Jackson Vacations from $770
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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.
Kinn Guesthouse Bay View
Bay View
Save 100% on your flight
Price was $1,702, price is now $1,137 per person
$1,137
per person
Jul 17 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
9.4/10 Exceptional! (460 reviews)
Love the decor. Felt like home! Walking distance to coffee & dinner places was great!
Reviewed on May 8, 2026
Holiday Inn Express Milwaukee Downtown by IHG
Downtown Milwaukee
Save 100% on your flight
Price was $1,524, price is now $1,027 per person
$1,027
per person
Jul 17 - Jul 22
found 10 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
9/10 Wonderful! (1,004 reviews)
The room was very large and nice. Very clean. The bed was comfortable. The breakfast was outstanding.
I had trouble with the lighting. There was a master switch that had to be turned on or some of the lights wouldn’t work. Also the air conditioner was very loud but I just turned it off as the room was cold.
I was not told that there would be an additional $39 parking fee added on to the room charge. This upset me. The manager seemed to think that everyone should know that you have to pay to park in a big city. I thought the motel would have a parking garage that would be included in the room cost. The manager gave me a discount since I was upset. Very kind of her.
Reviewed on May 11, 2026
Landing Apartments at Mayfair Collection
Wauwatosa
Save 100% on your flight
Price was $1,367, price is now $1,003 per person
$1,003
per person
Jul 1 - Jul 8
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Milwaukee (MKE)
10/10 Exceptional! (2 reviews)
Beautiful apartment, great lication
Reviewed on Apr 14, 2026
Jackson Hotel Deals
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from May 24 to May 25
$119 total
May 24 - May 25
Total with taxes and fees
8.4/10 Very Good! (798 reviews)
Parking safe.
Reviewed on May 13, 2026
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$90 nightly
The price is $106 total per night from May 28 to May 29
$106 total
May 28 - May 29
Total with taxes and fees
9/10 Wonderful! (1,324 reviews)
My time at the hotel was great. My room was clean and the bed was very comfy. Everyone there was so nice and friendly from the moment I checked in. The bar was a great place to stop after a long day to have a few drinks and pleasant conversation with the bar tender. The manager, Nikki, was exceptional! ...
Reviewed on May 14, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $116 total per night from May 24 to May 25
$116 total
May 24 - May 25
Total with taxes and fees
8.6/10 Excellent! (1,300 reviews)
Good
Reviewed on May 13, 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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
