
House holiday rentals in Caledonia
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Top-rated house rentals in Caledonia
Guests agree: These houses are highly rated for location, cleanliness and more.

“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!
4.91 out of 5 average rating, 277 reviews
The July House: Steps From the Lake
You’re invited to come enjoy amazing lake views from this adorable 1920s house! Our family used to live here, and we loved it way too much to sell it. The whole space has since been re-imagined for guests, including two full newly-renovated modern baths. Some interesting original features still remain, such as exposed Cream City brick and a wood burning fireplace. Lake view from living/sitting room and all bedrooms, within walking distance to historic downtown's awesome restaurants and shops.
4.87 out of 5 average rating, 485 reviews
Bright, Airy, Backyard by Carthage, UWP, Microsoft
Newer, modern 4BR/2.5BA home in peaceful residential neighborhood. 10min from beautiful Kenosha beaches, Microsoft, UWP, Carthage, harbor market, museums, restaurants, & more! The house features 2 dining areas, dedicated office space, and a large unfenced backyard with relaxing patio seating. Very family friendly! Perfect for your family vacation, friends getaway or business trip -we are experienced hosts. Book with confidence! 30min to Milwaukee airport, 50min to O’Hare, 25min to Six Flags
4.98 out of 5 average rating, 152 reviews
The Farmer's Retreat
Enjoy a stay in this cozy home that boasts the perfect balance of city and country. Many conveniences all within 10 minutes include Starbucks, Walmart, Grocery, dining and shopping. The home itself is nicely updated with a full kitchen, dining room and a large living area. Not to be left out is my favorite feature - The Spacious backyard and outdoor patio. This is a great place to run and play or just enjoy some fresh air. Great stay for whatever brings you to the Kenosha/Racine area
4.91 out of 5 average rating, 109 reviews
Stunning Home Across The Street From North Beach
Newly remodeled home on Michigan Blvd. We went the extra mile in creating this beautifully curated, lush, and stylish home! Kick back and relax in one of the many thoughtfully designed rooms and the huge front outdoor deck with amazing views of Lake Michigan! Anywhere you gaze, you will find a visually stimulating experience in this home! Across the street from Lake Michigan, North Beach, and Kids Cove Playground. Short walk to Racine Zoo, the Marina, downtown Racine shops and restaurants.
4.96 out of 5 average rating, 137 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.
4.98 out of 5 average rating, 118 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.
4.87 out of 5 average rating, 112 reviews
Fabulous Walkers Point Mansion w/ Bar andFireplace
This stunning Walker's Point historic mansion is completely re-imagined with interior spaces that will delight you and your guests. Host a memorable get together with friends or family and relax by the bioethanol fireplace, enjoy everything the vibrant neighborhood has to offer. We have some beautiful spaces for your enjoyment, including a finished-attic hangout space, and a secret vintage-inspired lounge in the basement. Enjoy plenty of Milwaukee history in a spectacular new form!
5.0 out of 5 average rating, 170 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.
4.99 out of 5 average rating, 124 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!
4.99 out of 5 average rating, 139 reviews
Family friendly, Private Patio, Walkable, Quiet
Cute and bright home central to everything Milwaukee has to offer. Located in sought after quiet community due to its proximity to all main attractions while providing safety and peace for residents and visitors. Our property is less than 10mins from heart of Milwaukee, walking distance to main attractions such as Brewers stadium and state fair. We do our absolute best to be exceptional hosts so hope you decide to stay with us.
4.9 out of 5 average rating, 105 reviews
Historic Racine Property! - The Parish House
Stay in a little piece of history in Racine, WI! Built at the end of the 1800’s for George Murray and his family, this portion of the Murray Mansion functioned as the servant’s quarters for the family home. Minutes away from downtown Racine and some of the most stunning beaches on Lake Michigan, this renovated historic home is the perfect escape for your stay in Wisconsin.
4.94 out of 5 average rating, 234 reviewsPopular amenities for Caledonia house rentals
House rentals with a pool

Rosie’s Eastside Garden Bungalow
4.97 out of 5 average rating, 122 reviews
Brewers Hill Gem w/hot tub & seasonal shared pool
4.92 out of 5 average rating, 197 reviews
Close to Lake with Great Ammenities & Breakfast!
4.77 out of 5 average rating, 168 reviews
Home away from Home
4.93 out of 5 average rating, 172 reviews
7 1/2 Acre Private Estate w/inground pool, hot tub
4.85 out of 5 average rating, 82 reviews
Private Pool and Hot Tub! Private Backyard Oasis!
4.94 out of 5 average rating, 51 reviews
Paradiso Vacation
5.0 out of 5 average rating, 59 reviews
Kalo House | Mid-Century Modern Retreat
5.0 out of 5 average rating, 18 reviewsWeekly house rentals

TheGlassCabin @ HackmatackRetreat
4.96 out of 5 average rating, 241 reviews
Brew City Inn with Hot Tub | Summerfest House
4.95 out of 5 average rating, 114 reviews
Estate on 1 Acre. Fall getaway w/Hot Tub-Sleeps 16
4.92 out of 5 average rating, 306 reviews
Historic on The Avenue
4.96 out of 5 average rating, 165 reviews
Cream City Victorian | Parking | AC | Patio | Walk
4.97 out of 5 average rating, 167 reviews
Center Lake View Cottage, near Camp&Silver Lakes
4.94 out of 5 average rating, 131 reviews
Family fun entertainment with cinematic experience
5.0 out of 5 average rating, 24 reviews
Lake Michigan Romantic Getaway
4.72 out of 5 average rating, 39 reviewsPrivate house rentals

Lake Michigan Views • Private Cedar Sauna
5.0 out of 5 average rating, 60 reviews
The Gatsby! Pro Cleaned, Self Check In Sleeps 12
4.92 out of 5 average rating, 39 reviews
Gorgeous Historical Mansion on Lake Michigan
5.0 out of 5 average rating, 33 reviews
Cozy Mid-century Ranch
4.97 out of 5 average rating, 36 reviews
The Rawson House
4.98 out of 5 average rating, 62 reviews
Cozy historic Cream City Brick Workers Cottage
4.89 out of 5 average rating, 94 reviews
Waterfront w/Lake Views, walk to the beach!
4.99 out of 5 average rating, 80 reviews
4 bedroom | 3 bath | Pet friendly with amenities
5.0 out of 5 average rating, 38 reviewsDestinations to explore
- Chicago Holiday rentals
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- Naval Station Great Lakes
- Six Flags Great America
- Alpine Valley Resort
- Wilmot Mountain Ski Resort
- Baird Center
- Illinois Beach State Park
- American Family Field
- Milwaukee County Zoo
- Milwaukee Public Museum
- Marquette University
- Riverside Theater
- Bradford Beach
- Fiserv Forum
- Pabst Mansion
- Wisconsin State Fair Park
- Holy Hill National Shrine of Mary
- Lake Geneva Public Library
- Gurnee Mills
- South Shore Park
- Mitchell Park Horticultural Conservatory
- Discovery World
- Betty Brinn Children's Museum
- Atwater Park
- Lake Geneva Cruise Line





