Jackson Vacation Packages

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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.

Top Jackson Vacation Deals

Price found within the past 48 hours. Click for updated prices.
The Knickerbocker on the Lake

The Knickerbocker on the Lake

3 out of 5
Downtown Milwaukee
per person
Oct. 27 - Oct. 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
8.4/10 Very Good! (1,009 reviews)
Very historic cool doors.

Reviewed on Sep. 16, 2024

Saint Kate - The Arts Hotel

Saint Kate - The Arts Hotel

4 out of 5
Downtown Milwaukee
per person
Oct. 27 - Oct. 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.8/10 Exceptional! (1,905 reviews)
This hotel is like no other. I barely looked up anything before so has such a fun surprise when I saw the free champagne, art galleries, and artist themes in the rooms. This is truly my favorite hotel I’ve ever visited. I can’t wait to go back!

Reviewed on Sep. 22, 2024

The Brewhouse Inn & Suites

The Brewhouse Inn & Suites

3.5 out of 5
Westown
per person
Oct. 27 - Oct. 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,004 reviews)
Incredible property in an incredible historic building in an incredible historic district to yourself a favor and go to the 2nd floor to see all the original copper kettles from the brewery and watch televised history plane in loops on the walls. The staff was incredibly accommodating especially Eddie and Chloe at the front desk. Update yourself a favor and take PABST tour Just down the block it's worth it. Also make sure you stop at Central waters just next door for some great food and even better beer and a wonderful atmosphere 10 out of 10 recommend

Reviewed on Sep. 17, 2024

The Pfister Hotel

The Pfister Hotel

4.5 out of 5
Downtown Milwaukee
per person
Oct. 27 - Oct. 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.4/10 Exceptional! (1,462 reviews)
The Pfister never disappoints!

Reviewed on Sep. 15, 2024

Kinn Guesthouse Bay View

Kinn Guesthouse Bay View

4.5 out of 5
Bay View
per person
Oct. 27 - Oct. 30
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Milwaukee (MKE)
9.6/10 Exceptional! (343 reviews)
We loved the room and property. It was easy to get to and park at. The ameneties were great!

Reviewed on Sep. 16, 2024

Ready to book your vacation to Jackson?

 

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Jackson Hotel Deals

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 CA $205 per night from Oct. 6 to Oct. 7
CA $205
CA $241 total
includes taxes & fees
Oct 6 - Oct 7
9.6/10 Exceptional! (1,905 reviews)
"Elegant, comfortable, and customer service plus!"

Reviewed on Sep. 18, 2024

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
The price is CA $164 per night from Oct. 6 to Oct. 7
CA $164
CA $194 total
includes taxes & fees
Oct 6 - Oct 7
8.2/10 Very Good! (1,124 reviews)
"Was a little perturbed with my reserved and paid for room not being ready. I arrived about 30 minutes before check-in and was told my room wasn't ready. I was told it could be ready by 3 (check-in time) or sometime after and I would get a text whenever my room became available. It seems many others ..."

Reviewed on Sep. 21, 2024

Hyatt Regency Milwaukee
Four Points by Sheraton Milwaukee North Shore
Four Points by Sheraton Milwaukee North Shore
3 out of 5
8900 N Kildeer Ct, Milwaukee, WI
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Oct. 17 to Oct. 18
CA $126
CA $146 total
includes taxes & fees
Oct 17 - Oct 18
8/10 Very Good! (873 reviews)
Very pet friendly
"The staff was very friendly & helpful. The room & hotel was clean. But I got the feeling they were being pretty frugal. No blowdryer (that I could find) in the room, no coffee in the lobby, one trash can in the room. This may sound petty, but we travel quite a bit & it's these little things that ..."

Reviewed on Sep. 8, 2024

Four Points by Sheraton Milwaukee North Shore
See all 954 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

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Family Vacations

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Frequently asked questions

How much does a Jackson vacation package cost?
Customize your Jackson vacation package from just CA $787. Choose from any combination of flights, hotels and rental cars to pull together the trip you’ve been dreaming about. Don’t forget to add on a few activities!
How do I get a cheap travel package to Jackson?
Creating your own Jackson vacation package with Expedia is a smart way to save. We have access to more than 550 airlines and 1,000,000 hotels around the globe. With such an awesome range to choose from, you’ll have no difficulty putting together your next dream getaway.
Where should I stay in Jackson?
If you’ll be visiting Washington County Fair Grounds, maximize your time sightseeing and find someplace to stay close by. It’s one of the top attractions in this area.
What are the top hotels in Jackson?
Comfort Inn & Suites Jackson - West Bend is one of Jackson’s leading hotels. Reserve a room here and you can snooze soundly knowing you’re in good hands.
How far in advance should I book my Jackson vacation?
To score discount prices, book ASAP. Airlines usually release flights, along with some of the lowest fares, around 12 months prior to departure. Hotels, car rental and activities should also be booked early to avoid disappointment. If you’re in need of a last-minute getaway in Jackson, there are always lots of great deals to be had on Expedia. Book your escape today!
What does an Expedia Jackson travel package include?
Expedia has everything you need to plan your Jackson escape, but what goes into your package is entirely up to you. Pick from any combination of hotels, flights and rental cars. In search of some activities or tours to keep you entertained? Once you’ve made your booking, you can add them on too. No matter your budget, there’s a vacation package to match your needs.
What should I know before booking a Jackson travel package?
You’ll score great savings when you combine your flights, hotels and rental cars into a travel package. Not only that, booking everything in one spot makes trip planning easier. So why waste your money or time? Whether you’re putting together a fancy romantic getaway or a low-cost family break, have a look at our vacation packages today.
Can I choose my airline with a Jackson Expedia vacation package?
With a vacation package, you’re in control. Whether you’d prefer to fly to Jackson in economy or business class, simply select from the available airline options. Expedia has access to over 550 airline partners across the world.
If I'm not able to travel, can I cancel my Jackson vacation package?
Because we understand life is full of surprises, the answer is yes. For more information, check out our Customer Service Portal. But generally speaking, if you’ve booked your Jackson vacation package in the last 24 hours, you may be able to change or cancel it free of charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.