Middleton Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
Valued Stay Madison
Price was CA $461, price is now CA $384 per person
CA $384
per person
Oct 20 - Oct 24
found 20 hours ago
Roundtrip flight included
Calgary (YYC) to Madison (MSN)
6.2/10 (956 reviews)
For the budget minded traveler this stay was good. The room.was clean and comfortable. The staff was friendly and there many breakfast options. I felt safe staying here and parking was well lit.
Reviewed on Sep 7, 2025
MainStay Suites Madison - Monona
Price was CA $603, price is now CA $513 per person
CA $513
per person
Oct 20 - Oct 24
found 20 hours ago
Roundtrip flight included
Calgary (YYC) to Madison (MSN)
9.4/10 Exceptional! (419 reviews)
The room was fine. There was no shampoo or conditioner and when we called the desk, they would not deliver it. The fitness center is small but adequate but very hot. Waited on line at the front desk for 10 minutes until someone came who could turn on the fan.
Reviewed on Sep 5, 2025
Middleton Hotel Deals
Country Inn & Suites by Radisson, Madison West, WI
2212 Deming Way, Middleton, WI
Fully refundable
The price is CA $117 per night from Sep 13 to Sep 14
CA $117
CA $132 total
Sep 13 - Sep 14
includes taxes & fees
Holiday Inn Express & Suites Madison West - Middleton by IHG
8353 MURPHY DRIVE, Middleton, WI
Fully refundable
The price is CA $126 per night from Sep 28 to Sep 29
CA $126
CA $143 total
Sep 28 - Sep 29
includes taxes & fees
Fairfield Inn & Suites by Marriott Madison West/Middleton
8212 Greenway Blvd, Middleton, WI
The price is CA $117 per night from Sep 21 to Sep 22
CA $117
CA $132 total
Sep 21 - Sep 22
includes taxes & fees
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.
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
