Jackson Vacations from $506
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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 Iron Horse Hotel
Fifth Ward
$567
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.2/10 Wonderful! (1,291 reviews)
Great overnight stay at the Iron Horse Hotel! We loved the vibe and atmosphere. The outside dining and entertainment space was excellent! Food was delicious. The rooms were very clean and we enjoyed the industrial touches to the decor. The gym area could use some additional machines. Check in and out was a little confusing and the valet didn’t include the proper charges, so now we need to follow up with the hotel. Kind of annoying. Otherwise, we’re definitely coming back!
Reviewed on Aug 24, 2026
Lake Lawn Resort
$663
per person
Oct 14 - Oct 18
found 12 hours ago
Roundtrip flight included
Dallas (DFW) to Milwaukee (MKE)
9/10 Wonderful! (1,013 reviews)
The Lakeside part of the resort is tucked away from the rest, but we enjoyed having a quiet pool right there. It’s very dated, but well maintained. There are good enough amenities onsite, but the activities and staff involvement could definitely be better. You have to prompt staff and be extremely specific with what you are looking for in order to get anything. For example, despite there being a schedule of activities to participate in, there was never anything going on. Music schedules were off and there was no notice so we had to figure it out on our own. There was supposed to be food and beverage service at the main pool, but there was not. Do not expect anyone to go above and beyond and you will be content. The views were beautiful! Food was ok.
Overall not a bad place to stay at all for the price. I think if staff was more involved and less passive it would be much more pleasurable and we would have spent more time and money on site than we did.
Reviewed on Aug 24, 2026
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundable
$97 nightly
$107 total
Sep 16 - Sep 17
Total with taxes and fees
9/10 Wonderful! (632 reviews)
"Ample parking, food nearby, plenty of towels and pillows, quiet. Appeared to be understaffed. Late start to breakfast and same items offered every day. Good coffee, comfortable bed."
Reviewed on Aug 24, 2026
AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$80 nightly
$93 total
Aug 30 - Aug 31
Total with taxes and fees
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
$110 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,416 reviews)
"The front desk staff was rude, I called ahead and asked for early check in because i"
Reviewed on Aug 24, 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 $506 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.
