Riley Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Our top choices for Riley vacation rentals

Interior entrance
The Dylin by Mint House

The Dylin by Mint House

The Dylin by Mint House
4.0 star property
Tenney-Lapham
9.4 out of 10, Exceptional, (121)
"Great location and very comfortable stay. Love the extra space to hang out."
United States
Brian
The price is ￥17,179
￥19,841 total
includes taxes & fees
Dec 23 - Dec 24
The Dylin by Mint House
Private kitchen
One Bedroom Queen in the heart of downtown.

One Bedroom Queen in the heart of downtown.

One Bedroom Queen in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay and the close location to the capital. Great modern style and very functional "
United States
Alexandrines H.
The price is ￥26,278
￥34,662 total
includes taxes & fees
Dec 23 - Dec 24
One Bedroom Queen in the heart of downtown.
Outdoor dining
Sugar River Suite - Your Sweet Escape in the Heart of it All!

Sugar River Suite - Your Sweet Escape in the Heart of it All!

Sugar River Suite - Your Sweet Escape in the Heart of it All!
New Glarus
10.0 out of 10, Exceptional, (20)
"Super clean & right in the middle of town. Great place for a girls getaway weekend!"
United States
Rachel I.
The price is ￥17,521
￥27,966 total
includes taxes & fees
Dec 15 - Dec 16
Sugar River Suite - Your Sweet Escape in the Heart of it All!
Lobby
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!

King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Fitchburg
The price is ￥22,291
￥28,864 total
includes taxes & fees
Dec 14 - Dec 15
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
Lobby
Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
The price is ￥19,088
￥25,068 total
includes taxes & fees
Dec 18 - Dec 19
Pool with Slide. Great for Business Travelers!
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (36)
"Beautiful apartment with all we needed for a comfortable family July 4th weekend away!! "
United States
Mindi Z.
The price is ￥26,491
￥44,628 total
includes taxes & fees
Dec 14 - Dec 15
Doty ★ Walk to Everything -Hotel Quality- Downtown
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Monona
9.8 out of 10, Exceptional, (47)
"We had a great time on our weekend trip to Madison. Location was super quick to get to downtown, house was clean, and we really enjoyed taking the canoe out on the lakes to explore."
United States
Molly S.
The price is ￥37,112
￥77,417 total
includes taxes & fees
Dec 14 - Dec 15
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
Fridge, microwave, oven, stovetop
Cozy Winter Haven | Minutes to Downtown

Cozy Winter Haven | Minutes to Downtown

Cozy Winter Haven | Minutes to Downtown
Fitchburg
10.0 out of 10, Exceptional, (19)
"Property was generally clean, spacious and had all the amenities that our family needed.An enjoyable stay at a nice property!"
United States
Kim & Jeff T.
The price is ￥50,292
￥121,931 total
includes taxes & fees
Dec 14 - Dec 15
Cozy Winter Haven | Minutes to Downtown
Outdoor dining
Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!

Enjoy Nature with Full Comfort!
Verona
9.2 out of 10, Wonderful, (37)
"Well-appointed, very clean space on a stunning property! Easy check-in. Everything we needed. Good communication with the host. We hope to return!"
United States
Thea S.
The price is ￥12,595
￥19,850 total
includes taxes & fees
Dec 14 - Dec 15
Enjoy Nature with Full Comfort!
Exterior
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Mount Horeb
10.0 out of 10, Exceptional, (19)
"Very clean and comfortable and a great location within walking distance to downtown."
United States
Holly
The price is ￥17,131
￥30,117 total
includes taxes & fees
Dec 28 - Dec 29
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
Interior
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
2.0 star property
Middleton
10.0 out of 10, Exceptional, (2)
"We had a fantastic stay at this property, and it truly exceeded our expectations. The location is excellent—perfectly situated with convenient access to both the east and west sides of Madison, making it easy to get wherever we needed to go. The owners were incredibly helpful and responsive, answering the few questions we had quickly and kindly, which made the entire experience even smoother.One of the biggest highlights for us was the private fenced-in area, which was absolutely perfect for our...
United States
Jessi P.
The price is ￥22,251
￥47,098 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Terrace/patio
King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very Good, (5)
"Great place for a stay."
United States
Andy D.
The price is ￥16,015
￥22,006 total
includes taxes & fees
Dec 14 - Dec 15
King Suite | Free Breakfast. Pool and Hot Tub
Private kitchen
Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (1)
"Convenient location for events on the Capital Square, State Street and UW-Madison Campus."
United States
Jeffrey W.
The price is ￥26,320
￥34,718 total
includes taxes & fees
Dec 25 - Dec 26
Studio Queen in the heart of downtown.
Private kitchen
One Bedroom King with Office with views of Lake Monona in the heart of downtown.

One Bedroom King with Office with views of Lake Monona in the heart of downtown.

One Bedroom King with Office with views of Lake Monona in the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (2)
"The place is beautiful and perfectly appointed with necessary equipment. Gorgeous view! Easy and convenient parking and check in. "
United States
Maggie C.
The price is ￥32,497
￥42,385 total
includes taxes & fees
Dec 21 - Dec 22
One Bedroom King with Office with views of Lake Monona in the heart of downtown.
Outdoor dining
One Bedroom King with views of the heart of downtown.

One Bedroom King with views of the heart of downtown.

One Bedroom King with views of the heart of downtown.
2.0 star property
Downtown Madison
10.0 out of 10, Exceptional, (2)
"The property was easy to check-in and very clean! It had all the amenities to feel right at home. Excellent location close to restaurants within walking distance. We had a lovely time!"
United States
Vikki T.
The price is ￥27,833
￥36,638 total
includes taxes & fees
Dec 24 - Dec 25
One Bedroom King with views of the heart of downtown.
WiFi
Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.

Studio Queen in the heart of downtown.
2.0 star property
Downtown Madison
The price is ￥24,723
￥32,328 total
includes taxes & fees
Dec 14 - Dec 15
Studio Queen in the heart of downtown.
1 bedroom
One Bedroom King with views of Lake Monona in the heart of downtown.

One Bedroom King with views of Lake Monona in the heart of downtown.

One Bedroom King with views of Lake Monona in the heart of downtown.
2.0 star property
Downtown Madison
The price is ￥29,388
￥38,254 total
includes taxes & fees
Dec 14 - Dec 15
One Bedroom King with views of Lake Monona in the heart of downtown.
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.
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Top Riley Hotel Reviews

Hampton Inn & Suites Madison-West

Hampton Inn & Suites Madison-West

10/10 Excellent
"Yes"
terrence 1-night trip
Posted 2 days ago
Hampton Inn & Suites Madison-West

Find out more about Riley

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Look no further and take a look at our great range of rental properties in Riley!

Frequently asked questions

Are there vacation rentals in Riley?

Yes, we give you a choice of vacation rentals close to popular points of interest in Riley, or you can go with a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals in Riley?

Conveniently Located just off University Avenue on Madison's West Side : Visitors like this Riley vacation home rental. It offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

What can I see and do in Riley?

Explore the area and family-friendly sights such as Verona Ice Arena, or get out into nature at a spot like Cave of The Mounds National Natural Landmark. In the larger area, you’ll find University Ridge Golf Course and Mt. Horeb Area Museum.

What are vacation rentals like in Riley?

Vacation rentals are privately owned properties you can stay in for a couple days or more in Riley. Vacation rentals feature amenities such as patios, hot tubs, and fire pits to help you enjoy your stay. If you're concerned about cleanliness, a vacation rental can offer a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great option for small groups.