Jackson Vacations from $402
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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
Price was $504, price is now $402 per person
$402
per person
Jan 2 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
16.8/10 Exceptional! (1,001 reviews)
Clean room, most comfortable bed and pillows I’ve experienced in a hotel. There’s a bar and grill that offer food! Staff was very knowledgeable and pleasant.
Reviewed on Nov 17, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was $666, price is now $495 per person
$495
per person
Jan 2 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
19.6/10 Exceptional! (2,425 reviews)
The check-in was seamless. Nacho was so friendly and helpful! Our room was amazing! We couldn’t be happier!
Reviewed on Nov 24, 2025
Potawatomi Hotel & Casino
Menomonee River Valley
Price was $817, price is now $629 per person
$629
per person
Jan 2 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
18/10 Exceptional! (1,357 reviews)
The hotel was beautiful, the room was super clean and the staff were super nice! Very good experience!
Reviewed on Nov 21, 2025
The Iron Horse Hotel
Fifth Ward
Price was $649, price is now $526 per person
$526
per person
Jan 2 - Jan 5
found 13 hours ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
18.4/10 Exceptional! (1,008 reviews)
All was great. Great staff, great room. Would definitely stay there again.
Reviewed on Nov 16, 2025
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundableReserve now, pay when you stay
$92 nightly
The price is $101 total per night from Dec 4 to Dec 5
$101 total
Dec 4 - Dec 5
Total with taxes and fees
8.8/10 Excellent! (559 reviews)
The stay was ok, except the toilet got clogged several times, and they gave me a plunger to open the drain by myself. The sink also drained slow. The heater wasn't working properly, it was extremely hot. They're thankfully pet friendly though. My dog enjoyed the stay.
Reviewed on Nov 17, 2025
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Nov 26 to Nov 27
$109 total
Nov 26 - Nov 27
Total with taxes and fees
8.4/10 Very Good! (1,201 reviews)
The staff was really nice and helpful. The room was clean and it’s in a great location.
Reviewed on Nov 18, 2025
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $122 total per night from Dec 21 to Dec 22
$122 total
Dec 21 - Dec 22
Total with taxes and fees
9.6/10 Exceptional! (2,432 reviews)
Great hotel. Clean. Close to everything.
Reviewed on Nov 21, 2025
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.
