Caledonia Holiday Rentals

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Holiday Rentals in Caledonia

Holiday Home in Caledonia

9.8 out of 10, Exceptional, (213)
"I want to move in. We had 13 guys for a bachelor retreat and this place was perfect. Plenty of room for us all and plenty to do. We expected to spend plenty of time exploring Milwaukee, but found ourselves hanging out at the pool or fishing in the pond when we weren’t relaxing in the game room. 10/10 would recommend!"
United States
Caleb B.
The price is NZ$1,122
includes taxes & fees
21 Dec - 22 Dec
7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!

Aparthotel in Downtown Milwaukee

3.0 star property
8.8 out of 10, Excellent, (1153)
"Loved this hotel! Clean friendly and cute!!"
United States
Sharon H
The price is NZ$294
includes taxes & fees
4 Jan - 5 Jan 2026
The Plaza Hotel

Aparthotel in Westown

4.0 star property
9.0 out of 10, Wonderful, (118)
"Hosts get 5 stars for excellent communication. They checked in with me multiple times on my day of arrival to make sure everything was good and they gave very thorough instructions."
United States
Melissa
Kasa Westown Milwaukee

Apartment in Westown

4.0 star property
8.8 out of 10, Excellent, (10)
"Loved the uniqueness, location and cleanliness of the unit."
United States
Teresa
The price is NZ$285
includes taxes & fees
10 Dec - 11 Dec
ROVE LIVING/KL - Malt House

Holiday Home in New Berlin

8.4 out of 10, Very good, (8)
"We had an excellent family vacation at The Garden of Eden!!"
United States
Cheryl S.
The price is NZ$3,653
includes taxes & fees
17 Dec - 18 Dec
17-acre private Oasis estate with indoor pool, hot tub, private lake, sleeps 18

Holiday Home in Kenosha

10.0 out of 10, Exceptional, (249)
"Great weekend, thank you for the space!"
United States
Ed C.
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft

Apartment in Lower East Side

3.0 star property
7.6 out of 10, Good, (7)
"Our stay was great. The property was at it was described and expected. The owner was available via text and communicated with me when I had questions. We would stay again!"
United States
Vera
ROVE LIVING/KB - Prospect

Condo in Downtown Milwaukee

9.0 out of 10, Wonderful, (46)
"The check in instructions were perfect and not sure he could have laid that out any better. It's a nice place close to everything. We'd stay there again. "
United States
Chad-Tara A.
The price is NZ$576
includes taxes & fees
9 Dec - 10 Dec
Downtown Eastside gem near Fiserv Forum Water St Brady St

Holiday Home in Riverwest

9.6 out of 10, Exceptional, (77)
"He was very kind!"
United States
Hope
The price is NZ$407
includes taxes & fees
9 Dec - 10 Dec
Three bedrooms upstairs

Holiday Home in Bay View

9.6 out of 10, Exceptional, (8)
"Great place!"
United States
Kathy R.
The price is NZ$802
includes taxes & fees
14 Dec - 15 Dec
Pink Diamond Rental in Bayview area Milwaukee with WiFi, AC for pink lovers

Holiday Home in Lower East Side

9.8 out of 10, Exceptional, (31)
"It was a great place and close to Brady street! Definitely recommend. "
United States
Hugh L.
The price is NZ$934
includes taxes & fees
9 Dec - 10 Dec
Stunning Upscale Retreat - Steps From Everything

Holiday Home in Downtown Milwaukee

9.6 out of 10, Exceptional, (23)
"Great house - big group I stayed with loved it and tons of places to sleep and hang out. Fantastic location by the water and near some good restaurants. Hosts were super responsive. "
United States
Henri E.
The price is NZ$2,897
includes taxes & fees
21 Dec - 22 Dec
MKE Mansion - Both Wings

Holiday Home in Johnson Woods

9.8 out of 10, Exceptional, (26)
"We stayed while attending the WI state fair. Quiet and safe neighborhood and really close to the fairgrounds. House was clean and easy to get to. We enjoyed our stay and the fenced in backyard was perfect for our Frenchie. "
United States
Roy W.
The price is NZ$578
includes taxes & fees
9 Dec - 10 Dec
House in Quaint Neighborhood near Downtown Milwaukee Pet-Friendly!

