Jackson Vacations from $278
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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.
Fairfield Inn & Suites Kenosha Pleasant Prairie
Price was $309, price is now $278 per person
$278
per person
Dec 3 - Dec 6
found 24 hours ago
Roundtrip non-stop flight included
Los Angeles (QLA) to Milwaukee (MKE)
9.2/10 Wonderful! (643 reviews)
There was a glitch in the system and the lady at the front desk helped me out at no extra charge.
Reviewed on Oct 6, 2025
Kinn Guesthouse Bay View
Bay View
Price was $527, price is now $421 per person
$421
per person
Nov 14 - Nov 16
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Milwaukee (MKE)
9.6/10 Exceptional! (411 reviews)
This is a gem of a hotel in Milwaukee. Stayed in Suite #1. High ceilings, exposed brick, clean, overall a great space to come home to when visiting MKE.
Walkable to most of Bay View, so you have lots of options if you don't wanna drive.
Reviewed on Oct 10, 2025
Days Inn by Wyndham Pleasant Prairie Kenosha
Price was $375, price is now $336 per person
$336
per person
Dec 3 - Dec 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Milwaukee (MKE)
8.2/10 Very Good! (316 reviews)
Polite staff. Room met expectations. Good location and cost.
Reviewed on Oct 8, 2025
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct, Jackson, WI
Fully refundableReserve now, pay when you stay
$96 nightly
The price is $106 total per night from Oct 22 to Oct 23
$106 total
Oct 22 - Oct 23
Total with taxes and fees
8.8/10 Excellent! (548 reviews)
"We stayed one night and chose this place based on its location to the sights we were visiting. We spent a day and half at Holy Hill and ate dinner at Fox & Hounds. All very close by. View out of room window was a peaceful field which was a pleasant surprise given our proximity to the highways."
Reviewed on Oct 1, 2025
Sonesta Milwaukee West Wauwatosa
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $102 total per night from Oct 19 to Oct 20
$102 total
Oct 19 - Oct 20
Total with taxes and fees
7.4/10 Good! (1,719 reviews)
"Great place to stay close to what we needed"
Reviewed on Oct 9, 2025
Hyatt Regency Milwaukee
333 W Kilbourn Ave, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $124 total per night from Nov 10 to Nov 11
$124 total
Nov 10 - Nov 11
Total with taxes and fees
8.4/10 Very Good! (1,171 reviews)
"Clean room. Convenient location!"
Reviewed on Oct 8, 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.
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.