Madison Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Rentals in Madison

Outdoor dining
Secluded Chalet near Ohiopyle and Seven Springs

Secluded Chalet near Ohiopyle and Seven Springs

Bear Rocks
10.0 out of 10, Exceptional, (1)
$243 nightly
The price is $258
Dec 8 - Dec 9
Total with taxes and fees
Secluded Chalet near Ohiopyle and Seven Springs
Fridge, microwave, oven, stovetop
Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!

Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!

Connellsville
10.0 out of 10, Exceptional, (7)
"Lovely place and thoughtfully appointed. The coffee was amazingly good!"
United States
Elizabeth K.
$170 nightly
The price is $188
Jan 7 - Jan 8, 2026
Total with taxes and fees
Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!
TV
The Light Room

The Light Room

McKeesport
9.6 out of 10, Exceptional, (4)
"The house has a very peaceful atmosphere."
United States
Susan G.
$150 nightly
The price is $170
Dec 8 - Dec 9
Total with taxes and fees
The Light Room
Property grounds
Cozy Studio with Unique Charm in Private Setting

Cozy Studio with Unique Charm in Private Setting

South Park
10.0 out of 10, Exceptional, (69)
"Everything was perfect. Will stay there next trip to see family. "
United States
Joyce P.
$163 nightly
The price is $180
Dec 9 - Dec 10
Total with taxes and fees
Cozy Studio with Unique Charm in Private Setting
Dining
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen

3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen

2.0 star property
Squirrel Hill
10.0 out of 10, Exceptional, (3)
"It was a pleasure staying there"
United States
msimchowitz
$204 nightly
The price is $230
Dec 21 - Dec 22
Total with taxes and fees
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
Dining
The Upper Room

The Upper Room

McKeesport
9.4 out of 10, Exceptional, (6)
"Great place and an awesome host!"
United States
John B.
$155 nightly
The price is $175
Dec 8 - Dec 9
Total with taxes and fees
The Upper Room
Dining
LAUREL HIGHLANDS GEM ~ FALLINGWATER/OHIOPYLE BOTANICAL HAVEN SUITE with WiFi, AC

LAUREL HIGHLANDS GEM ~ FALLINGWATER/OHIOPYLE BOTANICAL HAVEN SUITE with WiFi, AC

Connellsville
8.0 out of 10, Very Good, (1)
"Such a cool place! Gorgeous interior designs and very comfortable. It felt like being in a museum with walls full of art, crystal chandeliers and antiques. We had the botanical room and it was fun and upbeat. It was a small room but still comfortable. The bed was so soft it was difficult to get in and out of it, but otherwise we really enjoyed it. The exterior is very cool as an historic property. The neighborhood feels a bit neglected but the property itself is great. We stayed here to travel...
United States
Carole
$170 nightly
The price is $188
Dec 8 - Dec 9
Total with taxes and fees
LAUREL HIGHLANDS GEM ~ FALLINGWATER/OHIOPYLE BOTANICAL HAVEN SUITE with WiFi, AC
Exterior
Crow's Nest Crash-Pad

Crow's Nest Crash-Pad

Homestead
8.0 out of 10, Very Good, (2)
"The property was clean, the communication with the manager was fast. It wasn't very sound proof and I could hear the tenants below pretty clearly but was an easy resting place after my conference. "
United States
Khalida S.
$149 nightly
The price is $158
Dec 18 - Dec 19
Total with taxes and fees
Crow's Nest Crash-Pad
Fridge, microwave, oven, stovetop
Charming 3-bedroom townhome with AC and WiFi in Greensburg

Charming 3-bedroom townhome with AC and WiFi in Greensburg

Greensburg
8.8 out of 10, Excellent, (8)
"Great place to stay. Centrally located"
United States
Randall M.
$311 nightly
The price is $343
Dec 8 - Dec 9
Total with taxes and fees
Charming 3-bedroom townhome with AC and WiFi in Greensburg
Fridge, microwave, oven, stovetop
Yough Trail Retreat on the Great Allegheny Passage

Yough Trail Retreat on the Great Allegheny Passage

Connellsville
10.0 out of 10, Exceptional, (14)
"The accommodation was clean and tastefully decorated. The hosts were very welcoming and helpful. Great location to downtown and easy walk to river and trails. Would definitely stay here again! "
United States
Crystal O.
$239 nightly
The price is $264
Dec 31 - Jan 1, 2026
Total with taxes and fees
Yough Trail Retreat on the Great Allegheny Passage
Fridge, microwave, oven, stovetop
Stunning 2 BR King Bed Suite ~ Steps from Walnut

Stunning 2 BR King Bed Suite ~ Steps from Walnut

2.0 star property
Shadyside
10.0 out of 10, Exceptional, (2)
"Host was very helpful and great with responding quickly. Apartment was very roomy and well appointed. Beds very comfortable and great location. I would definitely stay here again."
United States
Mary Beth R.
$129 nightly
The price is $146
Dec 8 - Dec 9
Total with taxes and fees
Stunning 2 BR King Bed Suite ~ Steps from Walnut
Exterior
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.

