Jackson Vacations from $542
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Your Jackson Vacation
Unforgettable adventures await when you reserve a vacation package to Jackson. Whether you're a history buff, foodie or just a traveler who loves discovering new places, there's something for everyone in this exciting city. Fill your free time with visits to Little Switzerland, Cabelas and Kettle Moraine Ice Center, some of the top attractions you shouldn't miss during a trip to Jackson. Expedia is here to help you escape your routine. Tailor your vacation to Jackson to suit your travel style, whatever that may be.
The Latest Jackson vacation packages
Price found within the past 48 hours. Click for updated prices.
The Ingleside Hotel
$640
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
8.6/10 Excellent! (927 reviews)
The staff was really polite, the room was clean but it smelled of weed so badly. Everytime you stepped outside of your room it was an instant headache. Everything else was good.
Reviewed on Sep 14, 2026
Schuster Mansion Bed & Breakfast
Concordia
$689
per person
Nov 26 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
9.2/10 Wonderful! (329 reviews)
The bed and breakfast were very conveniently located to the actuations we came to see and do.
Reviewed on Sep 13, 2026
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundableReserve now, pay when you stay
$97 nightly
$107 total
Oct 6 - Oct 7
Total with taxes and fees
9/10 Wonderful! (638 reviews)
"The property was nice and presentable. Bed was comfortable. Breakfast was plenty."
Reviewed on Sep 13, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
$110 total
Sep 29 - Sep 30
Total with taxes and fees
8.6/10 Excellent! (1,457 reviews)
"Great location, friendly staff"
Reviewed on Sep 14, 2026
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$78 nightly
$90 total
Sep 16 - Sep 17
Total with taxes and fees
8/10 Very Good! (1,596 reviews)
"There was no information in the room. Telephone book,info on area, room info."
Reviewed on Sep 15, 2026
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 Jackson Vacation Packages
Jackson Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | General Mitchell Intl. Airport (MKE) |
Population | 6,900 |
Max Temp Winter | 25ºF |
Max Temp Summer | 75ºF |
Top Sights | Little Switzerland, Cedar Creek Winery and Sunburst Ski Area |
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Frequently asked questions
How much does a Jackson vacation package cost?
You'll find cheap prices from $542 on Expedia for your Jackson break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Jackson costs.
What are the cheapest months to go to Jackson?
You're likely to find lower prices and better availability in April, September and October. Check out our cheap Jackson vacation packages and you could get some great off-season discounts.
How many days is enough for Jackson?
Typically, a handful of days is enough to visit the major sights during your Jackson vacation. But if you want to have time to chill out or go on day tours, think about extending your trip.
How to find the best Jackson package deals?
Use Expedia's handy filters to find some of the best Jackson package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Jackson package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Jackson vacation as a package?
You can enjoy significant savings on your Jackson getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value 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 Jackson?
If you're planning a spur-of-the-moment Jackson vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Jackson vacation packages?
Set off on your dream escape to Jackson with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up cheap 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.
