Jackson Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Ready to book your vacation to Jackson?

 

Choose your dates

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
The price is CA $133 per night from Aug 3 to Aug 4
CA $133
CA $147 total
Aug 3 - Aug 4
includes taxes & fees
8.8/10 Excellent! (517 reviews)
"Nice sized room. Bathroom was nice. My only suggestions would be to have a night light in the bathroom for midnight trips."

Reviewed on Jul. 23, 2025

Comfort Inn & Suites Jackson - West Bend
Sonesta Select Milwaukee Brookfield

Sonesta Select Milwaukee Brookfield

3 out of 5
16865 W Bluemound Rd, Brookfield, WI
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Aug 25 to Aug 26
CA $115
CA $132 total
Aug 25 - Aug 26
includes taxes & fees
8/10 Very Good! (1,191 reviews)
"Another pleasant stay at the Sonesta Select in Brookfield. Breakfast was a little weak, but the room was comfortable and clean."

Reviewed on Jul. 25, 2025

Sonesta Select Milwaukee Brookfield
Four Points by Sheraton Milwaukee North Shore

Four Points by Sheraton Milwaukee North Shore

3 out of 5
8900 N Kildeer Ct, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Aug 3 to Aug 4
CA $141
CA $164 total
Aug 3 - Aug 4
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"I had a lovely evening. Thank you."

Reviewed on Jul. 10, 2025

Four Points by Sheraton Milwaukee North Shore
See all 1,027 properties in Jackson
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Jackson vacation package cost?
Offering great value package deals on Expedia, you'll be thrilled with how little a vacation to Jackson costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Jackson?
January, February and October are great times to search for cheap Jackson vacation packages. Opting to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Jackson?
Generally, a handful of days is enough to see the main attractions during your Jackson vacation. However, if you want to have more time to kick back or go on day tours, consider extending your trip.
How to find the best Jackson package deals?
Landing a cheap Jackson package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Jackson package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Jackson vacation as a package?
You can enjoy significant savings on your next Jackson break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Jackson?
If you've got your Jackson travel dates confirmed, book as soon as you can to grab some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Jackson?

  1. Choose your travel dates: The things you plan to do in Jackson and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will probably be the biggest expense during your trip to Jackson.
  3. Decide your trip length: Consider how long you want to spend discovering Jackson. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the perfect Jackson vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.