Jackson Vacations from $419

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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.
Hampton Inn & Suites Milwaukee Downtown

Hampton Inn & Suites Milwaukee Downtown

2.5 out of 5
Westown
Price was $564, price is now $419 per person
$419
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Milwaukee (MKE)
6.8/10 (1,008 reviews)
The hotel was in a great location and the breakfast was delicious. The hotel had the friendliest staff ever. Michael was especially nice and talked to us for a while. We would definitely stay here again.

Reviewed on Jul 8, 2026

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $1,216, price is now $755 per person
$755
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Milwaukee (MKE)
9.6/10 Exceptional! (2,139 reviews)
Great staff super helpful

Reviewed on Jul 9, 2026

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $650, price is now $422 per person
$422
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Milwaukee (MKE)
9.8/10 Exceptional! (2,652 reviews)
Only there two nights but really enjoyed it! Room was lovely, breakfast nice, bar good and staff were even better.

Reviewed on Jul 8, 2026

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Save 100% on your flight
Price was $724, price is now $506 per person
$506
per person
Sep 28 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Milwaukee (MKE)
9.2/10 Wonderful! (1,192 reviews)
Very Well Decorated, Very Comfortable.

Reviewed on Jul 9, 2026

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Save 100% on your flight
Price was $807, price is now $570 per person
$570
per person
Sep 23 - Sep 26
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

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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 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

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
$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! (955 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

Sheraton Milwaukee Brookfield Hotel
Hyatt Regency Milwaukee

Hyatt Regency Milwaukee

4 out of 5
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! (1,343 reviews)
"Great amenities such as having Starbucks and vending machine. Overall great location with easy access parking"

Reviewed on Jul 8, 2026

Hyatt Regency Milwaukee
See all 915 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.

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

How much does a Jackson vacation package cost?
You'll find cheap prices from $419 on Expedia for your Jackson break. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Jackson costs.
What are the cheapest months to go to Jackson?
You're likely to find lower prices and better availability in April, September and October. Check out our cheap Jackson vacation packages and you could get some great off-season discounts.
How many days is enough for Jackson?
Typically, a handful of days is enough to visit the major sights during your Jackson vacation. But if you want to have time to chill out or go on day tours, think about extending your trip.
How to find the best Jackson package deals?
Use Expedia's handy filters to find some of the best Jackson package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Jackson package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your vacation package as soon as possible.
Is it cheaper to book a Jackson vacation as a package?
You can enjoy significant savings on your Jackson getaway by booking a personalized vacation package. Check the "Package" heading, then select your destination and travel dates to see the best hotel and flight prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Jackson?
If you're planning a spur-of-the-moment Jackson vacation, browse our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find amazing deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Jackson vacation packages?
Set off on your dream escape to Jackson with help from Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or wait for the next payday — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or extra charges, you can easily stick to your budget and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.