Jackson Vacations from $474
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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.
Saint Kate - The Arts Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $689, price is now $474 per person
$474
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
Nice clean room. Fun hotel with great food and next to the theatre!
Reviewed on Jul 9, 2026
The Pfister Hotel
Downtown Milwaukee
Save 100% on your flight
Price was $1,098, price is now $601 per person
$601
per person
Aug 10 - Aug 14
found 1 day ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Beautiful property. Every staff member--from front desk, bar, restaurant, housekeeping, concierge,to bellhops, were pleasant, professional & helpful. Our room was comfortable, clean & quiet. The location was perfect, just a short walk from the art museum. Would certainly stay here again.
Reviewed on Jul 9, 2026
Kinn Guesthouse Bay View
Bay View
Price was $918, price is now $672 per person
$672
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milwaukee (MKE)
9.4/10 Exceptional! (481 reviews)
Great place! Loved that bar and restaurant on site too.
Reviewed on Jul 3, 2026
Kimpton Journeyman Hotel by IHG
Downtown Milwaukee
Price was $1,135, price is now $926 per person
$926
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip flight included
Phoenix (PHX) to Milwaukee (MKE)
9.4/10 Exceptional! (1,001 reviews)
Very friendly staff. Our room was very large compared to other rooms I have stayed in. The bathrooms were also large and very clean. The restaurant in the hotel and the rooftop bar were both really nice. Great ambiance and it is really close to the shops and restaurants in the Third Ward. We took a nice walk along the riverfront, went to the Public market, and saw a show a the Riverside Theater. Everything was very close to the hotel. We really enjoyed staying there!
Reviewed on Jul 8, 2026
Hilton Garden Inn Milwaukee Northwest Conference Center
Park Place
Price was $630, price is now $520 per person
$520
per person
Aug 18 - Aug 24
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Milwaukee (MKE)
8/10 Very Good! (881 reviews)
The room was not ready when wevarrived at 5:30pm it was very noisey banging and bumping overtop our head and room on left side so diasppoint told front desk but they check but said there was nothing they could really do ask for discount but that didnt happen either feel like hotel did not follow there policy even tho book with hotel.com still some acommdation should happen. Really disappointed.
Cleanliness was awesome so was the housekeeper.
Reviewed on Jun 30, 2026
Jackson Hotel Deals
Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $112 total per night from Aug 2 to Aug 3
$112 total
Aug 2 - Aug 3
Total with taxes and fees
9/10 Wonderful! (606 reviews)
"No elevator. I walked the entire first floor twice thinking I somehow missed seeing the elevator. I finally asked the front desk where it was and was told there isn’t one. I don’t mind using the stairs but when you load the dolly cart full and push it down the hallway to use the elevator it would ..."
Reviewed on Jun 28, 2026
Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $119 total per night from Jul 19 to Jul 20
$119 total
Jul 19 - Jul 20
Total with taxes and fees
8.4/10 Very Good! (958 reviews)
"Room was unready for guests, specifically the shower curtain and lack of drainage in the bathtub. Our selected room was not ready at 8p upon arrival and we were told it would take another 2-3 hours before it would be ready so we were a little disappointed. Otherwise, bed was comfortable and check ..."
Reviewed on Jul 8, 2026
Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $110 total per night from Aug 9 to Aug 10
$110 total
Aug 9 - Aug 10
Total with taxes and fees
8.6/10 Excellent! (1,345 reviews)
"Staff was very helpful and polite."
Reviewed on Jul 9, 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.
