Riley Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Riley
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
S$173
6 Sept - 7 Sept
includes taxes & fees
9.4/10 Exceptional! (4,111 reviews)
"Great place and so close to everything"
Reviewed on 23 Aug, 2026
Baymont by Wyndham Madison West/Middleton WI West
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
S$96
20 Sept - 21 Sept
includes taxes & fees
8/10 Very good! (1,450 reviews)
"The price was affordable and the location was convenient and easy to get to and from Verona, which was a good point. The bad point is there isn't much insulation between the rooms. The room next to us was extremely loud, we think they had friends come over and talked all night both nights. We said ..."
Reviewed on 23 Aug, 2026
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Fully refundableReserve now, pay when you stay
S$185
31 Aug - 1 Sept
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.
What to do in Riley
Madison Must-See and Must-Eat Locations with Self-Guided Audio Tour
S$13
per traveller
80% of travellers recommend
Downtown Madison Sightseeing & History with Self-Guided Audio Tour
S$13
per traveller
100% of travellers recommend
Murmurs of Mourning & Murder: Madison Ghost Tour
S$34
per adult
Frequently asked questions
How much does a Riley holiday package cost?
You'll find cheap prices 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 holiday to Riley costs.
What are the cheapest months to go to Riley?
You can generally find lower rates and better availability in January, February and November. Check out our cheap Riley holiday packages and you could get some great off-season discounts.
How many days is enough for Riley?
Usually, a handful of days is enough to go to the major sights during your Riley holiday. But if you want to have more time to rest or take day tours, 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 personalise your search by "Amenities," "Property type," "Traveller 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 travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Riley holiday as a package?
You can enjoy significant savings on your next Riley retreat by booking a tailored holiday 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 holiday 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.
How to plan a trip to Riley?
- Choose your travel dates: The things you plan to do in Riley and your preferred season can help you decide when to get away.
- Set your budget: Consider costs like flights, transportation and food when working out how much to set aside for your trip to Riley. Then, pick a hotel that fits your budget, whether that's an economical option or a more upscale retreat.
- Determine how many days away: Start by making a list of all the attractions and activities you'd like to experience in Riley. Then, estimate how long you'll need at each, along with any travel time.
- Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to choose a Riley holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
