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

Hawthorn Extended Stay by Wyndham Milwaukee Airport

3 out of 5
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

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was CA $1,546, price is now CA $1,285 per person
CA $1,285
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Milwaukee (MKE)
9.8/10 Exceptional! (2,669 reviews)
Excellent hotel

Reviewed on Jun 30, 2026

Antioch Hotel & Suites

Antioch Hotel & Suites

3 out of 5
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

The Iron Horse Hotel

4 out of 5
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

Landing Apartments at Mayfair Collection

4 out of 5
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

Ready to book your vacation to Jackson?

 

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Jackson Hotel Deals

Comfort Inn & Suites Jackson - West Bend

Comfort Inn & Suites Jackson - West Bend

2.5 out of 5
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

Comfort Inn & Suites Jackson - West Bend
Sheraton Milwaukee Brookfield Hotel

Sheraton Milwaukee Brookfield Hotel

3.5 out of 5
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

Sheraton Milwaukee Brookfield Hotel
AmericInn by Wyndham Brookfield

AmericInn by Wyndham Brookfield

3 out of 5
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

AmericInn by Wyndham Brookfield
See all 916 properties in Jackson
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Jackson vacation package cost?
Offering great value package deals from CA $948 on Expedia, you'll be thrilled with how little a vacation to Jackson costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Jackson?
January, February and October are great times to search for cheap Jackson vacation packages. Opting to travel in less busy periods means you can generally find better prices on flights and accommodations.
How many days is enough for Jackson?
Generally, a handful of days is enough to see the main attractions during your Jackson vacation. However, if you want to have more time to kick back or go on day tours, consider extending your trip.
How to find the best Jackson package deals?
Landing a cheap Jackson package deal is a cinch with Expedia. After you've entered your travel dates and destination under our "Packages" tab, set your budget, apply some filters and browse what's available. You can customize your search by "Amenities," "Property type," "Popular locations" and more. Order the results by "Price: low to high" to discover the most pocket-friendly Jackson package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Jackson vacation as a package?
You can enjoy significant savings on your next Jackson break by booking a personalized vacation package. Click on the "Package" heading, then enter your travel dates and destination to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Jackson?
If you've got your Jackson travel dates confirmed, book as soon as you can to grab some awesome deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Jackson?

  1. Choose your travel dates: The things you plan to do in Jackson and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to activities and airfares. Your hotel will probably be the biggest expense during your trip to Jackson.
  3. Decide your trip length: Consider how long you want to spend discovering Jackson. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your airfare and accommodations: Once you've nailed down your trip dates and duration, lock in the perfect Jackson vacation package for you.

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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.