Jackson Vacations from $306

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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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Save 100% on your flight
Price was $527, price is now $306 per person
$306
per person
Feb 2 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Breakfast was advertised as free but it was $15

Reviewed on Dec 7, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Save 100% on your flight
Price was $839, price is now $530 per person
$530
per person
Feb 2 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,093, price is now $710 per person
$710
per person
Feb 2 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Great check in, efficient

Reviewed on Dec 15, 2025

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $687, price is now $463 per person
$463
per person
Feb 2 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Manager very helpful when our heat and phone did not work

Reviewed on Dec 11, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $900, price is now $608 per person
$608
per person
Feb 2 - Feb 8
found 11 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
The iron horse hotel stay was wonderful. Special shout out to Maze, Kyle and and Maurice that went above and beyond to make my stay and my dog Hazel’s stay wonderful.

Reviewed on Dec 14, 2025

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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
$87 nightly
The price is $96 total per night from Dec 28 to Dec 29
$96 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (564 reviews)
Stained carpet in my room.

Reviewed on Dec 3, 2025

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
$128 nightly
The price is $151 total per night from Dec 28 to Dec 29
$151 total
Dec 28 - Dec 29
Total with taxes and fees
9.6/10 Exceptional! (2,461 reviews)
Very fun artsy hotel in Milwaukee theater district. Good live music in the bar. An abundance of original art work on display. Very good restaurant.

Reviewed on Dec 10, 2025

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
$74 nightly
The price is $87 total per night from Dec 28 to Dec 29
$87 total
Dec 28 - Dec 29
Total with taxes and fees
9/10 Wonderful! (1,262 reviews)
Room was clean and spacious. However the toilets are very small and very low to ground. I felt like I was in an elementary school bathroom. It is good thing we have good knees. The only other thing was the water was not what I would consider hot in the shower, although warm enough just not a hot ...

Reviewed on Dec 8, 2025

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
See all 947 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 $306 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.