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Riley Vacation Rentals

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Riley vacation rentals

A covered outdoor area with a wooden deck, a sofa, a table, and chairs.

1. A Room with a View

A Room with a View
Verona
9.0 out of 10, Wonderful, (54 reviews)
"Beautiful view and pet friendly!"
United States
Ashley J.
$118 nightly
The price is $125
Oct 5 - Oct 6
Total with taxes and fees
A Room with a View
A bedroom with a vanity, a large mirror, a bed, and a nightstand with a lamp.

2. 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
9.8 out of 10, Exceptional, (31 reviews)
"A very unique place in a fantastic location! Little touches made our stay wonderful."
United States
Mike L.
$215 nightly
The price is $244
Oct 1 - Oct 2
Total with taxes and fees
The EarthHouse ~ Wall-to-wall unique style, Luxury Linens and Amazing Comfort
An outdoor patio with a brick grill and seating area.

3. King Suite | Free Breakfast. Pool and Hot Tub

King Suite | Free Breakfast. Pool and Hot Tub
Middleton
8.0 out of 10, Very good, (6 reviews)
"Great place for a stay."
United States
Andy D.
$157 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
King Suite | Free Breakfast. Pool and Hot Tub
A spacious living area with a wooden floor, a round mirror on the wall, and a dark-colored sofa.

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

Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
Middleton
10.0 out of 10, Exceptional, (16 reviews)
"Beautiful place, great stay."
United States
Thomas D.
$249 nightly
The price is $275
Oct 25 - Oct 26
Total with taxes and fees
Pet Friendly Fully Furnished Modern 1-Bedroom Oasis with Private Outdoor Retreat
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

5. Pool with Slide. Great for Business Travelers!

Pool with Slide. Great for Business Travelers!
Fitchburg
$170 nightly
The price is $193
Oct 4 - Oct 5
Total with taxes and fees
Pool with Slide. Great for Business Travelers!
A modern interior with a brown sofa, a round marble coffee table, and a decorative vase with flowers.

6. The Dylin

The Dylin
4.0 star property
Downtown Madison
9.4 out of 10, Exceptional, (188 reviews)
"The Dylan was a great location for us and we were very pleased with the garage parking, new modern finishes and the communication of the host. The unit had everything we needed for a super comfortable stay including a full kitchen and washer/dryer. No wasted space. Good arrangement in this two bedroom unit for 2 couples. Would stay here again and recommend."
United States
Debbie
$131 nightly
The price is $151
Oct 28 - Oct 29
Total with taxes and fees
The Dylin
A modern living room with a sofa, coffee table, and dining area.

7. Historic Luxury 2-bedroom apartment in Cross Plains, WI

Historic Luxury 2-bedroom apartment in Cross Plains, WI
Cross Plains
$346 nightly
The price is $393
Sep 29 - Sep 30
Total with taxes and fees
Historic Luxury 2-bedroom apartment in Cross Plains, WI
A hotel lobby with a fireplace, a reception desk, and shelves stocked with snacks.

8. 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
$190 nightly
The price is $215
Oct 11 - Oct 12
Total with taxes and fees
King Suite. Free Breakfast. Pool with a Slide. Close to Olbrich Botanical Gardens!
A spacious living room with a fireplace, comfortable seating, and a television mounted above it.

9. 3BR/3BA Home | Dual Living Spaces

3BR/3BA Home | Dual Living Spaces
Fitchburg
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful place with lots of room. "
United States
Brenda B.
$702 nightly
The price is $796
Oct 5 - Oct 6
Total with taxes and fees
3BR/3BA Home | Dual Living Spaces
A bedroom with a bed, a dresser, a mirror, a window with curtains, a chandelier, and a dining area visible through an open door.

10. Charming Downtown Two Bedroom w/ Fireplace

Charming Downtown Two Bedroom w/ Fireplace
New Glarus
10.0 out of 10, Exceptional, (26 reviews)
"Amazing location, nicely furnished and cozy!"
United States
Heather & Nick V.
$254 nightly
The price is $281
Oct 27 - Oct 28
Total with taxes and fees
Charming Downtown Two Bedroom w/ Fireplace
A covered patio with outdoor furniture, a view of a red barn, and a grassy field.

11. Escape to tranquility – your countryside haven, and at times with a horse or two

Escape to tranquility – your countryside haven, and at times with a horse or two
Dane
10.0 out of 10, Exceptional, (3 reviews)
"Feeding the horses was so fun and the scenery is very picturesque. Wonderful place to stay!"
United States
Katelyn F.
$218 nightly
The price is $241
Oct 11 - Oct 12
Total with taxes and fees
Escape to tranquility – your countryside haven, and at times with a horse or two
A wooden dock leading to a house with a balcony, surrounded by trees and a body of water.

12. 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, (56 reviews)
"Great little lake house, close to downtown Madison. "
United States
LiHsin C.
$413 nightly
The price is $468
Oct 12 - Oct 13
Total with taxes and fees
Madison Lakefront Oasis in the Heart of Madison - Central, Minutes to Downtown!
A spacious kitchen with wooden beams, a central island, and a dining area with a blue sofa and chairs.

13. Doty ★ Walk to Everything -Hotel Quality- Downtown

Doty ★ Walk to Everything -Hotel Quality- Downtown
Downtown Madison
9.8 out of 10, Exceptional, (45 reviews)
"Great place!"
United States
Robert F.
$458 nightly
The price is $529
Oct 8 - Oct 9
Total with taxes and fees
Doty ★ Walk to Everything -Hotel Quality- 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

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

10/10 Excellent
"Great experience, just a little bit walk to U of W."
Yunfei 1-night trip
Posted 1 hour ago
The Madison Concourse Hotel and Governor's Club

Find out more about Riley

Everything you need to know about Riley vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Riley vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Riley vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Riley vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Riley. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Riley in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Riley rentals

At Expedia, we put the best Riley vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Riley rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Riley vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Riley. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Pet FriendlyHot tub space to relax 10min from Madison, Epic, MilitaryRidgeTrail: Visitors like this Riley vacation home rental. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a private yard, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 Reddan Soccer Park.

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.