Jackson Vacations from $308

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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.
Holiday Inn Express Hotel & Suites Milwaukee Airport by IHG

Holiday Inn Express Hotel & Suites Milwaukee Airport by IHG

2.5 out of 5
College Heights
Price was $388, price is now $308 per person
$308
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
8/10 Very Good! (972 reviews)
If the dryer is broken and at check in someone asks where the laundry room is at, you should probably mention the dryer is broken! Finding out hours aftet checking in that the dryer is broken is not the time to find out. We wouldve canceled our stay as we needed to wash cloths during our vacation.

Reviewed on Aug 25, 2025

Abbey Resort and Avani Spa

Abbey Resort and Avani Spa

3.5 out of 5
Price was $728, price is now $546 per person
$546
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
New York (JFK) to Milwaukee (MKE)
8.6/10 Excellent! (1,471 reviews)
I was really glad to have found a last minute option, at a fair price.

Reviewed on Aug 25, 2025

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
Price was $631, price is now $488 per person
$488
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.4/10 Exceptional! (1,012 reviews)
Amazing night front desk staff!

Reviewed on Aug 26, 2025

Potawatomi Hotel & Casino

Potawatomi Hotel & Casino

4.5 out of 5
Price was $669, price is now $530 per person
$530
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9/10 Wonderful! (1,340 reviews)
The rooms are very nice and clean. I liked that they had adjoining rooms for two families. Easy uber picked to go to Summerfest grounds.

Reviewed on Aug 25, 2025

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
Price was $634, price is now $508 per person
$508
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Milwaukee (MKE)
9.6/10 Exceptional! (1,698 reviews)
This is a great property to stay at, the hotel is very nice with lots of artwork and ambience. I highly recommend if you’re ever in Milwaukee..

Reviewed on Aug 23, 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
$94 nightly
The price is $104 total per night from Sep 21 to Sep 22
$104 total
Sep 21 - Sep 22
Total with taxes and fees
8.8/10 Excellent! (534 reviews)
"Staff nice"

Reviewed on Aug 16, 2025

Comfort Inn & Suites Jackson - West Bend
Sonesta Milwaukee West Wauwatosa

Sonesta Milwaukee West Wauwatosa

3.5 out of 5
10499 W Innovation Dr, Milwaukee, WI
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Sep 2 to Sep 3
$107 total
Sep 2 - Sep 3
Total with taxes and fees
7.4/10 Good! (1,601 reviews)
"It was actually very comfortable bed needs some updates but still very clean people at the desk were awesome!"

Reviewed on Aug 24, 2025

Sonesta Milwaukee West Wauwatosa
AmericInn by Wyndham Glendale/Milwaukee

AmericInn by Wyndham Glendale/Milwaukee

2.5 out of 5
5110 N Port Washington Rd, (772), Milwaukee, WI
Fully refundableReserve now, pay when you stay
$72 nightly
The price is $83 total per night from Sep 7 to Sep 8
$83 total
Sep 7 - Sep 8
Total with taxes and fees
7.6/10 Good! (1,006 reviews)
"Nice room"

Reviewed on Aug 23, 2025

AmericInn by Wyndham Glendale/Milwaukee
See all 950 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.

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Frequently asked questions

How much does a Jackson vacation package cost?
You'll find cheap prices from $308 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.