our third time staying at this house and it was still easy, convenient, and with everything we needed. The location is great for accessing some of the local ski resorts, and there were enough bedrooms and space to accommodate three families and a gaggle of kids. The whole process was easy and Brittney was responsive and helpful the whole time. Looking forward to returning next year!
Superhost
Home in Portage
5 out of 5 average rating, 4 reviews

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

AnthonyRating, 5 stars3 months ago
This house was incredible! There was tons of space, and the kitchen had everything we needed. We brought 4 children, and the layout of the house was perfect for naptimes. We were a 20 to 30-minute drive from skiing, restaurants, and other outings. We were there during an incredibly cold weekend, but we could imagine how fun it would be to stay there in the warmer months with the pool and outdoor area!

Weekly house rentals

Top Guest favourite
Home in Wisconsin Dells
5 out of 5 average rating, 25 reviews

The Hillside B&B. Home w/ Breakfast Service!

ConnieRating, 5 stars8 months ago
Everything about the Hillside B&B was fabulous, especially Monica. There were eight adults and two children, and we all found our space and it never felt crowded. The setting is so beautiful. Nestled in a hillside, a beautiful pines, privacy on all sides and a spectacular view. The beds were comfortable and the linens soft and lovely. It was wonderful to be able to have breakfast together served by this delightful host. Everything was perfect.
Top Guest favourite
Home in Wisconsin Dells
5 out of 5 average rating, 26 reviews

Big Blue | Dwntown | Arcade | Basktball | Playgrnd

DaleRating, 5 stars1 week ago
Great house with tons of room and close to downtown but with privacy.
Guest favourite
Home in Wisconsin Dells
5 out of 5 average rating, 6 reviews

Birdhouse retreat on 5 acres Sauna. Theater. Games

EmilyRating, 5 stars1 month ago
This property was just how I imagined it to be. The calmness of nature surrounding the home was AMAZING! Aesthetics of the home were well thought out! LOVED the choice of kitchen appliances and cookware! Overall the host was super sweet and communicated well!
Top Guest favourite
Home in Baraboo
5 out of 5 average rating, 54 reviews

Perfect Location, Downtown Baraboo w/ Hot Tub

Sarah & DakotaRating, 5 stars5 days ago
We loved our stay at Courtney + Kevin’s place! It was immaculately clean, comfortable, and had everything we needed to have a great stay. The hot tub was nice to relax in after a long day of adventuring. Our two year old son benefitted from the kids plates, cups, and cutlery that they provide and used the second bedroom which despite being small, is big enough for a pack n play! The bed was soo comfortable with nice pillows and they provide so many amenities like washer pods, extra soap, shampoo, conditioner, body wash, and have enough pots and pans to actually cook a meal! The neighborhood was so peaceful and quiet at night! We loved being in the middle of the places we were visiting like House on the Rock and the Dells. We enjoyed the local circus museum and ate twice at Broadway Diner just because we loved it so much!
Guest favourite
Home in Baraboo
4.98 out of 5 average rating, 92 reviews

Game Room! Hot Tub! Fire Pit! Patio! Baraboo/Dells

HusnaRating, 5 stars2 weeks ago
Great location for an intimate getaway! Well stocked for everyone with lots of games and kids toys. Our family had a wonderful time and we will be sure to return. Thank you!
Guest favourite
Home in Merrimac
5 out of 5 average rating, 13 reviews

Cody’s Cabin - Lake front property, Ski & Fish

BlakeRating, 5 stars9 months ago
Awesome place, very well maintained. Beautiful views.
Top Guest favourite
Home in Baraboo
5 out of 5 average rating, 7 reviews

Gracie Manor - Modern 7 Acre Estate

HuyRating, 5 stars2 months ago
We had an amazing time staying here for a ski trip to Devils Head! The house was even nice than the pictures showed and there were so many amenities for young kids. The kitchen and bathrooms were also well stocked, all of which made the stay so comfortable!
Top Guest favourite
Home in Baraboo
5 out of 5 average rating, 62 reviews

Theater-Private Yard-Patio-Firepit-Grill-Downtown

RonaldRating, 5 stars2 months ago
We again (second timer) stayed due to a ski trip at Cascade Mountain with family. The house is amazing, we didn't even use all the amenities. Everything is awesome and suited our all our needs. The house is very clean with plenty of towels. Their welcome book lists instructions for everything about the house: TVs, Disney+, WiFi password, thermostat adjustment, etc. The house is old (1920's?), however the owners installed the modern touches that count. This has become our main stay whenever we plan an area ski trip - it feels like home. PS: We left the house clean and felt obligated since it's amazing!

