Caledonia Vacations from $236

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Your Caledonia Vacation

Book a Caledonia vacation package and get set to experience this exciting city the easy way. Consider spending some time in the neighborhood of South Milwaukee, which is good for hiking and golfing. If your trip to Caledonia includes a little sightseeing, hit up popular attractions like Milwaukee County Sport Complex, River Bend Nature Center and Franksville Park. Stop daydreaming and start adventuring. Browse the broad range of options on Expedia today and put your Caledonia vacation plans into motion!

The Latest Caledonia vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was $324, price is now $236 per person
$236
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Clean...nice pool n spa area..peaceful

Reviewed on Dec 28, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $736, price is now $542 per person
$542
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
Room ready early. Everything clean and well-kept. Will stay there again.

Reviewed on Jan 7, 2026

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Price was $461, price is now $339 per person
$339
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
The cleanness of the room, the staff accessibility to everything that was a very nice stay.

Reviewed on Jan 1, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $534, price is now $396 per person
$396
per person
Feb 19 - Feb 22
found 6 hours ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $515, price is now $393 per person
$393
per person
Feb 19 - Feb 22
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Milwaukee (MKE)
9.6/10 Exceptional! (1,786 reviews)
Everything was wonderful. Loved the pool.

Reviewed on Jan 9, 2026

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Discover the most popular places to visit in Caledonia

Harley-Davidson Museum showing interior views

Harley-Davidson Museum

4.5/5(337 reviews)

Delve into the history of one of the world’s most famous motorcycle brands via interactive exhibits, photo galleries, workshops and behind-the-scenes tours.

Harley-Davidson Museum
Milwaukee County Zoo featuring interior views and zoo animals as well as a small group of people

Milwaukee County Zoo

4.5/5(217 reviews)

This sprawling animal park houses a wide array of exotic wildlife, and is acclaimed for its conservation programs and educational resources.

Milwaukee County Zoo
Milwaukee Art Museum

Milwaukee Art Museum

4.5/5(400 reviews)

Peruse a vast collection of classic European and American art in this gallery that is housed in a striking modern building.

Milwaukee Art Museum

What to do in Caledonia

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

The Grand Walk: A Self-Guided Audio Tour through Milwaukee

$9
per adult
80% of travellers recommend
The Grand Walk: A Self-Guided Audio Tour through Milwaukee
At the Pabst, Captain Frederick Pabst can been seen smoking backstage on a ghost tour of Milwaukee with Brew City Ghosts

Milwaukee Morbid Mirrorlight Ghost Tours

$32
per adult
Milwaukee Morbid Mirrorlight Ghost Tours
Milwaukee : Best Street Food Private Tour With A Local Guide

Milwaukee Best Street Food Tour With A Local Guide

$109
per adult
Milwaukee Best Street Food Tour With A Local Guide
See all activities in Caledonia

Caledonia Hotel Deals

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
424 E Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$161 nightly
The price is $189 total per night from Jan 19 to Jan 20
$189 total
Jan 19 - Jan 20
Total with taxes and fees
9.4/10 Exceptional! (1,870 reviews)
Staff amazing

Reviewed on Jan 6, 2026

The Pfister Hotel
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
$128 nightly
The price is $151 total per night from Jan 28 to Jan 29
$151 total
Jan 28 - Jan 29
Total with taxes and fees
9.6/10 Exceptional! (2,519 reviews)
Hotel was clean, unique and fun. Can't be anymore conveniently located for a downtown hotel. Staff was pleasant. Smallest note would be not a fan of the pillows. Also, ice tongs would be great. There was a bottle opener and cork screw, so tongs would be great too to round out the convenience of the ...

Reviewed on Jan 5, 2026

Saint Kate - The Arts Hotel
Drury Plaza Hotel Milwaukee Downtown

Drury Plaza Hotel Milwaukee Downtown

3 out of 5
700 N. Water Street Milwaukee WI
Fully refundableReserve now, pay when you stay
$100 nightly
The price is $118 total per night from Jan 18 to Jan 19
$118 total
Jan 18 - Jan 19
Total with taxes and fees
9.6/10 Exceptional! (2,020 reviews)
Everything is top tier, would definitely stay here again.

Reviewed on Jan 5, 2026

Drury Plaza Hotel Milwaukee Downtown
See all 1,174 properties in Caledonia
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.

Find the Best Caledonia Vacation Packages

Caledonia Essential Information

Language
English
Currency
U.S dollars
Closest Airport
General Mitchell Intl. Airport (MKE)
Population
24,700
Top Sights
Racine Zoological Gardens, Rock Snow Park and Racine Art Museum

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Frequently asked questions

How much does a Caledonia vacation package cost?
You can pick up a vacation package to this top destination from $236 on Expedia. However, how much your vacation to Caledonia costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Caledonia?
January, October and December are the best times to search for cheap Caledonia vacation packages. Choosing to travel in quieter periods means you can usually find lower prices on flights and hotels.
How many days is enough for Caledonia?
The ideal duration for your Caledonia vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you plenty of time to go to all the top attractions and explore some hidden gems along the way.
How to find the best Caledonia package deals?
Use Expedia's filter tool to help you find some unbeatable Caledonia package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Caledonia package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Caledonia vacation as a package?
You can enjoy significant savings on your Caledonia getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Caledonia?
If you have your Caledonia travel dates locked in, book early to score some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are ideal for traveling on a whim.
Does Expedia offer Book Now, Pay Later Caledonia vacation packages?
Secure your dream getaway to Caledonia with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait until payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to split the cost across 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to stay on budget and snap up travel deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.