
Jackson Vacations from $344
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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 Brewhouse Inn & Suites
Westown
Price was $450, price is now $344 per person
$344
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,013 reviews)
The property and rooms are beautiful, especially if you are a beer enthusiast as the building is the former Pabst historic brewhouse. The surrounding area takes advantage of this theme, including breweries within a stone’s throw of the hotel.
Reviewed on Oct 19, 2025

Saint Kate - The Arts Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $637, price is now $455 per person
$455
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Spacious room, comfortable bed. Love that when you check in they give you a glass of wine. The bar downstairs is a vibe and stays busy but did not disturb the quietness when I was in my room. Loved the art area in the hotel, I got to meet a local artist. This hotel is located near a lot of restaurants and stores within walkable distance. I parked the rental car and basically walked everywhere.
Reviewed on Oct 24, 2025


Kinn Guesthouse Bay View
Bay View
Save 100% on your flight
Price was $512, price is now $379 per person
$379
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.6/10 Exceptional! (418 reviews)
Overall nice, but recommend traveling light since there is no elevator. A bit frustrating that the thermostat reset every few hours. Parking is incredibly limited and we had to get permission to use the handicap spot. The shower head holder was broken rendering it useless, and the beds and pillows weren't very comfortable. All that said, it's a pretty place and well decorated. We also enjoyed the experience of a hotel with the convenience of a VRBO. The staff we corresponded with briefly was super friendly. We would stay again, albeit with slightly nerfed expectations.
Reviewed on Oct 19, 2025

The Pfister Hotel
Downtown Milwaukee
Price was $573, price is now $445 per person
$445
per person
Dec 1 - Dec 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.6/10 Exceptional! (1,771 reviews)
Very nice historic downtown hotel. Small room but comfortable and nicely decorated. Bed was comfortable! Best hotel out of all the ones we stayed in during our vacation.
Reviewed on Oct 23, 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 Nov 9 to Nov 10
$106 total
Nov 9 - Nov 10
Total with taxes and fees
8.8/10 Excellent! (550 reviews)
Front desk attendant was frendly and profesional. Room was very nice. We will stay here again.
Reviewed on Oct 12, 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 Nov 2 to Nov 3
$102 total
Nov 2 - Nov 3
Total with taxes and fees
7.4/10 Good! (1,748 reviews)
Great job 👍
Reviewed on Oct 23, 2025

Holiday Inn Express Milwaukee-West Medical Center by IHG
11111 W North Ave, Milwaukee, WI
Fully refundable
$98 nightly
The price is $114 total per night from Oct 27 to Oct 28
$114 total
Oct 27 - Oct 28
Total with taxes and fees
7.6/10 Good! (1,024 reviews)
It was great, clean, friend staff. Only complaint is our shower was very hard to turn on and we had to ask for a shower curtain bc the bathroom didnt have one.
Reviewed on Oct 19, 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.


















