Jackson Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Jackson

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
The price is S$120 per night from 27 Mar to 28 Mar
S$120
includes taxes & fees
27 Mar - 28 Mar
9/10 Wonderful! (482 reviews)
"Thank you"

Reviewed on 12 Mar,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
The price is S$233 per night from 14 Apr to 15 Apr
S$233
includes taxes & fees
14 Apr - 15 Apr
9.6/10 Exceptional! (2,269 reviews)
"Great hotel. Was able to walk to a verity of places to see and eat"

Reviewed on 19 Mar,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
The price is S$157 per night from 24 Mar to 25 Mar
S$157
includes taxes & fees
24 Mar - 25 Mar
9/10 Wonderful! (1,046 reviews)
"I was satisfied with my stay at this hotel. Will consider it next time I travel to Milwaukee, WI."

Reviewed on 19 Mar,2025

Ambassador Hotel Milwaukee, Trademark Collection by Wyndham
See all 1,000 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.

Frequently asked questions

How much does a Jackson holiday package cost?
You’ll find cheap prices 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 holiday to Jackson costs.
What are the cheapest months to go to Jackson?
You’re likely to find lower rates and greater availability in January, February and October. Take a look at our cheap Jackson holiday packages and you could land some great off-season discounts.
How many days is enough for Jackson?
Typically, a handful of days is enough to tick off the top attractions during your Jackson holiday. But if you’d like to have more time to chill out or take day trips, consider 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 holiday package as soon as possible.
Is it cheaper to book a Jackson holiday as a package?
You can enjoy significant savings on your Jackson getaway by booking a personalised holiday 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 holiday package to Jackson?
If you’re planning a spur-of-the-moment Jackson holiday, 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.
How to plan a trip to Jackson?

  1. Choose your travel dates: The things you plan to do in Jackson and your preferred season will help you decide when to go.
  2. Calculate your budget: Ensure you have enough money to cover everything from dining out and transportation to flights and activities. Your hotel will likely be the largest expense during your trip to Jackson.
  3. Work out your trip length: Think about how long you’d like to spend discovering Jackson. Plan your days so you can get to all the activities and attractions you’re interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a tailored Jackson holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.