Riley Vacation Packages
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Your Riley Vacation
With everything organized before you go, our Riley vacation packages mean you can concentrate on having fun. Whether you base yourself in the neighborhood of Shorewood Hills, which is good for golfing, or another part of town, this lively city offers plenty of discoveries. Love to explore your surroundings? University Ridge Golf Course, Reddan Soccer Park and Verona Ice Arena are three of the top places to visit during a trip to Riley. Stop daydreaming and start traveling. Browse the many options on Expedia today and put your Riley vacation plans into motion!
Top Riley Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Courtyard by Marriott Madison East
Price was CA $535, price is now CA $503 per person
CA $503
per person
Jul 12 - Jul 14
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Madison (MSN)
9/10 Wonderful! (669 reviews)
Didn't like that you had to pay extra for breakfast. Our phone in our room was not operable. The firepit was out of propane for who knows how long, at least two nights and maintenance new about it. I mean really, it would take not even five minutes to change out the tank. Last, I prefer not having to physically check out.
Reviewed on Jun 2, 2026
1810 Emerson House Bed & Breakfast - Adults Only
Price was CA $1,437, price is now CA $1,163 per person
CA $1,163
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Madison (MSN)
9.6/10 Exceptional! (13 reviews)
Simply the BEST stay! Tony and Beth are the kindest hosts! The space is cozy and intimate; perfect for special occasions. My husband and I have had the privilege of staying here 3 times, and this will always be one of our favorite spots for a getaway! We highly recommend this gem!
Reviewed on Mar 22, 2026
Baymont by Wyndham Janesville
Price was CA $769, price is now CA $648 per person
CA $648
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Madison (MSN)
8/10 Very Good! (1,002 reviews)
The staff were accommodating we had a family emergency and had to shorten our stay. They worked with us to cancel part of our reservation without charging us cancelation fees.
The only thing that we were disappointed with was that breakfast ended at 9 am, wishing it went to 10 am.
Reviewed on Jun 8, 2026
Motel 6 Janesville, WI
Price was CA $709, price is now CA $663 per person
CA $663
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Madison (MSN)
7/10 Good! (936 reviews)
I first stayed here 40 years ago. Janesville has truly grown. For rest it was just fine. Probably a little dated. But all in all just fine. Staff was incredibly friendly.
Reviewed on Jun 9, 2026
Riley Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Jun 14 to Jun 15
CA $165
CA $190 total
Jun 14 - Jun 15
includes taxes & fees
9.4/10 Exceptional! (3,864 reviews)
"It would be really nice if they had complimentary coffee and water, like most of the hotels that I stay in do."
Reviewed on Jun 11, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jun 28 to Jun 29
CA $167
CA $193 total
Jun 28 - Jun 29
includes taxes & fees
9.2/10 Wonderful! (1,011 reviews)
"Great service as usual!! Clean rooms and a great breakfast!!"
Reviewed on Jun 11, 2026
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $148 per night from Jun 25 to Jun 26
CA $148
CA $170 total
Jun 25 - Jun 26
includes taxes & fees
9.4/10 Exceptional! (1,030 reviews)
"Nice place to stay while traveling."
Reviewed on Jun 10, 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 Riley
Murmurs of Mourning & Murder: Madison Ghost Tour
CA $44
per adult
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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.
