Jackson Vacations from $674
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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.
The Ingleside Hotel
Price was $893, price is now $674 per person
$674
per person
Jul 16 - Jul 20
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
8.6/10 Excellent! (800 reviews)
I enjoyed the stay here with a good night sleep, but I would want to have down pillows. All my parties had a good night sleep and they thought it was a very nice hotel.
Reviewed on May 24, 2026
The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $2,019, price is now $1,303 per person
$1,303
per person
Aug 17 - Aug 22
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9.6/10 Exceptional! (2,101 reviews)
Beautiful and historic hotel. The staff is so knowledgeable about the property and willing to share that knowledge. The lobby is such a wonderful place to sit and relax. There are so many places to explore at this property. The art is amazing!
Reviewed on May 24, 2026
Kinn Guesthouse Bay View
Bay View
Price was $1,323, price is now $971 per person
$971
per person
Jul 16 - Jul 20
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.4/10 Exceptional! (462 reviews)
Love the decor. Felt like home! Walking distance to coffee & dinner places was great!
Reviewed on May 8, 2026
Jackson Hotel Deals
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $128 total per night from May 28 to May 29
$128 total
May 28 - May 29
Total with taxes and fees
8.4/10 Very Good! (831 reviews)
"Very clean and the staff was awesome."
Reviewed on May 24, 2026
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from May 27 to May 28
$129 total
May 27 - May 28
Total with taxes and fees
9/10 Wonderful! (1,332 reviews)
"The rooms are extremely outdated and need a complete overhaul."
Reviewed on May 20, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
$116 nightly
The price is $137 total per night from May 26 to May 27
$137 total
May 26 - May 27
Total with taxes and fees
8.6/10 Excellent! (1,311 reviews)
"Hyatt is midpriced but a nice place. Staff is responsive and helpful. Do not engage in parking as that is WAY overpriced. Just spothero someplace cheaper. We parked for 18 dollars total over two nights. The hotel charges 43 dollars per day for valet and 31 dollars a day for self park. Staff WILL ..."
Reviewed on May 24, 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.
