Madison Holiday Rentals

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
5 Dec - 6 Dec
Tomorrow
6 Dec - 7 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Madison

Exterior
Kasa South Side Pittsburgh

Kasa South Side Pittsburgh

4.0 star property
South Side Flats
8.2 out of 10, Very good, (105)
"Clean great views hotel "
United States
Shomario
The price is HK$1,112
HK$1,774 total
includes taxes & fees
7 Dec - 8 Dec
Kasa South Side Pittsburgh
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.
The price is HK$700
HK$1,320 total
includes taxes & fees
7 Dec - 8 Dec
The Light Room
Microwave, oven, stovetop
California king wet room suite

California king wet room suite

West Homestead
9.4 out of 10, Exceptional, (3)
"Water could have been hotter in the wet room but other than that was as advertised."
United States
brandon b.
The price is HK$1,167
HK$1,514 total
includes taxes & fees
15 Dec - 16 Dec
California king wet room suite
Smart TV
Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm

Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm

Greensburg
10.0 out of 10, Exceptional, (13)
"Great time host was awesome "
United States
Andrew M.
Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm
4 bedrooms, desk, WiFi, bed sheets
Urban Oasis in Point Breeze 4BR Industrial-Style Apartment

Urban Oasis in Point Breeze 4BR Industrial-Style Apartment

Point Breeze North
9.0 out of 10, Wonderful, (2)
"Very large nice space! "
United States
Sadie T.
Urban Oasis in Point Breeze 4BR Industrial-Style Apartment
Smart TV, fireplace
Home away from home!!!

Home away from home!!!

Monroeville
8.0 out of 10, Very good, (37)
"Kitchen/living room great area for us to congregate and visit"
United States
jean d.
The price is HK$2,977
HK$5,058 total
includes taxes & fees
10 Dec - 11 Dec
Home away from home!!!
Fridge, microwave, oven, stovetop
Clean and comfortable 3BR home in the South Side neighborhood

Clean and comfortable 3BR home in the South Side neighborhood

South Side Slopes
10.0 out of 10, Exceptional, (39)
"Exceeded expectations. Beautifully maintained property conveniently located for our visit to Pittsburgh. Quiet neighborhood but close to everything.We look forward to returning!"
United States
B.R. P.
Clean and comfortable 3BR home in the South Side neighborhood
Living area
Charming 2-bedroom building with fitness room and AC in Clairton

Charming 2-bedroom building with fitness room and AC in Clairton

Clairton
2.0 out of 10, (1)
The price is HK$911
HK$1,479 total
includes taxes & fees
7 Dec - 8 Dec
Charming 2-bedroom building with fitness room and AC in Clairton
Terrace/patio
Cozy unique space in serene West Homestead with sauna and outdoor hot tub.

Cozy unique space in serene West Homestead with sauna and outdoor hot tub.

West Homestead
10.0 out of 10, Exceptional, (1)
"Everything was perfect and as expected "
United States
Jonathan M.
The price is HK$1,051
HK$1,364 total
includes taxes & fees
7 Dec - 8 Dec
Cozy unique space in serene West Homestead with sauna and outdoor hot tub.
Exterior detail
Shadyside Penthouse

Shadyside Penthouse

Shadyside
6.4 out of 10, (15)
"This place has lots of room- four large bedrooms in addition to a living room and kitchen. Great communication with the host and convenient to Pitt, CMU, and shopping. A great rental for a large group!"
United States
Megan T.
Shadyside Penthouse
Outdoor dining
Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!

Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!

