Holiday rentals in Caledonia

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Top-rated holiday rentals in Caledonia

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Top guest favourite
The dome structure glimmers in the moonlight, surrounded by tall trees that create a serene ambiance. A warm glow from a nearby fire pit reflects off the dome's surface, enhancing its unique design. The wooden platform adds a cozy touch to the natural setting.
Dome in Wisconsin Dells
4.97 out of 5 average rating, 167 reviews

Dells Domes - Riverview Escape - Glamping Dome 4

Staying in a dome amidst nature is a unique experience. The circular structure offers an amazing view of the surroundings, with peaceful sounds of rustling leaves, chirping birds, and a flowing river below. The cozy dome has a queen size bed, night stands, a seating area, mini fridge, and a k-cup coffee maker & heater/ac. At night, the starry sky and nature's sounds lull you to sleep. Waking up, you feel refreshed, and the peaceful surroundings and breathtaking views leave a lasting impression.

Top guest favourite
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
4.96 out of 5 average rating, 248 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
A quaint gray house features a dark front door framed by two windows with flower boxes. A stone path leads to the entrance, surrounded by lush green grass and shrubs. The home's simple design is complemented by a picturesque backdrop of leafy trees.
Home in Baraboo
4.96 out of 5 average rating, 142 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.

Superhost
Flat in Portage
4.89 out of 5 average rating, 170 reviews

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.

Top guest favourite
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
4.95 out of 5 average rating, 112 reviews

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.

Top guest favourite
The exterior of the barn features a sleek black facade with white trim, including multiple windows that allow natural light to enter. A wooden fence provides privacy, and the entrance is marked by a simple white door. Lush greenery surrounds the barn, enhancing its rustic charm.
Cabin in Princeton
4.99 out of 5 average rating, 126 reviews

Private Riverfront, Converted Barn *EV Charger*

Fox River Barn is located in a picturesque setting with stunning views of the Fox River in Princeton, WI. This 1940s barn has been lovingly converted into a comfortable living space with modern features and amenities, making it the perfect retreat for a romantic getaway or a peaceful escape from the city. Inside, the bones of the barn are present. From beams and rafters on the main level to the tall, gable barn ceiling. Just imagine all the different ways the barn had been used over time.

Guest favourite
A serene lakeside view captures a vibrant sunset, with hues of orange and blue reflecting on the calm water. Clouds scatter across the sky, complementing the tranquil scene where the water mirrors the colorful sky, suggesting a peaceful natural environment.
Cottage in Poynette
4.86 out of 5 average rating, 108 reviews

Riverbluff Cottage *near WI's best hiking& Cascade

This cottage is located in a beautiful rural setting. Set back off the main street on a private dead-end gravel drive. It's quiet and dark. 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, wineries, and agri-tourism. This cabin is part of a duplex.

Guest favourite
A hot tub is shown in the foreground, its water illuminated in soft light. Behind, a cottage is visible with large windows revealing a warm, inviting glow. The exterior is adorned with twinkling lights that enhance the cozy atmosphere of the setting.
Home in Poynette
4.9 out of 5 average rating, 210 reviews

Island View Hideaway-Hot Tub, Near 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.

Guest favourite
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
4.95 out of 5 average rating, 120 reviews

Grandma's House: Let's go Skiing!

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.

Top guest favourite
Cabin in Merrimac
4.92 out of 5 average rating, 243 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
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
4.98 out of 5 average rating, 132 reviews

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.

Top guest favourite
The exterior of a green cottage is surrounded by trees, featuring a welcoming front porch with a swing. A small bistro table and two red chairs are visible, complemented by natural landscaping of gravel and stones.
Cottage in Baraboo
4.96 out of 5 average rating, 180 reviews

Cottage near Devils Lake Baraboo

Welcome to our charming two-bedroom cottage, perfect for rejuvenation! It features a queen-sized and a full-sized bed, ideal for a small family or couple. Enjoy the double jetted tub or the luxury shower. A fully equipped kitchen, satellite TV, DVD player, and air-conditioning ensure comfort. Warm up by the Vermont wood-burning stove from November to April. Enjoy the pond view, Baraboo bluff, and meet our friendly horses and dogs. We look forward to welcoming you!

Popular amenities for Caledonia holiday rentals

  1. Airbnb
  2. United States
  3. Wisconsin
  4. Columbia County
  5. Caledonia