Jackson Vacations from $543
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
Price was $647, price is now $543 per person
$543
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) 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
Hilton Milwaukee
Westown
Price was $769, price is now $646 per person
$646
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
8.4/10 Very Good! (1,075 reviews)
I really liked how nice the hotel looked. And the staff were very helpful. And I did enjoy playing with the doggies when they were around:)
Reviewed on Dec 7, 2025
Saint Kate - The Arts Hotel
Downtown Milwaukee
Price was $686, price is now $605 per person
$605
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Beautiful hotel, great value. Centered around theaters. Lively nightlife and bar. Delicious breakfast. Arts atmosphere feels kind of like you're staying in a museum or gallery for the evening.
Reviewed on Dec 17, 2025
The Brewhouse Inn & Suites
Westown
Price was $654, price is now $579 per person
$579
per person
Jan 23 - Jan 25
found 1 day ago
Roundtrip non-stop flight included
Philadelphia (PHL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
Excellent experience. Employees super friendly and the rooms were exceptional
Reviewed on Dec 17, 2025
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundableReserve now, pay when you stay
$84 nightly
The price is $93 total per night from Dec 28 to Dec 29
$93 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (565 reviews)
Mostly processed food. Not a lot of variety.
Reviewed on Dec 11, 2025
Saint Kate - The Arts Hotel
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! (2,482 reviews)
Great check in, efficient
Reviewed on Dec 15, 2025
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$74 nightly
The price is $87 total per night from Jan 2 to Jan 3
$87 total
Jan 2 - Jan 3, 2026
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
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 |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
