Riley Vacations from $218

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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.
Motel 6 Janesville, WI

Motel 6 Janesville, WI

2 out of 5
Price was $250, price is now $218 per person
$218
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Madison (MSN)
7/10 Good! (827 reviews)
I had to try three rooms before I got a good one first one had not even been cleaned second one the heater didn't work the third times a charm. It was average pretty cheap hotel the concierge was very helpful and apologetic

Reviewed on Dec 16, 2025

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

Bluegreen Vacations Christmas Mountain Village, an Ascend Collection Resort

3 out of 5
Price was $527, price is now $408 per person
$408
per person
Mar 6 - Mar 9
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
8.4/10 Very Good! (122 reviews)
didn't ski or use pool but setting was very good and staff friendly. liked upstairs downstairs bedrooms

Reviewed on Dec 27, 2025

Madison Marriott South

Madison Marriott South

3.5 out of 5
Price was $925, price is now $800 per person
$800
per person
Mar 28 - Mar 31
found 12 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to Madison (MSN)
9/10 Wonderful! (524 reviews)
Great location along the lake and trails

Reviewed on Aug 10, 2025

The Speckled Hen Inn B&B

The Speckled Hen Inn B&B

4 out of 5
Price was $690, price is now $604 per person
$604
per person
Mar 5 - Mar 7
found 18 hours ago
Roundtrip non-stop flight included
Knoxville (TYS) to Madison (MSN)
9.8/10 Exceptional! (9 reviews)
Valued Stay Sun Prairie

Valued Stay Sun Prairie

2.5 out of 5
Price was $296, price is now $260 per person
$260
per person
Mar 6 - Mar 9
found 15 hours ago
Roundtrip flight included
Chicago (ORD) to Madison (MSN)
7/10 Good! (534 reviews)
Parking was safe and easy parking.we got a king size bed

Reviewed on Dec 29, 2025

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Discover the most popular places to visit in Riley

Reddan Soccer Park

4/5(2 reviews)

Enjoy a trip to Reddan Soccer Park and popular activities like biking in Verona. Stroll along the lakeside or attend a sporting event in this family-friendly area.

Reddan Soccer Park

Verona Ice Arena

3/5(2 reviews)

Enjoy a trip to Verona Ice Arena and popular activities like biking in Verona. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Verona Ice Arena

Wisconsin Brewing Company

4/5(7 reviews)

Enjoy a trip to Wisconsin Brewing Company and popular activities like biking in Verona. Amble around this family-friendly area's lakeside and enjoy its top-notch restaurants.

Wisconsin Brewing Company

What to do in Riley

Haunted Madison Capitol Building on Madison Ghosts Haunted Walking Tour

Murmurs of Mourning & Murder: Madison Ghost Tour

$32
per adult
Murmurs of Mourning & Murder: Madison Ghost Tour
Trolley Pub Public Tour

Trolley Pub Public Tour

$45
per adult
Trolley Pub Public Tour
See all activities in Riley

Riley Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $161 total per night from Jan 18 to Jan 19
$161 total
Jan 18 - Jan 19
Total with taxes and fees
9.4/10 Exceptional! (3,427 reviews)
This was a great place to stay! The room was clean & spacious. The location is close to everything downtown Madison. The weather wasn’t great & the hotel has a shuttle service that will take you most anywhere you want to go. The bar & bartender Dallas were awesome! Dallas gave us great recommendations ...

Reviewed on Jan 4, 2026

The Madison Concourse Hotel and Governor's Club
Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

2.5 out of 5
483 Commerce Dr Madison WI
Fully refundableReserve now, pay when you stay
$73 nightly
The price is $84 total per night from Jan 19 to Jan 20
$84 total
Jan 19 - Jan 20
Total with taxes and fees
9/10 Wonderful! (1,000 reviews)
The front dest staff were exceptional, always a smiling face and a welcoming greeting. The room was clean and comfortable. I am confused about the billing. I was charged, but also credited for more than the charge of the room.

Reviewed on Jan 3, 2026

Hampton Inn & Suites Madison-West
DoubleTree by Hilton Madison East

DoubleTree by Hilton Madison East

4 out of 5
4402 E Washington Ave Madison WI
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $122 total per night from Jan 13 to Jan 14
$122 total
Jan 13 - Jan 14
Total with taxes and fees
9.2/10 Wonderful! (1,002 reviews)
Great amenities and really friendly staff.

Reviewed on Jan 9, 2026

DoubleTree by Hilton Madison East
See all 337 properties in Riley
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 $218 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.