Jackson Vacations from $321

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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

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
Price was $411, price is now $321 per person
$321
per person
Jan 9 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.8/10 Exceptional! (2,425 reviews)
Nice hotel with some unique artsy touches but the walls are absolutely paper thin so we heard neighbors on both sides (one group of drunk and merry ladies and one fighting couple and their TV). Some soundproofing would be nice.

Reviewed on Dec 7, 2025

DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Price was $499, price is now $361 per person
$361
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Breakfast was advertised as free but it was $15

Reviewed on Dec 7, 2025

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
Price was $726, price is now $534 per person
$534
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
9.6/10 Exceptional! (428 reviews)
The room was great, location was perfect. I loved the loft vibe and exposed brick. It would have been a 5 star review if the TV was working. We couldn't get the TV to turn on.

Reviewed on Nov 5, 2025

Holiday Inn Express Milwaukee Downtown by IHG

Holiday Inn Express Milwaukee Downtown by IHG

2.5 out of 5
Downtown Milwaukee
Price was $645, price is now $481 per person
$481
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
9/10 Wonderful! (1,002 reviews)
Le daría un 5 estrellas. Pero como es general le quito la estrella que falta por no tener el agua caliente de la ducha. Está tibia ni caliente. Recuerdan donde vivimos y el frío que hace para no tener un ma ducha caliente que darte. Por todo lo demás me encantó

Reviewed on Nov 14, 2025

The Iron Horse Hotel

The Iron Horse Hotel

4 out of 5
Fifth Ward
Price was $953, price is now $712 per person
$712
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Charlotte (CLT) to Milwaukee (MKE)
9.2/10 Wonderful! (1,008 reviews)
All was excellent except for 2x items: -No bottled water in room!!?? -Rooms were spotless and beautiful but the lighting was horrible. Someone tried really hard to be fancy and it ain’t working -But I’d stay there again

Reviewed on Dec 7, 2025

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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
$87 nightly
The price is $96 total per night from Dec 21 to Dec 22
$96 total
Dec 21 - Dec 22
Total with taxes and fees
8.8/10 Excellent! (563 reviews)
Stained carpet in my room.

Reviewed on Dec 3, 2025

Comfort Inn & Suites Jackson - West Bend
Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
139 E Kilbourn Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $170 total per night from Dec 30 to Dec 31
$170 total
Dec 30 - Dec 31
Total with taxes and fees
9.6/10 Exceptional! (2,451 reviews)
We always enjoy our stay at St Kate’s

Reviewed on Dec 4, 2025

Saint Kate - The Arts 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 $109 total per night from Dec 10 to Dec 11
$109 total
Dec 10 - Dec 11
Total with taxes and fees
8.4/10 Very Good! (1,212 reviews)
Great hotel. Ideal location

Reviewed on Nov 29, 2025

Hyatt Regency Milwaukee
See all 939 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 $321 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.