Jackson Vacations from $344

Book a Hotel + Flight or Car together to unlock savings

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 Brewhouse Inn & Suites
Saint Kate - The Arts Hotel
The Delafield Hotel
Kinn Guesthouse Bay View
The Pfister Hotel
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Jackson Hotel Deals

Comfort Inn & Suites Jackson - West Bend

Comfort Inn & Suites Jackson - West Bend

2.5 out of 5
W227 N16890 Tillie Lake Ct, Jackson, WI
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $106 total per night from Nov 9 to Nov 10
$106 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (550 reviews)
Front desk attendant was frendly and profesional. Room was very nice. We will stay here again.

Reviewed on Oct 12, 2025

Comfort Inn & Suites Jackson - West Bend
Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Nov 2 to Nov 3
$102 total
Nov 2 - Nov 3
Total with taxes and fees
7.4/10 Good! (1,748 reviews)
Great job 👍

Reviewed on Oct 23, 2025

Sonesta Milwaukee West Wauwatosa
Holiday Inn Express Milwaukee-West Medical Center by IHG

Holiday Inn Express Milwaukee-West Medical Center by IHG

2.5 out of 5
11111 W North Ave, Milwaukee, WI
Fully refundable
$98 nightly
The price is $114 total per night from Oct 27 to Oct 28
$114 total
Oct 27 - Oct 28
Total with taxes and fees
7.6/10 Good! (1,024 reviews)
It was great, clean, friend staff. Only complaint is our shower was very hard to turn on and we had to ask for a shower curtain bc the bathroom didnt have one.

Reviewed on Oct 19, 2025

Holiday Inn Express Milwaukee-West Medical Center by IHG
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 $344 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.