Jackson Vacations from $427
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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 Delafield Hotel
Price was $591, price is now $448 per person
$448
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (425 reviews)
The room was big, but pretty cold. The dinner at I.D. was good. There was no breakfast included.
Reviewed on Jan 6, 2026
Woodspring Suites Milwaukee - Menomonee Falls
Park Place
Price was $530, price is now $441 per person
$441
per person
Feb 19 - Feb 23
found 13 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
8.2/10 Very Good! (147 reviews)
Yes, GREAT EXPERIENCE! JUST WONDERFUL RECOMEND.
Reviewed on Jan 13, 2026
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $91 total per night from Feb 8 to Feb 9
$91 total
Feb 8 - Feb 9
Total with taxes and fees
8.8/10 Excellent! (570 reviews)
The room was very clean and spacious. It was also very quiet. My teenagers enjoyed the pool and hot tub. Culver’s is right next door. The staff was very friendly. We forgot our thermos in the room and came back for it 4 hours later. Yes, it was waiting for us.
Reviewed on Jan 1, 2026
Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $128 total per night from Jan 28 to Jan 29
$128 total
Jan 28 - Jan 29
Total with taxes and fees
9.6/10 Exceptional! (2,515 reviews)
Great hotel! So fun and unique. Very clean and personalized
Reviewed on Jan 11, 2026
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $85 total per night from Feb 1 to Feb 2
$85 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (1,270 reviews)
Large, comfortable room. Clean.
Reviewed on Jan 11, 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.
