Madison Holiday Rentals

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Check prices for these dates

In two weeks
6 Feb - 8 Feb
In two months
20 Mar - 22 Mar
In three months
17 Apr - 19 Apr
In four months
15 May - 17 May

Our top choices for Madison holiday rentals

Spa

Apartment in Connellsville

Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!
10.0 out of 10, Exceptional, (7 reviews)
"We had a very comfortable cozy stay."
United States
Beth F.
The price is HK$723
HK$1,314 total
includes taxes & fees
26 Jan - 27 Jan
Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!
Property grounds

Chalet in Bear Rocks

Secluded Chalet near Ohiopyle and Seven Springs
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,037
HK$2,033 total
includes taxes & fees
22 Jan - 23 Jan
Secluded Chalet near Ohiopyle and Seven Springs
Private kitchen

Holiday Home in Pittsburgh

Spacious 4-bedroom house in beautiful Pittsburgh
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"The house was beautiful and clean, it fit our group of 10 nicely. The host responded in a timely manner. Overall a great experience here!"
United States
Brooke P.
The price is HK$624
HK$2,536 total
includes taxes & fees
1 Feb - 2 Feb
Spacious 4-bedroom house in beautiful Pittsburgh
Interior

Holiday Home in South Side Flats

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
7.6 out of 10, Good, (9 reviews)
"Home was very comfy children enjoyed there stay I was able to relax and feel comfortable stay I would definitely book again."
United States
bonita f.
The price is HK$312
HK$1,828 total
includes taxes & fees
22 Jan - 23 Jan
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
TV, books

Holiday Home in Mount Pleasant

3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.
2.0 star property
The price is HK$780
HK$1,626 total
includes taxes & fees
1 Feb - 2 Feb
3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.
Interior entrance

Aparthotel in South Side Flats

Kasa South Side Pittsburgh
4.0 star property
8.2 out of 10, Very good, (106 reviews)
"Location to restaurants was great. Elevator was out of order in the parking garage the whole time and had to walk the stairs twice a day. For a week we were there."
United States
Frank
The price is HK$901
HK$1,534 total
includes taxes & fees
7 Feb - 8 Feb
Kasa South Side Pittsburgh
2 bedrooms, desk, iron/ironing board, free WiFi

Apartment in Hunker

Pet-Friendly Stay for Wine Lovers & Event Goers
10.0 out of 10, Exceptional, (8 reviews)
"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.
The price is HK$950
HK$2,510 total
includes taxes & fees
8 Feb - 9 Feb
Pet-Friendly Stay for Wine Lovers & Event Goers
Interior

Holiday Home in Squirrel Hill South

Stylish House near Frick Park
9.8 out of 10, Exceptional, (9 reviews)
"Stayed for the US Open. Check in was easy and property was clean and comfortable. "
United States
Joshua H.
The price is HK$593
HK$1,470 total
includes taxes & fees
26 Jan - 27 Jan
Stylish House near Frick Park
1 bedroom, desk, iron/ironing board, travel cot

Apartment in Friendship

Cozy King Suite|Central, Workspace + Free Parking
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"It was a comfortable place. It had everything we needed, and it was not too far from the Phipps Botanical Gardens and the Carnigie Museum of Art. Near the Airbb was a great coffee shop (literally across the street) and an Aldi for charcuterie items. "
United States
Deborah C.
The price is HK$561
HK$985 total
includes taxes & fees
26 Jan - 27 Jan
Cozy King Suite|Central, Workspace + Free Parking
Property grounds

Apartment in Connellsville

Yough Trail Retreat on the Great Allegheny Passage
10.0 out of 10, Exceptional, (14 reviews)
"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.
The price is HK$1,053
HK$1,894 total
includes taxes & fees
31 Jan - 1 Feb
Yough Trail Retreat on the Great Allegheny Passage
TV

