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Vacation rentals in Caledonia

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Top-rated vacation rentals in Caledonia

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

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Home in Racine

4.91 out of 5 average rating, 242 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!

Condo in Kenosha

4.92 out of 5 average rating, 207 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

Guest suite in Racine

4.9 out of 5 average rating, 252 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.

Townhouse in Bay View

4.95 out of 5 average rating, 388 reviews

Vintage Bay View - Big Backyard, Big 1 Bedroom

Welcome to your Milwaukee getaway! Located in the Bay View area, you're walking distance from the best farm-to-table restaurants, music venues, art fairs, and craft beer in the city. Not only that, but Lake Michigan's beaches, Miller Park, and downtown are a short drive away. The location is ideal. The place was created with a 70's midwestern feel, with wood-paneled furniture pieces and mod design. It also boasts a giant kitchen and backyard with grill. We can't wait for you to visit!

Villa in Racine

4.96 out of 5 average rating, 114 reviews

Gorgeous historical mansion on Lake Michigan

Welcome to the historic Carpenter House! This is an opportunity to stay in a former Bed & Breakfast overlooking Lake Michigan. A historical neo-classical home built in 1896 with tons on history. The home was completely renovated a few years ago. Wake up and sit on the front porch and enjoy the beautiful view of Lake Michigan. The house is located in the historical district in Racine. The home boasts a ballroom on the 3rd floor that is suitable for small events and a private cute garden.

Guest suite in Cudahy

4.92 out of 5 average rating, 103 reviews

RARE Private Butler’s Suite in Historic Home

Luxurious, Industrial, historical. Sherlock Holmes meets Restoration Hardware. Declared a historical landmark, the home was built in 1892 and owned by the architect who designed the township of Cudahy. It is one of the last remaining remnants of the era. The room itself was a former speakeasy during prohibition. 10 minutes from the airport. 12 minutes from downtown Milwaukee. A short walk to Lake Michigan and Sheridan Park. Plenty of coffee shops and restaurants around.

Guesthouse in Racine

4.9 out of 5 average rating, 214 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.

Home in Kenosha

4.96 out of 5 average rating, 216 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Home in Racine

4.94 out of 5 average rating, 154 reviews

Root River Home - Waterfront property - Sleeps 8+

Beautiful waterfront escape awaits you. Located along the Root River, Village of Caledonia, WI (Racine County) 10 Minutes / 3 Miles from North Beach (Lake Michigan) and only 5 minutes from Quarry Lake Park (Swimming and Recreation Area). Includes Kayaks, Canoes, Row Boat, Paddle boat, Firewood, Gas Grills, Netflix, WIFI, TV, and Wi and Playstation for the Kids, Ping Pong Table, outdoor firepits and much much more.

Rental unit in Kenosha

4.99 out of 5 average rating, 148 reviews

Downtown-Treetop Deck-2Bd/2Bth

This one-of-a-kind, shabby-chic second floor apartment is in the heart of Downtown Kenosha, walking distance to coffee shops, restaurants, museums, and Lake Michigan beaches. Enjoy the large, completely secluded back deck equipped to grill, dine, and relax tucked amongst neighborhood buildings with a tree top view. The apartment is great for a romantic rendezvous, a girlfriend getaway, or for an extended stay.

Condo in Racine

4.97 out of 5 average rating, 240 reviews

Gorgeous renovated 1200sf apt with lake views

Beautiful completely renovated and modernized 1,200 sq. ft 1 bedroom apartment on the upper floor of an old Main Street commercial building from the late 1800s in Racine. In addition to all the modern amenities inside the apartment, you'll enjoy using the "attached" public parking garage ($3.50), which allows you to enter a few short steps from where you park - without climbing any stairs at all.

Cabin in Kenosha

4.81 out of 5 average rating, 605 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Two decks overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Vacation rentals for every style

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Popular amenities for Caledonia vacation rentals

Free parking on premises

Air conditioning

Stay near Caledonia's top sights

Racine Zoo45 locals recommend

Wind Point Lighthouse25 locals recommend

River Bend Nature Center20 locals recommend

Oh Dennis! Saloon & Charcoal House9 locals recommend

Shoop Park Golf Course8 locals recommend

DeRangos Pizza Palace8 locals recommend

Other great vacation rentals in Caledonia

Home in Racine

5 out of 5 average rating, 16 reviews

2 King Beds, EV charger, Near Lake Michigan

Guest suite in Kenosha

4.95 out of 5 average rating, 92 reviews

Kenosha - enjoy great food and Lake Michigan

Condo in Racine

4.94 out of 5 average rating, 66 reviews

Artist loft in Racine

Rental unit in South Milwaukee

5 out of 5 average rating, 36 reviews

Cozy private getaway, Hot Tub, Music theme

Home in Oak Creek

4.85 out of 5 average rating, 71 reviews

Spacious Ranch Home Oak Creek close to Airport

Home in Racine

4.97 out of 5 average rating, 65 reviews

Farm House Retreat w/ Private Backyard & Garage

Cabin in Racine

4.98 out of 5 average rating, 49 reviews

Rustic Riverside A-Frame Retreat: Secluded Charm.

Guest suite in Brookfield

5 out of 5 average rating, 209 reviews

In the Canopy (beautiful Brookfield/Milwaukee)

Quick stats about vacation rentals in Caledonia

Total rentals
40 properties
Nightly prices starting at
$30 before taxes and fees
Total number of reviews
2.4K reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Caledonia?
Yes! Work meets play with ease at over 20 vacation rentals in Caledonia featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Caledonia have wifi?
Absolutely! We offer over 20 house rentals with wifi in Caledonia. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Caledonia have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Caledonia. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Caledonia have free parking?
Absolutely! We offer over 20 house rentals with free parking in Caledonia. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Caledonia have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Caledonia. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Caledonia?
Four-legged friends are welcome in Caledonia. Choose from more than 10 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Caledonia?
Experience the best of Caledonia with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Caledonia?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wifi, over 20 homes with free parking, over 20 homes with a kitchen, over 20 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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