Private house rentals

Guest favourite
Home in Lodi
5 out of 5 average rating, 12 reviews

Okee Bay House on Lake Wisconsin w/ Private Dock!

MichelleRating, 5 stars1 month ago
We enjoyed staying here so much! My sister and I came home see family. This house was perfect for our families to share. ( we each have two kids) Do note that the upstairs stays warm and the downstairs stays on the cooler side. They do have an extra heater available in the down stairs area. The mornings are beautiful and my daughter LOVED seeing the pelicans on the lake. We will be back. 😊
Guest favourite
Home in Portage
4.94 out of 5 average rating, 101 reviews

Wisconsin River Valley Farmhouse: Fire Pit & View

SteveRating, 5 stars2 months ago
We had a great stay at the farmhouse while skiing at Cascade Mtn. Very clean, well stocked, warm and cozy. The kids enjoyed their own place to watch movies and we all enjoyed the nice gas fireplace. Very convenient to Cascade. Beautiful sunrises! Lots of room and very comfortable- highly recommend!
Top Guest favourite
Home in Portage
5 out of 5 average rating, 21 reviews

Whole House 15 min to WI Dells

SaraRating, 5 stars9 months ago
Kristen was a great host. Responsive within the hour after reaching out. She recommended local locations for our bachelorette party to go to, as well as a quick and easy back way to the downtown dells. She arrived as we checked in to show up how to use the fire pit and explain where certain things were. She met the girls for check out and did a quick inspection to make sure all was ready for us to head out. The house was perfect for 16 girls and had enough bathrooms for everyone to get ready with no arguing! lol. The back yard patio was PERFECT for our Saturday and has the cutest little tiki bar for that beachy ambiance. The location is quiet and peaceful and we felt right at home. Many of us were stating how we would gladly stay here again with our families. Thanks Kristen!
Top Guest favourite
Home in Wisconsin Dells
4.92 out of 5 average rating, 76 reviews

Cottage home right off the Wisconsin Dells strip!

MelissaRating, 5 stars8 months ago
Great place to stay! Super close to the strip, but quiet! Very quaint with wonderful amenities! Awesome beds! Great tv’s! Wonderful yard with a fire pit! The hosts go above & beyond! We will stay here anytime we are in the area in the future! HIGHLY RECOMMEND.
Guest favourite
Home in Lake Wisconsin
4.86 out of 5 average rating, 14 reviews

Lake Landing

ConnorRating, 5 stars2 weeks ago
Such a great stay! We loved the big living room and kitchen, plus the bedrooms with attached bathrooms was a good addition. It was a great location to spend time with family, and right next to Lake Wisconsin! We would happily stay again!
Top Guest favourite
Home in Portage
4.97 out of 5 average rating, 31 reviews

House on the River near WI Ski Resorts

JustinRating, 5 stars2 months ago
Awesome stay right by the river for a ski trip with friends. Great place with nice design and plenty of room for everyone. Would stay again!
Top Guest favourite
Home in Baraboo
5 out of 5 average rating, 80 reviews

Hawsin Haven

TimRating, 5 stars1 week ago
Jenn and Amber have literally thought of everything. Attention to detail only begins to describe their home from the decorating to the amenities and comfort of beds and fully stocked kitchen with pans and utensils. The house was immaculate and their detailed instructions for how everything works were greatly appreciated. We would look no further than Hawsin Haven when we are back in the Baraboo area. Great value for what you get in this upscale house and setting.
Superhost
Home in Baraboo
4.9 out of 5 average rating, 10 reviews

4 min to Devils Lake State Park/ sleeps 11

SandyRating, 5 stars6 months ago
We had 6 adults and 1 one dog staying with us and felt comfortable. The kitchen had everything we needed, enough room for cooking and eating. Great to have a fenced yard for the dog. Loved the huge sectionals, everyone was able to find a seat and get comfy!

Destinations to explore