South Park
10.0 out of 10, Exceptional, (34)
"Fantastic place, exactly what I was looking for, thank you!"
United States
Matthew
$168 nightly
The price is $186
Dec 9 - Dec 10
Total with taxes and fees
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
Terrace/patio
Steps to Bella Terra | Pet Friendly | Fire Pit

Steps to Bella Terra | Pet Friendly | Fire Pit

Hunker
10.0 out of 10, Exceptional, (8)
"The hosts are gracious and available. The home is well-maintained and they have done a great job in providing instructions for the house and the online guide to the area was greatly appreciated. "
United States
Bo N.
$311 nightly
The price is $327
Jan 4 - Jan 5, 2026
Total with taxes and fees
Steps to Bella Terra | Pet Friendly | Fire Pit
Exterior detail
Bright, Comfy Space for 3 | Budget-Friendly Stay

Bright, Comfy Space for 3 | Budget-Friendly Stay

Carrick
9.4 out of 10, Exceptional, (28)
"We didn’t stay very long but we were very comfortable and enjoyed every aspect of the stay. "
United States
Colton M.
$165 nightly
The price is $180
Dec 26 - Dec 27
Total with taxes and fees
Bright, Comfy Space for 3 | Budget-Friendly Stay
Exterior
HostWise Stays - Theater Deck | Podcast Studio | Kid Friendly!

HostWise Stays - Theater Deck | Podcast Studio | Kid Friendly!

2.0 star property
Shadyside
10.0 out of 10, Exceptional, (2)
"The home was decorated in the most charming and esthetic manner. It was very clean, maki g us think we were the first guest. My kids loved the ride on car!"
United States
Lindsay B.
$234 nightly
The price is $265
Dec 8 - Dec 9
Total with taxes and fees
HostWise Stays - Theater Deck | Podcast Studio | Kid Friendly!
Fridge, microwave, oven, stovetop
2615 Jane Down - Southside

2615 Jane Down - Southside

2.0 star property
South Side Flats
10.0 out of 10, Exceptional, (1)
"Location was excellent. The place was very nice, we had a great time."
United States
Leah W.
$170 nightly
The price is $192
Dec 8 - Dec 9
Total with taxes and fees
2615 Jane Down - Southside
Dining tables
Pittsburgh Delight - Cozy 2B/1B Apt w/ Private Parking, Second Floor Unit

Pittsburgh Delight - Cozy 2B/1B Apt w/ Private Parking, Second Floor Unit

East Liberty
10.0 out of 10, Exceptional, (13)
"Spacious unit with modern fixtures; easy walking distance to lots of good restaurants and shops nearby! Quiet neighbors; check out this VRBO for your next stay in Pittsburgh! "
United States
Alexandra H.
$189 nightly
The price is $213
Dec 17 - Dec 18
Total with taxes and fees
Pittsburgh Delight - Cozy 2B/1B Apt w/ Private Parking, Second Floor Unit
Property grounds
Stunning 3BR suite| 2 private decks| A+ Location!

Stunning 3BR suite| 2 private decks| A+ Location!

Shadyside
10.0 out of 10, Exceptional, (1)
"They thought of everything. One of the best properties I’ve stayed at. Everything in the space was done with an eye toward comfort, style and convenience for the traveler. Location close to Downtown and Shadyside/Squirrel Hill/Lawrenceville shoppes and restaurants. Perfect for visits to colleges in Oakland, too. "
United States
William K.
$136 nightly
The price is $153
Dec 8 - Dec 9
Total with taxes and fees
Stunning 3BR suite| 2 private decks| A+ Location!
1 bedroom, desk, iron/ironing board, travel crib
The Walnut Suites - The Onyx Suite

The Walnut Suites - The Onyx Suite

Shadyside
10.0 out of 10, Exceptional, (1)
"Loved our month-long stay!It was a small and very clean place to stay that is walking distance to the best neighborhoods in Pittsburgh!"
United States
Scott C.
$127 nightly
The price is $138
Dec 17 - Dec 18
Total with taxes and fees
The Walnut Suites - The Onyx Suite
Interior
Soothing RV with AC in charming Mount Pleasant/ 2021 Georgetown 5 Series 31L5

Soothing RV with AC in charming Mount Pleasant/ 2021 Georgetown 5 Series 31L5

Mount Pleasant
$229 nightly
The price is $253
Dec 8 - Dec 9
Total with taxes and fees
Soothing RV with AC in charming Mount Pleasant/ 2021 Georgetown 5 Series 31L5
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Madison Hotel Reviews

Holiday Inn Express & Suites Pittsburgh - Monroeville by IHG

Holiday Inn Express & Suites Pittsburgh - Monroeville by IHG

10/10 Excellent
"Everything was great. I will be back in April 2026. Still love the room that has a walk-in shower. Thanks for the great room."
David 2-night trip
Posted 18 hours ago
Holiday Inn Express & Suites Pittsburgh - Monroeville by IHG

Find out more about Madison

Everything you need to know about Madison 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 Madison 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 Madison vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Madison vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Madison. 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 Madison 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 $170 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 Madison rentals

At Expedia, we put the best Madison 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 Madison 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 Madison 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 Madison. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Madison?

Yes, you can find vacation rentals close to well known attractions in Madison, or you can go with a more remote option if you're looking for relaxation.

What are some of the best vacation home rentals that Madison has to offer?

The Light Room: This vacation home rental near Madison has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities like a stovetop and a microwave can make your vacation run smoothly.

What can I see and do in Madison?

Explore the area and family-friendly sights such as Kennywood, or get out into nature at a spot like Madison Park. In the larger area, you’ll find Seton Hill University and The Palace Theatre.

What are vacation rentals like in Madison?

Vacation rentals are privately owned accommodations you can stay in for a couple days or more in Madison. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a vacation rental can provide a sense of safety away from shared hotel elevators and lobbies packed with people while still allowing you to travel. You'll also get more space in a vacation rental than in a hotel, which makes a vacation rental a great choice for family gatherings.