Squirrel Hill South
9.8 out of 10, Exceptional, (46)
"Great property as advertised. Very clean and comfortable."
Canada
George B.
Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!
Interior
4 br 2 baClassical Victorian Home Off Walnut Street in Shadyside Pittsburgh

4 br 2 baClassical Victorian Home Off Walnut Street in Shadyside Pittsburgh

Shadyside
10.0 out of 10, Exceptional, (5)
"Great property, great location. Seamless experience, no fuss. Great for our adult group get-together. Can't wait to stay there again. "
United States
Paul and Audria R.
4 br 2 baClassical Victorian Home Off Walnut Street in Shadyside Pittsburgh
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.
The price is HK$840
HK$1,400 total
includes taxes & fees
7 Dec - 8 Dec
Cozy Studio with Unique Charm in Private Setting
Interior
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

Pittsburgh Home Near Frick Park, 7 Mi to Dtwn

3.0 star property
Wilkinsburg
Pittsburgh Home Near Frick Park, 7 Mi to Dtwn
Smart TV
Allegheny Riverside One Bedroom Suite

Allegheny Riverside One Bedroom Suite

2.0 star property
Pittsburgh
9.2 out of 10, Wonderful, (7)
"Train tracks are right behind the property and run in the evenings. Because there is a crossing close by the train blows its whistle. Our stay had a couple trains after midnight with whistles that woke us up each night"
United States
Christine
Allegheny Riverside One Bedroom Suite
Living area
Lovely 3-bedroom house in the heart of downtown Pittsburgh.

Lovely 3-bedroom house in the heart of downtown Pittsburgh.

2.0 star property
Oakland
Lovely 3-bedroom house in the heart of downtown Pittsburgh.
Smart TV, video games
Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location!

Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location!

South Side Slopes
9.8 out of 10, Exceptional, (51)
"Perfect for what we wanted. Loved the hot tub and the outdoor lounge area. There were 7 of us and plenty of beds for everyone! Thoroughly enjoyed our stay."
United States
Betty Jane W.
Pittsburgh’s Tropicana with outdoor year round hot tub. Fantastic location!
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.
The price is HK$739
HK$1,364 total
includes taxes & fees
7 Dec - 8 Dec
The Upper Room
Private kitchen
Spacious 3BR Home near Downtown, Oakland & East Liberty! Max 15 nights by RedAwning

Spacious 3BR Home near Downtown, Oakland & East Liberty! Max 15 nights by RedAwning

3.5 star property
Wilkinsburg
Spacious 3BR Home near Downtown, Oakland & East Liberty! Max 15 nights by RedAwning
Smart TV
3-bedroom townhome in delightful Pittsburgh with WiFi, AC

3-bedroom townhome in delightful Pittsburgh with WiFi, AC

East Liberty
8.0 out of 10, Very good, (1)
"Great location for short drives to the sites in Pittsburgh. Can walk to restaurants and stores. "
United States
Wendy L.
The price is HK$1,362
HK$2,335 total
includes taxes & fees
2 Jan - 3 Jan 2026
3-bedroom townhome in delightful Pittsburgh with WiFi, AC
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

Hotel Indigo Pittsburgh University-Oakland by IHG

Hotel Indigo Pittsburgh University-Oakland by IHG

10/10 Excellent
"Staff, Clean room. TV and lobby computersuch disappointment."
Barry 2-night trip
Posted 1 day ago
Hotel Indigo Pittsburgh University-Oakland by IHG

Find out more about Madison

Search for holiday rentals in Madison on Expedia! You can easily find your home rentals, villas, holiday apartments in Madison using one of the methods below:

  • View our selection of featured holiday rentals in Madison
  • Use the map to find apartments and other holiday homes in the Madison neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Madison while they last

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

Frequently asked questions

Are there holiday rentals in Madison?

Yes, there are holiday rentals close to the most popular sights in Madison, or you can select a more secluded option if you're looking for a relaxing stay.

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

The Light Room: This holiday home rental outside of Madison has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities such as a stovetop and a microwave can make your holiday 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 wider area, you’ll find Seton Hill University and The Palace Theatre.

What are holiday rentals like in Madison?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Madison. Holiday rentals provide amenities such as laundry facilities and kitchens so you'll have a home away from home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for family trips.