Holiday Home in Burnham Park

9.6 out of 10, Exceptional, (252)
"This spacious house is a true gem, lovingly preserved. Really enjoyed our stay!!!!"
United States
Lynne W.
Frank Lloyd Wright-Designed House In Milwaukee, WI, 4 Bed 2.5 Bath, Sleep10

Holiday Home in Burlington

10.0 out of 10, Exceptional, (146)
"This home on Brown’s Lake checks every box. It is spacious with plenty of space for 12 of us (9 adults and 3 kids) to spread out. The newly remodeled kitchen is amazing (nicer than mine at home) and has every dish, pot, pan or utensil you could ever need. A screened-in 3 season room is off the kitchen with wonderful views of the lake. There are two master bedrooms, but all of the bedrooms are spacious and are located near bathrooms that are lovely. Everyone in our group had their own space...
United States
Linda C.
Island view cottage on crystal clear spring fed lake.

Apartment in Racine

9.6 out of 10, Exceptional, (25)
"We had a wonderful time staying here while visiting the surrounding area!"
United States
Collin C.
The price is NZ$424
includes taxes & fees
9 Dec - 10 Dec
Wisconsin Treehouse Getaway!

Holiday Home in Kenosha

9.6 out of 10, Exceptional, (87)
"Our room was perfect for our weekend visit with friends who lived nearby. The room had everything we needed and was very close to the lake, which has a lovely walking path. Our hosts were kind and helpful."
United States
Julia H.
The price is NZ$191
includes taxes & fees
9 Dec - 10 Dec
Cozy Bedroom with Private Entrance, Bathrm and nearby Lake Michigan View

Holiday Home in Lower East Side

2.0 star property
9.8 out of 10, Exceptional, (19)
"Great property for our family group for a long weekend in Milwaukee. "
United States
Karl S.
The price is NZ$736
includes taxes & fees
9 Dec - 10 Dec
NEW! Fun, style & comfort Eastside MKE Best Day Townhouse 4 bedrooms

Cottage in Salem

3.0 star property
The price is NZ$1,127
includes taxes & fees
9 Dec - 10 Dec
Salem Vacation Home w/ Dock: Steps to Paddock Lake

Holiday Home in Lower East Side

9.6 out of 10, Exceptional, (66)
"Dustin was a great host! Very easy to communicate with and the house was great as well, thanks much!"
United States
Lisa M.
The price is NZ$724
includes taxes & fees
9 Dec - 10 Dec
Stunning Vintage/Modern Brady St Home! Very Walkable, Deck, Fire Pit, Great Find
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Caledonia Hotel Reviews

Find out more about Caledonia

Everything you need to know about Caledonia holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Caledonia holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Caledonia holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Caledonia holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Caledonia. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Caledonia holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Caledonia holiday rentals we have selected for you start as low as NZ$191 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Caledonia rentals

At Expedia, we put the best Caledonia holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Caledonia rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Caledonia holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Caledonia. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Caledonia?

Yes, there are holiday rentals close to the most popular sights in Caledonia, or you can select a more secluded option if you're looking for a relaxing stay. Caledonia is known for its parks.

What are some of the best holiday rentals that Caledonia has to offer?

7 1/2 Acre Estate, Fish Pond, Events! Weddings, MSG Owner for discounts!!!: This highly rated holiday home rental in Caledonia is located on the beach, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

What can I see and do in Caledonia?

While exploring the area, visit family-friendly sights like Crystal Ridge, or get outside and enjoy nature at Boerner Botanical Gardens. In the wider area, you’ll find Milwaukee County Sport Complex and South Milwaukee Downtown Market.

What are holiday rentals like in Caledonia?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Caledonia. Holiday rentals offer amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can offer a sense of privacy away from public hotel lifts and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.