Jackson Vacations from $458

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.
Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

Holiday Inn Express & Suites Milwaukee - Brookfield by IHG

2.5 out of 5
Price was $492, price is now $458 per person
$458
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.4/10 Exceptional! (898 reviews)
Quiet and comfortable. Great night's sleep.

Reviewed on Jan 21, 2026

Kasa Westown Milwaukee

Kasa Westown Milwaukee

4 out of 5
Westown
Price was $527, price is now $458 per person
$458
per person
Mar 21 - Mar 24
found 1 day ago
Roundtrip flight included
New York (NYC) to Milwaukee (MKE)
9/10 Wonderful! (116 reviews)
Everything was great . Very clean,parking was good .

Reviewed on Feb 2, 2026

Aloft Milwaukee Downtown

Aloft Milwaukee Downtown

3 out of 5
Westown
Price was $648, price is now $588 per person
$588
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
8.6/10 Excellent! (1,004 reviews)
Clean, a good experience overall. The valet staff was very friendly and professional.

Reviewed on Jan 24, 2026

Dubbel Dutch

Dubbel Dutch

3 out of 5
Downtown Milwaukee
Price was $675, price is now $617 per person
$617
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
9.2/10 Wonderful! (146 reviews)
There is a bar in the building that is loud until midnight. The parking fee was higher than the site warranted. The sofa couch was not suitable for any over 5' tall. It all depends on the room you get in terms of the experience. I would not stay there again, as it was more costly and had little to recommend it. No microwave in the room. Fridge froze my food overnight, making it useless and uneatable. NOT appropriate if you cannot walk up steps easily. I think a regular hotel room would have offered better service at a more reasonable price.

Reviewed on Oct 28, 2025

Grandstay Residential Suites Hotel - Sheboygan

Grandstay Residential Suites Hotel - Sheboygan

2.5 out of 5
Downtown Sheboygan
Price was $550, price is now $513 per person
$513
per person
Mar 20 - Mar 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Milwaukee (MKE)
8.6/10 Excellent! (1,001 reviews)
Great start!! Will be back!

Reviewed on Jan 16, 2026

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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
$79 nightly
The price is $87 total per night from Feb 23 to Feb 24
$87 total
Feb 23 - Feb 24
Total with taxes and fees
8.8/10 Excellent! (574 reviews)
Staff was great and the room was clean. What more do you want!

Reviewed on Jan 18, 2026

Comfort Inn & Suites Jackson - West Bend
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$121 nightly
The price is $142 total per night from Feb 9 to Feb 10
$142 total
Feb 9 - Feb 10
Total with taxes and fees
9.6/10 Exceptional! (2,545 reviews)
Excellent stay there !

Reviewed on Feb 1, 2026

Saint Kate - The Arts Hotel
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$69 nightly
The price is $81 total per night from Feb 23 to Feb 24
$81 total
Feb 23 - Feb 24
Total with taxes and fees
9/10 Wonderful! (1,288 reviews)
Room was clean and staff was amazing!

Reviewed on Jan 29, 2026

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
See all 894 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.

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 $458 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.