Madison Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

Our top choices for Madison holiday rentals

Spa

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, (8 reviews)
"We had a very comfortable cozy stay."
United States
Beth F.
The price is HK$461
HK$1,025 total
includes taxes & fees
12 Mar - 13 Mar
Vintage Vogue: Your Stylish Suite with Wi-Fi, Netflix, and Parking!
Property grounds

Secluded Chalet near Ohiopyle and Seven Springs

Secluded Chalet near Ohiopyle and Seven Springs
Bear Rocks
10.0 out of 10, Exceptional, (2 reviews)
"Mike was great. Place is as advertised. Worked well for our weekend at Seven Springs. "
United States
Ryan C.
The price is HK$1,040
HK$2,039 total
includes taxes & fees
11 Mar - 12 Mar
Secluded Chalet near Ohiopyle and Seven Springs
Fridge, microwave, oven, stovetop

Bright & Clean Chalet with Hot Tub

Bright & Clean Chalet with Hot Tub
Acme
10.0 out of 10, Exceptional, (47 reviews)
"Great place and location"
United States
Rocco R.
The price is HK$1,710
HK$3,131 total
includes taxes & fees
11 Mar - 12 Mar
Bright & Clean Chalet with Hot Tub
Property grounds

Yough Trail Retreat on the Great Allegheny Passage

Yough Trail Retreat on the Great Allegheny Passage
Connellsville
10.0 out of 10, Exceptional, (16 reviews)
"Very nice, clean and relaxing would recommend it to anyone and we would for sure come back. A great place to stay if you’re wanting to ride The GAP bike trail"
United States
Patti D.
The price is HK$1,056
HK$1,858 total
includes taxes & fees
11 Mar - 12 Mar
Yough Trail Retreat on the Great Allegheny Passage
TV, books

3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.

3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.
Mount Pleasant
10.0 out of 10, Exceptional, (2 reviews)
"The host was very attentive. The home was well stocked on anything you might need and uniquely decorated. Convenient for our needs. Very nice rural quiet location. The back yard was perfect for our dog to run around. We would stay again. "
United States
Cynthia H.
The price is HK$880
HK$1,707 total
includes taxes & fees
11 Mar - 12 Mar
3-bd home in Mt.Pleasant; child/pet friendly; festivals, biking, skiing nearby.
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Charming 3-bedroom house in soothing West Newton neighborhood

Charming 3-bedroom house in soothing West Newton neighborhood
West Newton
The price is HK$938
HK$1,728 total
includes taxes & fees
12 Mar - 13 Mar
Charming 3-bedroom house in soothing West Newton neighborhood
Property grounds

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
The price is HK$1,564
HK$1,976 total
includes taxes & fees
13 Mar - 14 Mar
Soothing RV with AC in charming Mount Pleasant/ 2021 Georgetown 5 Series 31L5
2 bedrooms, desk, iron/ironing board, free WiFi

Pet-Friendly Stay for Wine Lovers & Event Goers

Pet-Friendly Stay for Wine Lovers & Event Goers
Hunker
10.0 out of 10, Exceptional, (9 reviews)
"Nice property. Responsive owners. Would stay here again."
United States
Ed L.
The price is HK$871
HK$2,417 total
includes taxes & fees
11 Mar - 12 Mar
Pet-Friendly Stay for Wine Lovers & Event Goers
TV

The Light Room

The Light Room
McKeesport
9.6 out of 10, Exceptional, (7 reviews)
"The house has a very peaceful atmosphere."
United States
Susan G.
The price is HK$782
HK$1,460 total
includes taxes & fees
15 Mar - 16 Mar
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, (75 reviews)
"Everything was perfect. Will stay there next trip to see family. "
United States
Joyce P.
The price is HK$915
HK$1,485 total
includes taxes & fees
12 Mar - 13 Mar
Cozy Studio with Unique Charm in Private Setting
1 bedroom, desk, WiFi, bed sheets

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

3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
Squirrel Hill
10.0 out of 10, Exceptional, (3 reviews)
"It was a pleasure staying there"
United States
msimchowitz
The price is HK$306
HK$1,586 total
includes taxes & fees
11 Mar - 12 Mar
3min>Carnegie Mellon University:UPMC Shadyside:3min>CMU:Full Kitchen
Terrace/patio

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!

Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
Plum
10.0 out of 10, Exceptional, (17 reviews)
"It was a very nice property, very clean, great neighborhood and area."
United States
A. Ben K.
The price is HK$1,329
HK$2,301 total
includes taxes & fees
15 Mar - 16 Mar
Pet-friendly home next to Oakmont & Veltre's + a few miles to Pittsburgh events!
Smart TV

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 reviews)
"Great place to stay. Centrally located"
United States
Randall M.
The price is HK$1,564
HK$2,702 total
includes taxes & fees
13 Mar - 14 Mar
Charming 3-bedroom townhome with AC and WiFi in Greensburg
Dining

Hydee's Hideaway

Hydee's Hideaway
Swissvale
10.0 out of 10, Exceptional, (25 reviews)
"The location was great and the property owners were kind and helped us during our stay. "
United States
Cathy K.
The price is HK$1,056
HK$2,850 total
includes taxes & fees
11 Mar - 12 Mar
Hydee's Hideaway
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, (37 reviews)
"The lily pad was very clean and comfortable! There’s a nice porch with a pond, thanks for being a great host!"
United States
Jamie G.
The price is HK$1,017
HK$1,623 total
includes taxes & fees
22 Mar - 23 Mar
LILY PAD: Cozy Cabin with Unique Charm overlooking small pond on our property.
Interior

Stylish House near Frick Park

Stylish House near Frick Park
Squirrel Hill South
9.8 out of 10, Exceptional, (9 reviews)
"Cozy house, had everything we needed in a very convenient location."
United States
Warren S.
The price is HK$704
HK$1,600 total
includes taxes & fees
31 Mar - 1 Apr
Stylish House near Frick Park
Exterior detail

Shadyside/Central @2 Bright and Stylish Studio with Free Parking

Shadyside/Central @2 Bright and Stylish Studio with Free Parking
Shadyside
10.0 out of 10, Exceptional, (4 reviews)
"Great place to stay! Location was perfect for us, and offstreet parking was a plus. We were within walking distance of several shops and restaurants. We will definitely stay here again!"
United States
Denise J.
Shadyside/Central @2 Bright and Stylish Studio with Free Parking
Interior

Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!

Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
Monongahela
10.0 out of 10, Exceptional, (12 reviews)
"The house was very spacious and cozy and Andres was very responsive to anything we needed. We loved our stay!"
United States
Marissa M.
The price is HK$1,000
HK$2,175 total
includes taxes & fees
16 Mar - 17 Mar
Charming 4-bedroom family friendly house in Monongahela. Make yourself at home!
Interior

Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking

Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking
Shadyside
9.8 out of 10, Exceptional, (8 reviews)
"Very nice, clean, quiet, and convenient."
United States
Matthew E.
The price is HK$649
HK$927 total
includes taxes & fees
11 Mar - 12 Mar
Shadyside/Pittsburgh, Modern & Stylish 1 Bedroom with Free Parking
Interior

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

Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
South Side Flats
7.6 out of 10, Good, (10 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$297
HK$1,832 total
includes taxes & fees
11 Mar - 12 Mar
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of 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

Hyatt House Pittsburgh/Bloomfield/Shadyside

Hyatt House Pittsburgh/Bloomfield/Shadyside

10/10 Excellent
"Parking was "
Jake 1-night trip
Posted 4 hours ago
Hyatt House Pittsburgh/Bloomfield/Shadyside

Find out more about Madison

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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?

Enjoy Urban Living at our Steel City Getaway w/ Seasonal Hot Tub!: This holiday home rental outside of Madison is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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.