Riley Vacations from $439
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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!
The Latest Riley vacation packages
Price found within the past 48 hours. Click for updated prices.
Madison Marriott South
$646
per person
Sep 16 - Sep 19
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to Madison (MSN)
9/10 Wonderful! (589 reviews)
Stayed two nights and had a wonderful experience. Clean and quiet. Would go back again when we are back in Madison.
Reviewed on Aug 13, 2026
Club Wyndham Glacier Canyon
$567
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Denver (DEN) to Madison (MSN)
9/10 Wonderful! (426 reviews)
My husband and I stayed with Club Wyndham for the first time at the Wilderness Glacier Canyon Lodge. Our four night stay was nothing but pure bliss, and we definitely plan on coming back! After check-in we were told about some of the benefits Wyndham timeshares had to offer and were asked if we would like to attend their tour, but we were not interested at the time to which they had no problem with and told us to enjoy our stay!
The Wilderness resort brings back much nostalgia because I used to visit there all the time with my family as a child. Now, my husband and I want to continue the tradition with our family. This place has everything the whole family could want on a vacation. From the waterparks to the arcades to food, they have it all. We have already made so many great memories there, and we highly recommend going! Just remember they do get very busy during peak season, so if you’re looking for a more laid back version of the Wilderness, we recommend going during their off-season! Also, be sure to check out the downtown (our favorite restaurant is the Dell Bar) as well as Devil’s Lake State Park!
Reviewed on Jun 3, 2026
What to do in Riley
Murmurs of Mourning & Murder: Madison Ghost Tour
$26
per adult
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
$10
per traveler
100% of travellers recommend
Riley Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
$161 total
Sep 6 - Sep 7
Total with taxes and fees
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
$58 nightly
$67 total
Aug 23 - Aug 24
Total with taxes and fees
8/10 Very Good! (1,424 reviews)
"Upon arrival I was disappointed that they didn't have a room for me on the first floor as I requested when I made the reservation a week prior. However, the front desk attendant was very kind and friendly so I immediately got over my disappointment her name is Cat, she was delightful! The pool is ..."
Reviewed on Aug 13, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
$126 nightly
$146 total
Aug 31 - Sep 1
Total with taxes and 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.
Find the Best Riley Vacation Packages
Riley Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Dane County Regional Airport (MSN) |
Top Sights | Wisconsin Brewing Company, Firemans Beach and Reddan Soccer Park |
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Frequently asked questions
How much does a Riley vacation package cost?
You'll find cheap prices from $439 on Expedia for your Riley escape. However, factors like the length of stay, the season and your choice of hotel will influence how much your vacation to Riley costs.
What are the cheapest months to go to Riley?
You're likely to find reduced prices and better availability in November, December and January. Explore our cheap Riley vacation packages and you could get some excellent off-season deals.
How many days is enough for Riley?
Usually, a handful of days is enough to tick off the major sights during your Riley vacation. However, if you'd like to have some time to unwind or take day trips, think about extending your itinerary.
How to find the best Riley package deals?
Bagging a cheap Riley package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add some filters and see what's available. You can personalize your search by "Amenities," "Property type," "Traveler experience" and more. Order the results by "Price: low to high" to view the most economical Riley package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider traveling on a weekday, when prices are typically lower.
Is it cheaper to book a Riley vacation as a package?
You can enjoy significant savings on your next Riley retreat by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see the best hotel prices and airfares. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Riley?
Enjoy amazing discounts by reserving your flights early with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Riley getaway.
Does Expedia offer Book Now, Pay Later Riley vacation packages?
Set off on your dream escape to Riley with our Book Now, Pay Later vacations. There's no need to save up or wait for your next paycheck — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans let you split the cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's a breeze to budget for your trip and snap up cheap deals before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
