
Jackson Vacation Packages
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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.
Top Jackson Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Potawatomi Hotel & Casino
Menomonee River Valley
Price was CA $2,367, price is now CA $1,924 per person
CA $1,924
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,498 reviews)
Front desk staff nice but I was told hotel gave me $20 credit for EACH of our 2 nites, for use on sundries, etc. He said must use separately each day. Now only 1 of 2 vouchers credited. Phoned hotel, no help except email suggestion. No response from hotel on my emails yet.
Reviewed on Jun 1, 2026

The Iron Horse Hotel
Fifth Ward
Price was CA $3,146, price is now CA $2,444 per person
CA $2,444
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.2/10 Wonderful! (1,139 reviews)
Overall a great experience. The curtains in the room didn’t close all the way so the sun was glaring at us by 6am.
Reviewed on May 31, 2026

Kinn Guesthouse Bay View
Bay View
Price was CA $2,674, price is now CA $2,152 per person
CA $2,152
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9.4/10 Exceptional! (464 reviews)
Kinn Guesthouses are a great place to stay if you don’t mind no front desk and coded entries. We’ve found them to have large rooms which are tastefully decorated, comfortable and quiet. The common area is stocked with teas, coffee and breakfast cereals which you can use.
Be sure to contact property directly before you arrive for entry code. Expedia apparently does not share contact information with Kinn so you can access the room. Therefore they have no way to send you this information This can result in check-in delay until you find a person affiliated with Kinn to update you with this info.
Reviewed on May 29, 2026

Hilton Milwaukee
Westown
Price was CA $3,238, price is now CA $2,615 per person
CA $2,615
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
8.6/10 Excellent! (1,167 reviews)
Hotel was very clean and well organized. The decor was pretty. Staff was friendly and helpful. We used in room dining and the food was good. Ate twice at on site restaurant and that food was good. Parking was easy. Hotel was close to everything.
Reviewed on May 26, 2026

Holiday Inn Express Milwaukee Downtown by IHG
Downtown Milwaukee
Price was CA $2,537, price is now CA $2,068 per person
CA $2,068
per person
Aug 3 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Milwaukee (MKE)
9/10 Wonderful! (1,006 reviews)
The breakfast was very good. The staff was very helpful with the parking situation. Our only negative is that my husband has a c pap machine to sleep. There is a master switch for all the outlets and lights on the bed wall. When the switch was turned off the c pap wouldn’t work without the light staying on behind the bed. We finally did find an outlet on the opposite wall and had an extension cord so it worked.
Reviewed on May 31, 2026
Jackson Hotel Deals

Sheraton Milwaukee Brookfield Hotel
375 S Moorland Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $146 per night from Jun 28 to Jun 29
CA $146
CA $169 total
Jun 28 - Jun 29
includes taxes & fees
8.4/10 Very Good! (862 reviews)
"Clean Room.friendly staff"
Reviewed on May 31, 2026

Saint Kate - The Arts Hotel
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $275 per night from Jun 7 to Jun 8
CA $275
CA $324 total
Jun 7 - Jun 8
includes taxes & fees
9.8/10 Exceptional! (2,632 reviews)
"We love staying here for our anniversary every year! Awesome staff! Doua was super helpful and we will be back!"
Reviewed on Jun 1, 2026

Hyatt Regency Milwaukee
333 W Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 10 to Jun 11
CA $192
CA $227 total
Jun 10 - Jun 11
includes taxes & fees
8.6/10 Excellent! (1,320 reviews)
"After a long day on two wheels i found this room way above my expectations. The room was spacious and comfortable. The inviting warmth of the room could be fine tuned with some artwork on the walls. Breakfast was as expected and hit the spot for someone on the go. Breakfast included the typical folded ..."
Reviewed on Jun 1, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.







