
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.

Hawthorn Extended Stay by Wyndham Milwaukee Airport
Price was CA $1,078, price is now CA $948 per person
CA $948
per person
Sep 21 - Sep 27
found 17 hours ago
Roundtrip flight included
Vancouver (YVR) to Milwaukee (MKE)
7.8/10 Good! (939 reviews)
This place is getting pretty run down around the edges. It’s not a great area either the roads are in terrible condition and there isn’t much around.
Reviewed on Jun 29, 2026


Antioch Hotel & Suites
Price was CA $1,105, price is now CA $967 per person
CA $967
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Milwaukee (MKE)
8.8/10 Excellent! (590 reviews)
TV didn't seem to offer the basic channels only a few obscure stations. Other than that glitch eveything was wonderful
Reviewed on Jun 27, 2026

The Iron Horse Hotel
Fifth Ward
Price was CA $1,640, price is now CA $1,451 per person
CA $1,451
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.2/10 Wonderful! (1,176 reviews)
Rooms are good. Lobby is hot and humid. Room AC did not cool to what it was set to, but it wasn’t hot. Would stay again.
Reviewed on Jun 30, 2026

Landing Apartments at Mayfair Collection
Wauwatosa
Price was CA $1,353, price is now CA $1,218 per person
CA $1,218
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
10/10 Exceptional! (4 reviews)
Instructions to find the Serenity apartments at Wauwatosa Wisconsin weren't great but once we found the actual apartment, it exceeded our expectations. It was truly a home away from home, as it was immaculately clean and had everything needed for a fuss free stay. Shops and restaurants witin walking distance.
We highly recommend staying here and will definitely be returning for a longer extended stay!
Reviewed on May 21, 2026
Jackson Hotel Deals

Comfort Inn & Suites Jackson - West Bend
W227 N16890 Tillie Lake Ct Jackson WI
Fully refundable
The price is CA $147 per night from Jul 5 to Jul 6
CA $147
CA $162 total
Jul 5 - Jul 6
includes taxes & fees
9/10 Wonderful! (605 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
The price is CA $150 per night from Jul 5 to Jul 6
CA $150
CA $173 total
Jul 5 - Jul 6
includes taxes & fees
8.4/10 Very good! (925 reviews)
"Location"
Reviewed on Jun 29, 2026

AmericInn by Wyndham Brookfield
16865 W Bluemound Rd Brookfield WI
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Jul 2 to Jul 3
CA $126
CA $146 total
Jul 2 - Jul 3
includes taxes & fees
8/10 Very good! (1,378 reviews)
"Clean and very nice staff. I only needed to stay here for a night cause I live locally but id stay again if needed."
Reviewed on Jun 30, 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.







