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
5.0 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!

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
5.0 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.

Guest favourite
Home in East Troy
4.94 out of 5 average rating, 115 reviews

Lakefront House on Potter Lake

Welcome to Potter Lake Retreat, brand new home on beautiful Potter Lake with stunning views from all rooms. Enjoy swimming, fishing, boating, kayaking, a paddle board and fire pit available for your use during your stay. Bring your boat and dock at our attached private pier. We have (3) single seat kayaks available for your use. You will have access to the top and main floors. The basement is not accessible. Contact us for details! Potter Lake is a quiet lake.

Top Guest favourite
Home in Cudahy
5.0 out of 5 average rating, 57 reviews

Lake Michigan Views • Private Cedar Sauna

Private cedar barrel sauna, cozy fireplace, and peaceful outdoor spaces just steps from Lake Michigan. Unwind beneath the string lights in the seasonal Garden Lounge, gather around the chiminea, or stroll scenic bluff trails along the lake. Just minutes from downtown Milwaukee, beaches, breweries, restaurants, museums, festivals, and sporting events, this thoughtfully designed getaway is the perfect home base to relax, recharge, and explore year-round

Top Guest favourite
Dome in Caledonia
5.0 out of 5 average rating, 106 reviews

Indigo Zen Garden | Private Dome Escape

Escape to a romantic glamping retreat centered around a cozy stargazing Dome and a beautifully furnished bedroom tent. Soft ambient lighting sets a peaceful, intimate mood, while the gazebo with a fire table and the fire pit invite long evenings under the stars. A separate kids’ play tent is available for families. Elevate your stay with an optional outdoor movie night and popcorn under the stars.

Top Guest favourite
A charming outdoor seating area is featured, with two wicker chairs and a small table adorned with vibrant flowers. A large green umbrella provides shade over the space, while decorative elements add character to the inviting layout.
Apartment in South Milwaukee
5.0 out of 5 average rating, 78 reviews

Music themed couples getaway hot tub walking paths

Enjoy the cozy fire while relaxing in the hot tub in the private coved patio. Artistic "gallery like" lower apartment is nestled in a beautiful wooded neighborhood just 15 mins from Milwaukee's Downtown. Near by scenic views of the MKE skyline, Hoan Bridge, Summerfest Grounds and steps away from Lake Michigan, golf course and Seven Bridges hiking attraction.

Popular amenities for Caledonia holiday rentals