Holiday Homes in South Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in South Side

Stylish & Central 3BD Home Pittsburgh/North Side
TV

Stylish & Central 3BD Home Pittsburgh/North Side

10.0 out of 10, Exceptional, (9)
"Super clean and comfortable. Centrally located. Great for family. Everyone enjoyed their stay."
The price is NZ$211
includes taxes & fees
11 Aug - 12 Aug
Stylish & Central 3BD Home Pittsburgh/North Side
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
Over The Bar Bicycle Cafe offers a variety of services and products, including a selection of beers.

Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside

6.0 out of 10, (3)
"Excellent communication with owner. Fast, friendly and courteous. Located about 450 meter walk up a large hill from Penn Avenue (bus 88) which is about 35 minutes to downtown. Apartment showing its age but fair value for cost. "
The price is NZ$551
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom house with AC, WiFi in lovely Pittsburgh Southside
Stylish 4Bdr Loft Home, North Shore, City Skyline
TV, fireplace

Stylish 4Bdr Loft Home, North Shore, City Skyline

10.0 out of 10, Exceptional, (28)
"Would definitely stay again. No problems whatsoever Recommend"
The price is NZ$293
includes taxes & fees
17 Aug - 18 Aug
Stylish 4Bdr Loft Home, North Shore, City Skyline
Historic 4 Bed Northside Home - Amazing Location
Enjoy meals in this traditional dining area with a glass-top table and four chairs, surrounded by a forest-themed mural.

Historic 4 Bed Northside Home - Amazing Location

7.4 out of 10, Good, (13)
"The property was exactly as expected, the pictures are very accurate. Property owner was very kind and responsive. Would definitely stay here again."
Historic 4 Bed Northside Home - Amazing Location
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view
Enjoy cooking and dining in this well-equipped kitchen with a central island and ample counter space.

Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view

2.0 star property
9.8 out of 10, Exceptional, (16)
"Great house and great location. Walking distance to several bars, restaurants and the incline. Great views. "
Spacious 3-bedroom house in scenic Mt. Washington near Grandview's city view
Quick ride to the Stadiums!
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and gas stove, plus a convenient patio area with outdoor seating.

Quick ride to the Stadiums!

10.0 out of 10, Exceptional, (11)
"The house is beautiful and was perfect for an overnight with family after strolling around north shore all day. The house was stocked with everything we needed, the beds were so comfortable, and I will go back! Thanks for a great stay!"
The price is NZ$501
includes taxes & fees
11 Aug - 12 Aug
Quick ride to the Stadiums!
The Beverly at Mt. Lebanon by Luxe PGH
Enjoy cooking in this well-equipped kitchen with a central island, microwave, and oven, surrounded by white cabinetry and a black countertop.

The Beverly at Mt. Lebanon by Luxe PGH

4.0 star property
6.0 out of 10, (13)
"Beautiful place"
The Beverly at Mt. Lebanon by Luxe PGH
2 King Beds | Free Parking | BBQ | Arcade | Patio
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and dishwasher.

2 King Beds | Free Parking | BBQ | Arcade | Patio

9.8 out of 10, Exceptional, (26)
"Had a great stay with 3 friends and our 7 year old boys for Pirates games. Would definitely stay here again!"
The price is NZ$572
includes taxes & fees
8 Sept - 9 Sept
2 King Beds | Free Parking | BBQ | Arcade | Patio
6 Mi to Dtwn: Pittsburgh Townhome w/ Porch
Enjoy cooking in this well-lit kitchen with a stainless steel range hood, dishwasher, stove, and microwave.

6 Mi to Dtwn: Pittsburgh Townhome w/ Porch

9.8 out of 10, Exceptional, (37)
"The stay was wonderful."
6 Mi to Dtwn: Pittsburgh Townhome w/ Porch
The Victoria
Relax in this inviting outdoor seating area with a comfortable sofa set and a coffee table.

The Victoria

2.0 star property
10.0 out of 10, Exceptional, (17)
"Was a wonderful weekend stay in Pittsburgh. Great house and lots of space. Beautiful backyard area "
The Victoria
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
Enjoy cooking in this well-equipped kitchen with a central island and dishwasher.

Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh

10.0 out of 10, Exceptional, (14)
"Perfect location and charming feel"
Charming Hydrangea Cottage in Sewickley Village 4bd/1.5 b - 20 min to Pittsburgh
King Bed | Free Parking | BBQ | Fire pit | Arcade
Enjoy cooking in this well-lit kitchen with a central island and bar seating.

King Bed | Free Parking | BBQ | Fire pit | Arcade

9.6 out of 10, Exceptional, (57)
"We stayed over the Christmas holiday and really enjoyed the townhouse - lots of privacy and room for the whole family. Also loved the convenient location. "
The price is NZ$586
includes taxes & fees
20 Aug - 21 Aug
King Bed | Free Parking | BBQ | Fire pit | Arcade
Momma Mary's Place @ Lawrenceville
Kitchen equipped with a stainless steel range hood, microwave, and kettle, as well as a dishwasher and tiled backsplash.

Momma Mary's Place @ Lawrenceville

9.6 out of 10, Exceptional, (27)
"We came up for a Pittsburgh game stayed 2 nights lots to see. Great little place to stay had a great time"
Momma Mary's Place @ Lawrenceville
3 Bed - Million Dollar View -Off Street Parking!
Enjoy dining or socializing in this tranquil outdoor space overlooking the water.

3 Bed - Million Dollar View -Off Street Parking!

9.2 out of 10, Wonderful, (29)
"Views were awesome place was great. I would definitely stay there again."
The price is NZ$685
includes taxes & fees
12 Aug - 13 Aug
3 Bed - Million Dollar View -Off Street Parking!
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Kitchen features a stainless steel range hood, oven, and large refrigerator, along with white cabinetry and a wooden floor.

Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village

9.8 out of 10, Exceptional, (7)
"We truly enjoyed our stay at this comfortable home in Sewickley Village! Everything worked out perfectly and walking around town so easily due to the convenient location was ideal!"
Home away from home! Amenity-filled 3BR, 1.5BA home in Sewickley Village
Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking
Enjoy outdoor dining or relaxation on the covered patio with two chairs and a table.

Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking

9.2 out of 10, Wonderful, (16)
"We stayed for two weeks it was perfect"
Cozy home close to UPMC/CMU/UPITT/DUQSNE/CARLW Minutes from everything w/Parking
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, along with a sink and ample counter space.

❤️Cozy Townhome on Carey with Private Deck Space ❤️

8.6 out of 10, Excellent, (26)
"got a lil warm in the house the first night but over all a great place"
The price is NZ$410
includes taxes & fees
11 Aug - 12 Aug
❤️Cozy Townhome on Carey with Private Deck Space ❤️
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
Enjoy a convenient morning with a coffee maker and toaster, plus a stove, microwave, and refrigerator.

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

9.4 out of 10, Exceptional, (3)
"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 NZ$410
includes taxes & fees
11 Aug - 12 Aug
Carey Cottage 🏡 - Cozy 3BR Stay in ❤️ of Southside!
View from the Top! Steps from Grandview, Sleeps 8
Relax in this stylish living room with a large sofa, coffee table, and cityscape art.

View from the Top! Steps from Grandview, Sleeps 8

10.0 out of 10, Exceptional, (52)
"Place was great, hosts were very pleasant and helpful, really nice neighborhood very conveniently located to downtown and other parts of the city. Highly recommended."
View from the Top! Steps from Grandview, Sleeps 8
Home away from home!!!
Relax in this open-plan living space featuring a sofa, dining area, and fully equipped kitchen.

Home away from home!!!

8.8 out of 10, Excellent, (30)
"Great, clean, perfect location"
The price is NZ$841
includes taxes & fees
11 Aug - 12 Aug
Home away from home!!!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top South Side Hotel Reviews

Drury Plaza Hotel Pittsburgh Downtown

Drury Plaza Hotel Pittsburgh Downtown

10/10 Excellent
"The hotel was clean, bright and very friendly. The amenities were great with two meals offered- breakfast and a light dinner-and valet car parking. Everyone on staff was courteous and extremely friendly, and they went out of their way to assist us. The room was clean and the beds were comfortable. The bathroom was also very clean and the shower stayed hot and gave good water pressure."
Michelle 2-night trip
Posted 12 hours ago
Drury Plaza Hotel Pittsburgh Downtown