Vacation rentals in Caledonia

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Top-rated vacation rentals in Caledonia

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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

4.96 out of 5 average rating, 238 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 favorite

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, 128 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.

Top guest favorite

The house is illuminated at night, revealing a spacious deck adorned with soft lighting. Large windows display a welcoming interior ambiance. The surrounding garden features lush greenery and blooming flowers, while the towering trees create a serene backdrop.

Home in Baraboo

5 out of 5 average rating, 145 reviews

Crown Lodge, Baraboo Bluffs

Nestled deep in the Baraboo Bluffs on a dead-end country road. A true cabin-in-the-woods feel without sacrificing space or amenities. Perfect for family getaways, outdoor enthusiasts, or anyone craving a peaceful recharge. Whether you’re sipping coffee or drinks on the deck while watching wildlife, hiking the bluffs, skiing nearby or visiting the Dells, there’s no shortage of things to do, or not do! Minutes from Devil’s Lake, Devil’s Head Resort, Ice Age Trails & 25 minutes to Wisconsin Dells

Guest favorite

A two-story home with a mix of stone and wood siding sits on a grassy lot. Large windows allow natural light inside. A paved driveway leads to the garage, with trees and a view of open land in the background.

Guest suite in Sun Prairie

4.89 out of 5 average rating, 369 reviews

Entire Lower Level, Countryside Garden Suite

Welcome to our home! We have upgraded our Garden (lower) Level to host travelers much like ourselves and long-term guests. The view of our backyard is incredible! You will find yourself lost in the country, yet less than ten minutes from all the excitement that Madison has to offer. Along with a private drive and entrance, you will have 1,000 square feet of comfort all to yourselves. This property is perfect for a quiet getaway we all need from time to time. All designed with you in mind.

Guest favorite

The exterior of a recently remodeled lake house showcases a modern green facade and wooden front steps leading to a welcoming porch. A large window offers glimpses of the lake, while a grassy area and utility pole are present in the foreground.

Home in Briggsville

4.93 out of 5 average rating, 182 reviews

The Lake House on beautiful Mason Lake

"The Lake House" is located on beautiful Mason Lake in Briggsville, WI. Our home is a freshly remodeled 2 bedroom, 1 bathroom lake house with 36 ft. of lake frontage. The property has a huge fenced in back yard, concrete patio and a new pier (2021) for outside fun. We can accommodate two vehicles on the black top driveway, public street parking and a large public parking lot for boat / rec. trailers right across the street. The property is also located on a ATV/UTV and snowmobile trail system.

Top guest favorite

Cabin in Adams

4.94 out of 5 average rating, 448 reviews

Cozy Log Cabin in the Woods

Adams County TRH License #7333 Welcome to the Lucky Dog Cabin! Nestled in the trees, our charming log cabin is located 25 minutes North of the Wisconsin Dells and less than 10 minutes from Castle Rock Lake, Wisconsin River, and Quincy Bluff State Park. Come relax, unplug, and get away from it all. Enjoy the fresh air, starry nights, and peaceful nature sounds. Our 9 acre property offers a beautiful trail that leads to gorgeous sunset views, through the forest. A true nature-lover's paradise!

Guest favorite

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

4.92 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.

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

4.95 out of 5 average rating, 113 reviews

Grandma's House: Coming Soon-Fall Colors!

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.

Superhost

A serene lakeside view is captured, featuring calm waters reflecting the sky and surrounding greenery. A sandy beach is visible in the foreground, complemented by a large tree providing shade. Soft clouds drift across the blue sky, enhancing the tranquil atmosphere.

Guesthouse in Poynette

4.9 out of 5 average rating, 254 reviews

Simple Cabin*Lake View rustic cabin in rural WI

The Simple Cabin on Lake Wisconsin is a simple and clean space. It would be ideal for an individual or couple who are enjoying the beautiful outdoors by day, and would like a bed by night. It is 350 sq ft for the entire cabin consisting of bedroom, small full bathroom, and living area. You will enjoy 180 degrees of across-the-water views. 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) & Mirror Lake.

Guest favorite

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, 170 reviews

Relaxing Cottage near Devils Lake Baraboo WI Dells

Welcome to our charming two-bedroom cottage, perfect for relaxation and 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!

Guest favorite

A charming cabin structure is illuminated at night, showcasing its mid-century architectural style. The building features large, glowing windows that highlight the warmth inside, surrounded by lush greenery and gently lit pathways leading to a peaceful outdoor setting.

Cabin in Merrimac

4.91 out of 5 average rating, 203 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 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

4.98 out of 5 average rating, 351 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