Holiday houses in Caledonia

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Top-rated holiday rentals in Caledonia

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Guest favourite
A rustic interior showcases handcrafted stonework paired with warm wooden accents. Natural light highlights the cozy organization of the space, featuring a fireplace in the foreground and a ladder leading to an upper level, while a glimpse of the adjoining room is visible in the background.
Home in Racine
4.91 out of 5 average rating, 275 reviews

“Rustic Farmhouse Retreat” at a working farm

A charming little farmhouse filled with antiques & eclectic artwork from all over the world. It is situated in the middle of a working farm that raises a plethora of exotic fruits, vegetables, shiitake mushrooms, and flowers for local gourmet restaurants. The house interior has a unique design decorated with beautiful hand crafted stonework accented with exotic driftwood trim from old wooden shipwrecks. Try our outdoor Neapolitan wood fired oven for the best pizza ever. A truly unique getaway!

Top Guest favourite
Home in Caledonia
5 out of 5 average rating, 21 reviews

Family fun entertainment with cinematic experience

Welcome to the Prairie Getaway-your ultimate family basecamp, just 5 mins from I-94. Fun is the mission with our fully furnished basement: the 86 inch home theater, surround sound system, pinball and arcade machines make it ideal for movie & game night! 🕹 Adjacent to a tranquil park and prairie paths, this home blends comfort and convenience, promising a memorable time for all ages. Enjoy the perfect blend of suburban peace with Milwaukee and Racine nearby. Escape the city without going far!

Top Guest favourite
A well-maintained trailer is surrounded by green shrubs and decorative stones. A wooden picnic table is placed on a stone patio, providing a space for outdoor dining. The sky is partly cloudy, contributing to the tranquil atmosphere of the outdoor setting.
Campervan/RV in Franklin
5 out of 5 average rating, 16 reviews

The Crows Nest Camper

Enjoy the lovely setting of this romantic spot in nature. you have a private pond with a little Trail to walk through still close to the city and feel so far away in nature.Perfect for relaxation or active fun! Just 5 minutes away is The Rock Sports Complex, offering top-tier activities like Topgolf, minor league baseball, an umbrella bar, hiking trails, and more. Whether you’re seeking tranquility or adventure, our cottage provides the ideal getaway for both.BOAT TOUR AVAILABLE to 11people

Superhost
Place to stay in Racine
4.84 out of 5 average rating, 817 reviews

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

Top Guest favourite
An outdoor patio is shown with a red umbrella providing shade over a black table and four metal chairs. A barbecue grill is positioned nearby, with a view of a green lawn and a distant red barn visible in the background.
Home in Racine
4.98 out of 5 average rating, 115 reviews

Farm House Retreat w/ Private Backyard & Garage

Comfort, convenience and country views await you! Relax on the private patio and soak up the beautiful scenery. Minutes from the lakefront, Racine Zoo and short drive to Milwaukee, you'll enjoy this completely updated home. Cook a meal in the fully stocked kitchen and kick back in the comfy family room. Whether you are here to visit family, attend special events or business travel, you'll find everything you need here. And if you're a little country at heart, the view will not disappoint.

Guest favourite
A cozy living space features a floral-patterned couch accompanied by a wooden coffee table. The walls are adorned with warm wood paneling, complemented by soft lighting from a wall sconce. Greenery is present with potted plants, adding a touch of nature to the space.
Home in Oak Creek
4.87 out of 5 average rating, 112 reviews

Spacious Ranch Home Oak Creek close to Airport

Chalet style ranch home is fully furnished and offers 2400 square feet of private usable space. The 3 bedrooms, living room, dining room, family room, 1 1/2 bathrooms, kitchen, and kitchen table area are all located on one floor. You will love waking up in the morning in this quiet suburban neighborhood and looking out the many windows at the park across the street. Close to the heart of Oak Creek Drexel Town Square, 4.6 miles from the airport, & 15 minutes from Downtown Milwaukee.

Superhost
Home in Kenosha
5 out of 5 average rating, 3 reviews

Kenosha Hideaway

Welcome to Kenosha Hideaway, a charming and comfortable retreat nestled in the heart of Kenosha! Ideally located, you're just minutes from downtown, local colleges, dining, and the beautiful Lake Michigan shoreline. This inviting hideaway is perfect for relaxing escapes or exciting adventures. Whether you're visiting family, exploring the city's vibrant attractions, or enjoying a peaceful retreat, Kenosha Hideaway offers the comfort, convenience, and charm for a memorable stay.

Top Guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 100 reviews

Historic Hawthorne House

Nestled just steps from Grant Park Beach & Lake Michigan, the scenic Seven Bridges Trail, and the lush Grant Park Golf Course, this unique rental offers a blend of history, charm and comfort. Only a 10 minute drive to Mitchell International Airport and an easy 20 min drive to downtown Milwaukee. Whether you're here to unwind in nature, explore the local parks, enjoy a peaceful lakeside stay, or enjoy the best that Milwaukee has to offer this home has everything you need.

Top Guest favourite
A rustic cabin with dark wooden logs is situated among tall green trees. The spacious porch features a railing and several chairs, inviting relaxation. Sunlight casts warm tones across the facade, while the surrounding grass and woods enhance the cabin's natural setting.
Guesthouse in Racine
4.9 out of 5 average rating, 259 reviews

Charming log cabin in the woods

This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

Top Guest favourite
An open living area showcases a sleek gas fireplace with a mounted television above. Comfortable seating includes leather armchairs and a cozy couch. Large windows and French doors provide access to a porch and offer scenic views of the lake.
Home in Racine
4.99 out of 5 average rating, 123 reviews

Beautiful home with amazing Lake Michigan views

Historic home with modern upgrades that has gorgeous views of Lake Michigan. The home was recently upgraded with amazing features including two gas fireplaces, high end kitchen finishes, and a spa style primary bathroom with heated floors. The house is located in the Southside Historic District, steps from the lake, and a short walk to downtown Racine. You can enjoy the local restaurants and shopping, explore the lakefront, or stay in and relax in the peaceful home.

Guest favourite
The living area features warm wooden walls and a rustic charm. Natural light filters through large windows and skylights, illuminating a cozy seating arrangement. A small wood stove stands near a patterned area rug, while musical instruments are positioned around the space, enhancing its inviting atmosphere.
Cabin in Hubertus
4.94 out of 5 average rating, 587 reviews

Hugel Hutte - Log Cabin Getaway

Welcome to the Hugel Hutte! This cute little cabin is perched on the hill top. It's feels like a tree house! You have the kitchen to use, but the famous Fox & Hound's restaurant is just steps away. It's literally right next door. So grab a few drinks and dinner...and walk home to your cabin retreat for the night. Enjoy the tranquil naturescape surrounding the house.

Top Guest favourite
A welcoming entrance to Spring Willow Farm is showcased, featuring a sign amidst vibrant red, yellow, and purple tulips. Lush trees and a white fence frame the pathway, leading to the farm's main building in the distance.
Guest suite in Union Grove
4.97 out of 5 average rating, 146 reviews

Peaceful Horse Farm Retreat

Reconnect with nature at this unforgettable escape to a 54 acre horse farm. Get away and relax while enjoying the peaceful rhythm of Spring Willow Farm. Write, paint, be creative, do yoga, take walks, fly a kite, pet a horse, enjoy the outdoor firepit, or simply do nothing.

Popular amenities for Caledonia holiday rentals