Apartment in East Liberty

Upscale 2BR suite ~ Free Parking & Walkable!
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Very nice clean and affordable and dedicated parking spot a plus. Great location for our Children’s Hospital visit. "
United States
Todd D.
The price is HK$851
HK$1,361 total
includes taxes & fees
22 Jan - 23 Jan
Upscale 2BR suite ~ Free Parking & Walkable!
Interior

Apartment in Shadyside

Stunning 2 BR King Bed Suite ~ Steps from Walnut
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is HK$795
HK$1,297 total
includes taxes & fees
26 Jan - 27 Jan
Stunning 2 BR King Bed Suite ~ Steps from Walnut
Interior

Chalet in Acme

Bright & Clean Chalet
10.0 out of 10, Exceptional, (47 reviews)
"Great place and location"
United States
Rocco R.
The price is HK$2,316
HK$3,882 total
includes taxes & fees
25 Jan - 26 Jan
Bright & Clean Chalet
Private kitchen

Apartment in Wilkinsburg

Comfy Apartment Perfect for a Weekend Stay
2.0 star property
The price is HK$593
HK$1,118 total
includes taxes & fees
25 Jan - 26 Jan
Comfy Apartment Perfect for a Weekend Stay
Interior

Apartment in Shadyside

Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking
9.8 out of 10, Exceptional, (8 reviews)
"Very nice, clean, quiet, and convenient."
United States
Matthew E.
The price is HK$647
HK$924 total
includes taxes & fees
25 Jan - 26 Jan
Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking
Interior

Aparthotel in Connellsville

LAUREL HIGHLANDS GEM~ FALLINGWATER/OHIOPYLE ~ MEDIEVAL CHAMBER SUITE
The price is HK$1,228
HK$2,019 total
includes taxes & fees
27 Jan - 28 Jan
LAUREL HIGHLANDS GEM~ FALLINGWATER/OHIOPYLE ~ MEDIEVAL CHAMBER SUITE
Fridge, microwave, oven, stovetop

Apartment in Shadyside

HostWise Stays - Theater Deck | Podcast Studio | Kid Friendly!
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is HK$694
HK$2,074 total
includes taxes & fees
27 Jan - 28 Jan
HostWise Stays - Theater Deck | Podcast Studio | Kid Friendly!
Interior

Apartment in Shadyside

Shadyside/Pittsburgh, Modern & Accessible 2 Bedroom with Free Parking
10.0 out of 10, Exceptional, (11 reviews)
"Lovely apartment! Very well equipped and located in a great neighborhood with nearby restaurants and cafes. Thanks for a great stay!"
United States
Katy L.
The price is HK$819
HK$1,125 total
includes taxes & fees
22 Jan - 23 Jan
Shadyside/Pittsburgh, Modern & Accessible 2 Bedroom with Free Parking
1 bedroom, iron/ironing board, free WiFi, bed sheets

Apartment in Shadyside

Shadyside/Central @5 Stylish&Bright Studio w/Prkg
10.0 out of 10, Exceptional, (3 reviews)
"Enjoyed this cozy 2nd floor studio apartment. Appreciated the off-street parking. Very quiet in the apartment. Nice neighborhood. Host was very responsive to our questions."
United States
Amy H.
Shadyside/Central @5 Stylish&Bright Studio w/Prkg
Dining

Apartment in South Side Flats

2615 Jane Down - Southside
2.0 star property
10.0 out of 10, Exceptional, (2 reviews)
"Location was excellent. The place was very nice, we had a great time."
United States
Leah W.
The price is HK$542
HK$1,487 total
includes taxes & fees
27 Jan - 28 Jan
2615 Jane Down - Southside
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

The Maverick by Kasa

The Maverick by Kasa

10/10 Excellent
"The king room is unbelievable. So spacious so much more room than the studio. Pay the extra money if you want the space. Hotel is quiet, easy to access and best of all there’s a dining room downstairs"
Cindy 1-night trip
Posted 2 days ago
The Maverick by Kasa

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:

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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?

King bed I 1 block to Carson l Game Room l Fire Pit l BBQ l Sleeps 10 l AC l: This holiday home rental outside of Madison has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.