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.
Best Western Dodgeville Inn & Suites
Price was CA $1,236, price is now CA $1,161 per person
CA $1,161
per person
Sep 13 - Sep 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Madison (MSN)
8.4/10 Very good! (671 reviews)
Kids loved the indoor/outdoor pool. The help was pleasant and helpful. The rooms were clean and large. The breakfast was standard hotel fare. Wish some hotels could upgrade this but they are all the same.
Reviewed on Jun 13, 2026
Holiday Inn Express Wisconsin Dells by IHG
Price was CA $1,841, price is now CA $1,704 per person
CA $1,704
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
8.8/10 Excellent! (1,010 reviews)
The room was nice &clean, staff were friendly,like location of our hotel, breakfast was good.
Reviewed on Jun 17, 2026
avid Hotel Wisconsin Dells – Lake Delton by IHG
Price was CA $1,713, price is now CA $1,593 per person
CA $1,593
per person
Jul 25 - Aug 1
found 6 hours ago
Roundtrip non-stop flight included
Winnipeg (YWG) to Madison (MSN)
9.4/10 Exceptional! (627 reviews)
I like this hotel. The amenities were good. I would have given it 5 stars except the bed in my room was squeaking when I get on and off.
Reviewed on Jun 21, 2026
Middleton Hotel Deals
Hilton Garden Inn Madison West/Middleton
1801 Deming Way Middleton WI
Fully refundableReserve now, pay when you stay
The price is CA $123 per night from Jun 28 to Jun 29
CA $123
CA $140 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (1,006 reviews)
"Clean room, great staff, great location!"
Reviewed on Jun 22, 2026
Country Inn & Suites by Radisson, Middleton - Madison West
2212 Deming Way Middleton WI
Fully refundable
The price is CA $123 per night from Jul 13 to Jul 14
CA $123
CA $140 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
"The rooms were decent but the hallways and one of the rooms we booked smelled like cigarettes. So for that reason, I can't give it 5 stars."
Reviewed on Jun 22, 2026
Holiday Inn Express & Suites Madison West - Middleton by IHG
8353 MURPHY DRIVE Middleton WI
Fully refundable
The price is CA $125 per night from Jul 5 to Jul 6
CA $125
CA $141 total
Jul 5 - Jul 6
includes taxes & fees
9.6/10 Exceptional! (726 reviews)
"Great good price place to stay outside of Madison."
Reviewed on Jun 23, 2026
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.
What to do in Middleton
Murmurs of Mourning & Murder: Madison Ghost Tour
CA $44
per adult
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
CA $14
per traveller
100% of travellers recommend
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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.
