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

Aparthotel in Tenney-Lapham

The Dylin by Mint House
4.0 star property
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
Exterior
ONE OF A KIND vacation rental with a view

Vacation Home in Madison

ONE OF A KIND vacation rental with a view
10.0 out of 10, Exceptional, (147)
"This is a unique home that is super clean and had everything needed to cook, entertain (we played games & watched football) and accommodate any family. The location was close to downtown, the interstate, and airport. Plenty of restaurants were nearby as well. We thoroughly enjoyed our stay and would absolutely stay again. "
United States
Connie C.
ONE OF A KIND vacation rental with a view
Indoor pool, a heated pool
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!

Vacation Home in Arena

Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
9.8 out of 10, Exceptional, (7)
"Perfect spot for a family getaway"
United States
Steve M.
Barn! Pool w/ Rock Climbing Wall! Indoor BBall/Pickleball Court + Playground!
Smart TV, fireplace, DVD player, books
Conveniently Located just off University Avenue on Madison's West Side

Vacation Home in Spring Harbor

Conveniently Located just off University Avenue on Madison's West Side
10.0 out of 10, Exceptional, (131)
"It was great!"
United States
Guitar string S.
Conveniently Located just off University Avenue on Madison's West Side
Smart TV, fireplace, video games, DVD player
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail

Vacation Home in Verona

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
9.6 out of 10, Exceptional, (69)
"Beautiful location, nice spacious and clean spot. We had a great time. "
United States
Sarah B.
Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail
Terrace/patio
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access

Vacation Home in Faircrest

Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
10.0 out of 10, Exceptional, (120)
"Scenic property, super zen, lovely hosts!"
United States
Christina C.
Hot Tub with a View, Private Modern Garden Level Apartment, Conservancy Access
Lobby
Pool with Slide. Great for Business Travelers!

Apartment in Fitchburg

Pool with Slide. Great for Business Travelers!
The price is ￥19,088
￥25,068 total
includes taxes & fees
Dec 18 - Dec 19
Pool with Slide. Great for Business Travelers!
Dining
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym

Vacation Home in Arena

Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
9.6 out of 10, Exceptional, (22)
"Barn was beautiful, clean & fun amenities."
United States
Kerry S.
Barnhouse! Mini Golf, Slide, Theater, Arcade/Games, Pool/Hot Tub/Sauna, Home Gym
Exterior
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.

Vacation Home in McFarland

Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
10.0 out of 10, Exceptional, (13)
"Nice stay"
United States
Rebecca S.
Charming 4 Bed, 2.5 Bath home minutes from Madison perfect for any occasion.
Fridge, microwave, oven, stovetop
Madison & ~UW~-Madison Area Lakefront Home

Cottage in McFarland

Madison & ~UW~-Madison Area Lakefront Home
10.0 out of 10, Exceptional, (202)
"What a lovely place to spend a few days with family! There was so much to do within a short distance but we loved being able to just chill on the water. We had a wonderful stay and can’t wait to visit again. Would highly recommend! "
United States
Jody G.
Madison & ~UW~-Madison Area Lakefront Home
Interior
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat

Apartment in Middleton

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
2.0 star property
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
Fridge, microwave, oven, stovetop
Doty ★ Walk to Everything -Hotel Quality- Downtown

Vacation Home in Downtown Madison

Doty ★ Walk to Everything -Hotel Quality- Downtown
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
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort

Vacation Home in Mount Horeb

The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
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
Exterior
On the Yahara River, access to Madison Lakes

Vacation Home in Monona

On the Yahara River, access to Madison Lakes
10.0 out of 10, Exceptional, (52)
"Great stay - very relaxing!"
United States
Karen S.
On the Yahara River, access to Madison Lakes
Fridge, microwave, oven, stovetop
Clean and spacioius flat in great location near Epic and downtown Verona!

Apartment in Verona

Clean and spacioius flat in great location near Epic and downtown Verona!
10.0 out of 10, Exceptional, (30)
"good location and value for the money. We were pleased to bring our dog with us!"
United States
audrey w.
Clean and spacioius flat in great location near Epic and downtown Verona!
Fridge, microwave, oven, stovetop
Paoli Den - Renovated Flat!

Vacation Home in Verona

Paoli Den - Renovated Flat!
9.8 out of 10, Exceptional, (31)
"Charming place, great communication with owners!"
United States
Ed D.
Paoli Den - Renovated Flat!
Fridge, microwave, oven, stovetop
Cozy Cabin in The Driftless

Vacation Home in Cross Plains

Cozy Cabin in The Driftless
9.2 out of 10, Wonderful, (63)
"The cabin was clean and well supplied. It was great for our long weekend getaway"
United States
rose b.
Cozy Cabin in The Driftless
Fridge, microwave, oven, stovetop
Luxurious Country Retreat

Vacation Home in Mount Horeb

Luxurious Country Retreat
9.8 out of 10, Exceptional, (16)
"Overall, we thoroughly enjoyed our stay. Property is large and has many wonderful features for hosting many other guests. Host was very prompt with communication responses, which we greatly appreciated. Would definitely stay again! "
United States
Amanda R.
Luxurious Country Retreat
1 bedroom
One Bedroom King with views of Lake Monona in the heart of downtown.

Vacation Home in Downtown Madison

One Bedroom King with views of Lake Monona in the heart of downtown.
2.0 star property
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.
Exterior
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!

Vacation Home in Monona

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