Madison Holiday Rentals

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Check prices for these dates

In two weeks
19 Sept - 21 Sept
In one month
3 Oct - 5 Oct
In two months
31 Oct - 2 Nov
In three months
28 Nov - 30 Nov

Holiday Rentals in Madison

Our top choices for Madison holiday rentals

Kasa South Side Pittsburgh
Exterior

Kasa South Side Pittsburgh

4.0 star property
8.2 out of 10, Very good, (91)
"Clean great views hotel "
Kasa South Side Pittsburgh
Home away from home!!!
Smart TV, fireplace

Home away from home!!!

8.8 out of 10, Excellent, (31)
"Great, clean, perfect location"
The price is HK$2,984
HK$5,070 total
includes taxes & fees
6 Sept - 7 Sept
Home away from home!!!
Shadyside Penthouse
Exterior detail

Shadyside Penthouse

6.8 out of 10, (13)
"We were in Pittburgh for our child's graduation. While the overall physical space is as described and the location was very good, the house was undergoing some renovation and was very sparse in terms of furniture. Moreover, there were many flies in the house, missing pillow case covers, and some spaces required additional cleaning. "
Shadyside Penthouse
Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!
Outdoor dining

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

9.8 out of 10, Exceptional, (43)
"The house and location was perfect for our girlfriend get away. Location was convenient to museums and attractions. Owner was easy to work with. Would definitely stay here again. "
Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Fridge, microwave, oven, stovetop

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.4 out of 10, Very good, (28)
"got a lil warm in the house the first night but over all a great place"
The price is HK$312
HK$1,846 total
includes taxes & fees
7 Sept - 8 Sept
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm
Smart TV

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

10.0 out of 10, Exceptional, (6)
"We thoroughly enjoyed our stay at the farmhouse and Gina was a terrific host. She was very communicative throughout our entire stay, met us upon arrival (it was late in the evening too) for a quick tour, and provided us with some helpful local recommendations for meals. We'd definitely book here again if we're back in the area."
Peaceful 3-Bedroom Country Farmhouse Situated on 125 Acre Horse Farm
Charming 3-bedroom house in Delmont with WiFi and AC
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Delmont with WiFi and AC

9.6 out of 10, Exceptional, (4)
"We were there for USOpen. Nice, easy place with great communication with host "
The price is HK$975
HK$2,130 total
includes taxes & fees
4 Oct - 5 Oct
Charming 3-bedroom house in Delmont with WiFi and AC
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
Exterior

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

10.0 out of 10, Exceptional, (31)
"Fantastic place, exactly what I was looking for, thank you!"
The price is HK$936
HK$1,524 total
includes taxes & fees
10 Sept - 11 Sept
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
Easy access, roomy, close to so much but in a private country setting.
Terrace/patio

Easy access, roomy, close to so much but in a private country setting.

10.0 out of 10, Exceptional, (59)
"From the moment we pulled in the driveway, Chet made us feel right at home. The house is very clean. The hosts pay close attention to detail to make their guests comfortable. Great communication throughout our stay. Convenient location near the turnpike, but it is in a secluded area allowing peace and quiet. Will certainly stay again!"
Easy access, roomy, close to so much but in a private country setting.
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Fridge, microwave, oven, stovetop

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!

7.0 out of 10, Good, (6)
"Tom was very communicative during the whole stay and had great recommendations! We loved the place, well situated on the South side for easy walking along Carson. Wonderful time in Pittsburgh! "
The price is HK$351
HK$1,890 total
includes taxes & fees
7 Sept - 8 Sept
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
💜Highland Park Hideaway - Private Deck Space and Free Parking💜
Fridge, microwave, oven, stovetop

💜Highland Park Hideaway - Private Deck Space and Free Parking💜

8.2 out of 10, Very good, (25)
"Host showed great communication and the property was very clean and comfortable."
The price is HK$406
HK$1,827 total
includes taxes & fees
17 Sept - 18 Sept
💜Highland Park Hideaway - Private Deck Space and Free Parking💜
King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l
Private kitchen

King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l

The price is HK$1,061
HK$3,644 total
includes taxes & fees
7 Sept - 8 Sept
King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l
Chic 1-bedroom apartment with WiFi, AC in brilliant Pittsburgh
Outdoor dining

Chic 1-bedroom apartment with WiFi, AC in brilliant Pittsburgh

9.6 out of 10, Exceptional, (12)
"Cutest room, loved the TV room with all the windows. Owner was super nice and the area was great. As a female staying alone, I highly recommend this place! I felt safe and comfortable! "
Chic 1-bedroom apartment with WiFi, AC in brilliant Pittsburgh
Kasa See a Show at Kelly Strayhorn Theater The Maverick
Room

Kasa See a Show at Kelly Strayhorn Theater The Maverick

2.0 star property
The price is HK$819
HK$1,075 total
includes taxes & fees
29 Sept - 30 Sept
Kasa See a Show at Kelly Strayhorn Theater The Maverick
Bright, Comfy Space for 3 | Budget-Friendly Stay
Exterior detail

Bright, Comfy Space for 3 | Budget-Friendly Stay

9.6 out of 10, Exceptional, (26)
"We had a great stay! Was the perfect cute and cozy place for our little trip."
Bright, Comfy Space for 3 | Budget-Friendly Stay
✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds
Interior

✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds

2.0 star property
10.0 out of 10, Exceptional, (4)
"Older style home, but well maintained. Quiet neighborhood, comfortable beds, enjoy the welcome sign. Host was very attentive prior and during our stay. "
✰Self Check-In✰Backyard✰Decks✰Full Kitchen✰W/D✰Smart TVs✰FREE Parking✰Cozy Beds
Hidden Gem in Swissvale sleeps 6
Interior

Hidden Gem in Swissvale sleeps 6

9.4 out of 10, Exceptional, (31)
"Wonderful place. Just where we needed to be. Host was very responsive with all questions!!! I will defiantly stay here again!!!"
Hidden Gem in Swissvale sleeps 6
Minimalist Townhouse with Stunning Skyline View
Property grounds

Minimalist Townhouse with Stunning Skyline View

10.0 out of 10, Exceptional, (12)
"Good for a short stay "
The price is HK$2,769
HK$4,530 total
includes taxes & fees
26 Sept - 27 Sept
Minimalist Townhouse with Stunning Skyline View
City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington
Living area

City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington

2.0 star property
9.8 out of 10, Exceptional, (7)
"We had the best time in Pittsburgh! Absolutely amazing host! Would highly recommend this house to anyone! Cant wait to stay again next year! "
The price is HK$2,925
HK$5,039 total
includes taxes & fees
7 Sept - 8 Sept
City Living—sleeps 12 15-20 mins from Acrisure Stadium, PNC Park, Mt Washington
3-bedroom townhome in delightful Pittsburgh with WiFi, AC
Smart TV

3-bedroom townhome in delightful Pittsburgh with WiFi, AC

8.0 out of 10, Very good, (1)
"Great location for short drives to the sites in Pittsburgh. Can walk to restaurants and stores. "
The price is HK$1,365
HK$2,490 total
includes taxes & fees
7 Sept - 8 Sept
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.
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Top Madison Hotel Reviews

Find out more about Madison

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?

Home away from home!!!: This holiday home rental outside of Madison offers a fireplace, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What can I see and do in Madison?

Explore the area and family-friendly sights such as Stone Villa Wine Cellars, 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.