Jackson Vacations from $327

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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.
DoubleTree by Hilton Milwaukee - Brookfield

DoubleTree by Hilton Milwaukee - Brookfield

4 out of 5
Save 100% on your flight
Price was $539, price is now $327 per person
$327
per person
Feb 2 - Feb 8
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) 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
Save 100% on your flight
Price was $855, price is now $570 per person
$570
per person
Feb 2 - Feb 8
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) 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

Kimpton Journeyman Hotel by IHG

Kimpton Journeyman Hotel by IHG

4.5 out of 5
Downtown Milwaukee
Save 100% on your flight
Price was $932, price is now $682 per person
$682
per person
Feb 2 - Feb 8
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
9.4/10 Exceptional! (925 reviews)
Definitely “overrated”! Expectation shattered! Very expensive! Facility is old and worn and could use updating. Location will be nice very soon following construction. Close to the River Walk which is nice weather permitting.

Reviewed on Oct 21, 2025

Wildwood Lodge

Wildwood Lodge

2.5 out of 5
Price was $544, price is now $405 per person
$405
per person
Feb 2 - Feb 8
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
8.4/10 Very Good! (1,001 reviews)
Extremely welcoming friendly staff Good pool very clean and quiet Nice room and bathroom Easy/ accessible Parking outside hotel

Reviewed on Dec 13, 2025

Fairfield Inn & Suites by Marriott Milwaukee Brookfield

Fairfield Inn & Suites by Marriott Milwaukee Brookfield

2.5 out of 5
Price was $521, price is now $402 per person
$402
per person
Feb 2 - Feb 8
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to Milwaukee (MKE)
8.8/10 Excellent! (419 reviews)
The facility seems to be fairly new and well cared for. Staff were friendly. The breakfast is as good as anything you would get in a restaurant. My only concern was the weekend that I stayed was extremely cold. I believe the high temperature was 4° with a hefty wind. The window in my room did not seem to be well caulked. It was difficult with the wind coming in around the edges of that window to maintain a comfortable temperature in the room My last night there I packed the extra pillows into the window and secured it with hangers from the closet.

Reviewed on Dec 14, 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
$84 nightly
The price is $93 total per night from Dec 28 to Dec 29
$93 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (565 reviews)
Mostly processed food. Not a lot of variety.

Reviewed on Dec 11, 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
$128 nightly
The price is $151 total per night from Dec 28 to Dec 29
$151 total
Dec 28 - Dec 29
Total with taxes and fees
9.6/10 Exceptional! (2,482 reviews)
Great check in, efficient

Reviewed on Dec 15, 2025

Saint Kate - The Arts Hotel
Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham

4 out of 5
2308 W Wisconsin Ave Milwaukee WI
Fully refundableReserve now, pay when you stay
$68 nightly
The price is $80 total per night from Dec 29 to Dec 30
$80 total
Dec 29 - Dec 30
Total with taxes and fees
9/10 Wonderful! (1,260 reviews)
The room was very clean and the staff was extremely helpful and kind. I was greeted right away and taken to the front desk to check in. The atmosphere in this beautiful building is wonderful!

Reviewed on Dec 17, 2025

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
See all 945 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 $327 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.