Middleton Vacation Packages

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Your Middleton Vacation

From its welcoming locals to its family-friendly attractions and beyond, there's loads to love about Middleton. Discover the delights of this awesome city with a Middleton vacation package that's made for you. If a sightseeing tour is on the agenda during your trip to Middleton, visit well-known attractions like University of Wisconsin-Madison, Camp Randall Stadium and Henry Vilas Zoo. That dream Middleton vacation is a couple of clicks away. Browse accommodations, flights and more on Expedia for a getaway that's tailored just for you.

Top Middleton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Madison Downtown

DoubleTree by Hilton Madison Downtown

4 out of 5
Downtown Madison
per person
Oct 3 - Oct 5
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Madison (MSN)
9.6/10 Exceptional! (1,005 reviews)
Staff are excellent!

Reviewed on Aug. 15, 2025

The Dylin

The Dylin

4 out of 5
Tenney-Lapham
per person
Oct 2 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Madison (MSN)
9.2/10 Wonderful! (82 reviews)
Nice, clean, well-equipped and well-decorated rooms.

Reviewed on Jul. 27, 2025

Hyatt Place Madison Downtown

Hyatt Place Madison Downtown

3 out of 5
Downtown Madison
per person
Oct 2 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Madison (MSN)
9.2/10 Wonderful! (1,006 reviews)
We liked the property and convenience being downtown. We did not like the tiny bathroom getting into the bathroom with the tiny toilet. The large shower was nice though. Otherwise the suite was very nice.

Reviewed on Aug. 17, 2025

Graduate by Hilton Madison

Graduate by Hilton Madison

4 out of 5
Downtown Madison
per person
Oct 2 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Madison (MSN)
9/10 Wonderful! (1,000 reviews)
Clean facilities, friendly staff, quiet, great location.

Reviewed on Aug. 3, 2025

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
Downtown Madison
per person
Oct 2 - Oct 4
found 13 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Madison (MSN)
9.4/10 Exceptional! (2,950 reviews)
walking distance from the Capitol building, restaurants, and bars.

Reviewed on Aug. 17, 2025

Ready to book your vacation to Middleton?

 

Choose your dates

Middleton Hotel Deals

Country Inn & Suites by Radisson, Madison West, WI

Country Inn & Suites by Radisson, Madison West, WI

2.5 out of 5
2212 Deming Way, Middleton, WI
Fully refundable
The price is CA $116 per night from Aug 31 to Sep 1
CA $116
CA $132 total
Aug 31 - Sep 1
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Very good location"

Reviewed on Aug. 15, 2025

Country Inn & Suites by Radisson, Madison West, WI
Fairfield Inn & Suites by Marriott Madison West/Middleton

Fairfield Inn & Suites by Marriott Madison West/Middleton

2.5 out of 5
8212 Greenway Blvd, Middleton, WI
Fully refundableReserve now, pay when you stay
The price is CA $116 per night from Aug 31 to Sep 1
CA $116
CA $132 total
Aug 31 - Sep 1
includes taxes & fees
9/10 Wonderful! (876 reviews)
"Clean, convenient, good breakfast."

Reviewed on Aug. 12, 2025

Fairfield Inn & Suites by Marriott Madison West/Middleton
Holiday Inn Express And Suites Madison West - Middleton by IHG

Holiday Inn Express And Suites Madison West - Middleton by IHG

2.5 out of 5
8353 MURPHY DRIVE, Middleton, WI
Fully refundable
The price is CA $140 per night from Aug 24 to Aug 25
CA $140
CA $158 total
Aug 24 - Aug 25
includes taxes & fees
9.6/10 Exceptional! (552 reviews)
"The property is fine and rooms are comfortable. Breakfast was good and had decent variety. For being a pretty new building, the AC is tremendously noisy, to the point that we had to turn it off during the night to allow us to sleep. Indoor pool was very cold, not suited for children in my ..."

Reviewed on Aug. 16, 2025

Holiday Inn Express And Suites Madison West - Middleton by IHG
See all 431 properties in Middleton
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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Frequently asked questions

How much does a Middleton vacation package cost?
Offering great value package deals from CA $971 on Expedia, you'll be surprised at how little a vacation to Middleton costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Middleton?
If you'd like to snag a cheap Middleton vacation package, consider visiting in December, January and February. You're likely to find better rates on accommodations and flights during these months — ideal for a budget-friendly getaway.
How many days is enough for Middleton?
With around 2 days, you'll have plenty of time to visit popular neighbourhoods such as Regent and Spring Harbour during your Middleton vacation. Make sure to also add Kohl Centre and West Towne Mall to your must-do list. Searching for more adventures? Consider venturing outside of Middleton on tours and day trips.
How to find the best Middleton package deals?
Begin your search for a Middleton package deal by entering your travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the perfect Middleton package deal right away, just change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middleton escape underway.
Is it cheaper to book a Middleton vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the freedom to create a customized Middleton vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Middleton?
Land incredible discounts by reserving your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middleton trip.
How to plan a trip to Middleton?

  1. Pick your dates: What you plan to do in Middleton and your favourite season will help you decide when to travel.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Middleton. Then, pick a hotel that suits your budget, whether that's an economical option or a lavish retreat.
  3. Decide how long to go for: Now that you're more familiar with Middleton, you can figure out the ideal length of your vacation. Put together a draft plan and allocate enough time for all the things you want to do.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Middleton vacation package that brings all your bookings together.

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