Holiday rentals in Caledonia

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Top-rated holiday rentals in Caledonia

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost
The living area features a blue couch complemented by a yellow armchair, arranged around a coffee table. A rug with a modern pattern covers the floor, adding warmth. Wall art and plants contribute to the inviting ambiance, while dimmable lights enhance the space.
Apartment in Kenosha
4.9 out of 5 average rating, 276 reviews

Spacious 2-BDRM/ Safe area Great for work & vacay

You will enjoy this carefully designed, well-decorated and well-furnished basement apartment. It is roomy (over 950 feet), pleasant, private and quiet in a residential area. Whether you ( 1-4 guests) come for work, business, family or a special function, its full kitchen, classy bathroom, extra-comfortable king and queen size beds, blender, high-speed internet and ergonomic chairs (2nd on demand) as well as free parking will add comfort and extra ease to your stay, and make it one to remember.

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
4.92 out of 5 average rating, 271 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, 15 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 wooden deck features a partially covered jacuzzi, emitting steam amid a rainy backdrop. A stone fire pit, with a glowing flame, stands nearby, providing warmth. A patio set, including a chair, complements the serene outdoor setting surrounded by greenery and trees.
Guest suite in Racine
4.91 out of 5 average rating, 292 reviews

Racine theme Airbnb at the Red Birch on Erie

Home is set in a quiet neighborhood with a working vegetable farm for a backyard where deer, squirrels, geese and birds entertain. You will enjoy unobstructed, amazing sunsets along with Racine themed artwork and memorabilia, all retro and eclectic in design. It's a short drive to the Lake Michigan shoreline and just minutes away from downtown and the finest beaches! You're host has props from his Old Times photo studio that are available for photography on the grounds in special settings.

Superhost
Place to stay in Racine
4.85 out of 5 average rating, 806 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, 112 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.

Top guest favourite
Home in Milwaukee
5 out of 5 average rating, 12 reviews

Bright & Quiet 2BR | Parking | Airport & Bay View

Every room is thoughtfully renovated with a nod to 70s-inspired design. New kitchen, refreshed bathroom, freshly painted bedrooms, and a redesigned living room. No detail was overlooked. Curl up with a book on the sofa, put on a movie, or enjoy a quiet evening in a space that’s cozy, stylish, quiet and completely your own. Whether you’re passing through or staying a few days — we’ve got you covered. Fast WiFi, driveway parking, and just a 5 minute drive to the airport and Bay View.

Top guest favourite
Guest suite in South Milwaukee
4.99 out of 5 average rating, 92 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.

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.
Guest house in Racine
4.9 out of 5 average rating, 254 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.

Superhost
A wooden dining table is surrounded by six matching spindle-back chairs. A light-colored table runner runs across the center, complemented by a simple candle holder. Sunlight pours in from a nearby window, illuminating the warm wood floors and creating a cozy dining space.
Home in Caledonia
4.71 out of 5 average rating, 28 reviews

Convenient Countryside Oasis

Escape to the serene countryside with our charming abode, offering a tranquil retreat from the hustle and bustle of city life. Just a stones throw away from downtown, this cozy 3 bedroom home boasts beautiful wood floors, creating a warm and inviting ambiance for your stay. Despite its secluded setting, our rental is conveniently located just a short distance from downtown Milwaukee, offering easy access to a myriad of attractions and entertainment options.

Top guest favourite
A cozy sunroom is featured with large windows, allowing natural light to fill the space. A comfortable gray sectional sofa provides seating, accompanied by a decorative pillow. Soft lighting fixtures and a unique chandelier add a welcoming touch to the inviting atmosphere.
Home in Kenosha
4.99 out of 5 average rating, 132 reviews

6th Ave Harborside

Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. One night stays are available on a limited basis - reach out for details!

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, 140 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

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