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Holiday Homes in Pittsburgh

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Pittsburgh holiday homes

A grassy outdoor area with a wooden bench, a stone statue, and a wooden fence.

1. Explore Pittsburgh from a Modern, Hip Bungalow

Explore Pittsburgh from a Modern, Hip Bungalow
North Side
9.6 out of 10, Exceptional, (71 reviews)
"The property is extremely pet friendly! The house was clean and had everything you could want to have a relaxing experience. Very close to downtown. Lovely backyard. You won't regret staying there."
United States
Gabriellia
The price is €164
includes taxes & fees
21 Aug - 22 Aug
Explore Pittsburgh from a Modern, Hip Bungalow
A living room with a green sofa, a coffee table, and a chair. There is a coat rack and a television on the wall.

2. 1210 James St. #1 ★Pro Cleaned

1210 James St. #1 ★Pro Cleaned
North Side
9.8 out of 10, Exceptional, (12 reviews)
"House was very clean and comfortable. Was conveniently located and we were able to quickly get to everywhere we needed to go. "
United States
Donna Huntermark L.
1210 James St. #1 ★Pro Cleaned
A modern kitchen with white cabinetry, a central island, and a dining area with a clear table.

3. Free Parking★Walk Everywhere!★2 Private bathrooms!

Free Parking★Walk Everywhere!★2 Private bathrooms!
North Side
9.8 out of 10, Exceptional, (42 reviews)
"Had everything we needed for a lovely stay. Close to stuff to do and eat. Very clean and overall a great experience."
United States
mark d.
Free Parking★Walk Everywhere!★2 Private bathrooms!
A kitchen with white cabinets, a marble countertop, and a chalkboard wall with various writings and drawings.

4. M&J - 823 James St.

M&J - 823 James St.
North Side
10.0 out of 10, Exceptional, (11 reviews)
"A few coworkers and I stayed here to attend a work conference; it was the perfect home away from home. "
United States
Ashley M.
The price is €215
includes taxes & fees
24 Aug - 25 Aug
M&J - 823 James St.
A cityscape with a river, a bridge, and a pedestrian walkway.

5. Urban Retreat with Garage on Mt. Washington

Urban Retreat with Garage on Mt. Washington
Mount Washington
9.8 out of 10, Exceptional, (95 reviews)
"Great place! Short walk to cool areas "
United States
David M.
The price is €194
includes taxes & fees
25 Aug - 26 Aug
Urban Retreat with Garage on Mt. Washington
A modern living room with a sectional sofa, a coffee table with a plant, a floor lamp, and a geometric rug. There are two chairs and a small table in the background.

6. M&J - Emlin 513 St.

M&J - Emlin 513 St.
North Side
9.8 out of 10, Exceptional, (22 reviews)
"Great location / neighborhood and the host was very easy to work with and responsive "
United States
Gerrit v.
M&J - Emlin 513 St.
A living room with a fireplace, a television, and a dining area with a table and chairs.

7. HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere

HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
South Side Flats
9.6 out of 10, Exceptional, (4 reviews)
"The property was outstanding, nicely appointed and quite comfortable. Close to downtown without being IN downtown, thus very well-located for everywhere we needed to be. Service was excellent, our questions were answered promptly and with the right amount of detail. "
United States
Butch K.
The price is €195
includes taxes & fees
25 Aug - 26 Aug
HostWise Stays - Southside Gem – Patio, Smart TVs, Walk Everywhere
A modern kitchen with white cabinetry, granite countertops, stainless steel appliances, and a unique spiral pendant light.

8. Stylish & Central 3BD Home Pittsburgh/North Side with Free Street Parking

Stylish & Central 3BD Home Pittsburgh/North Side with Free Street Parking
North Side
9.2 out of 10, Wonderful, (35 reviews)
"We had a great stay. Only needed for overnight. The house was clean and neat and pretty close to any activities."
United States
Derrick C.
The price is €137
includes taxes & fees
24 Aug - 25 Aug
Stylish & Central 3BD Home Pittsburgh/North Side with Free Street Parking
A living room with a fireplace, a sofa, a coffee table, and two paintings on the wall.

9. Eclectic Historic Sunny Vista Home with City Views, Northshore

Eclectic Historic Sunny Vista Home with City Views, Northshore
North Side
9.6 out of 10, Exceptional, (41 reviews)
"Awesome place to stay. Clean and comfortable. Lisa was great. Easy access to public transportation downtown. We will be back again. Highly recommend this place."
United States
William G.
Eclectic Historic Sunny Vista Home with City Views, Northshore
A cozy living room with a brick fireplace, a wooden dining table, and a staircase.

10. 1209 Ocala St Pittsburgh

1209 Ocala St Pittsburgh
North Side
10.0 out of 10, Exceptional, (42 reviews)
"The house was very cool place - lots of interesting touches, very clean and had everything we needed.The host was so easy to communicate with and provided very clear instructions, which was very important regarding the parking.The location was also perfect - easy walking distance to PNC Park, the River Trail and other landmarks.We would definitely stay here again and are already looking forward to our next visit!!"
United States
Mary B.
1209 Ocala St Pittsburgh
A modern kitchen with a white brick wall, a flat-screen TV mounted above a wooden shelf, and a bar area with stools.

11. 307 37th St · Lawrenceville Row House - Walk to Everything!

307 37th St · Lawrenceville Row House - Walk to Everything!
Lawrenceville
9.4 out of 10, Exceptional, (47 reviews)
"Great location and very comfortable beds!"
United States
Cassi D.
The price is €169
includes taxes & fees
24 Aug - 25 Aug
307 37th St · Lawrenceville Row House - Walk to Everything!
A modern living room with a fireplace, a staircase, and a view of the outdoors.

12. 1207 Ocala - Boat House - North Side

1207 Ocala - Boat House - North Side
North Side
10.0 out of 10, Exceptional, (38 reviews)
"Very attentive hosts! The house is charming and welcoming. We loved our stay and will be coming back"
United States
anna a.
The price is €391
includes taxes & fees
18 Sept - 19 Sept
1207 Ocala - Boat House - North Side
A modern living room with a sofa, two armchairs, a coffee table, and a fireplace.

13. Stylish 4Bdr Loft Home, North Shore, City Skyline with Free Street Parking

Stylish 4Bdr Loft Home, North Shore, City Skyline with Free Street Parking
North Side
9.4 out of 10, Exceptional, (78 reviews)
"Fantastic stay, well designed and clean."
United States
Joe G.
The price is €137
includes taxes & fees
20 Sept - 21 Sept
Stylish 4Bdr Loft Home, North Shore, City Skyline with Free Street Parking
A modern kitchen with wooden accents, a dining area with a table and chairs, and a gray sofa with patterned cushions.

14. Lovely Strip District loft with free parking

Lovely Strip District loft with free parking
Strip District
10.0 out of 10, Exceptional, (38 reviews)
"Great location and really nice property."
United States
Tracy H.
The price is €162
includes taxes & fees
23 Aug - 24 Aug
Lovely Strip District loft with free parking
A residential building with a white door, brick walls, and a small outdoor area with steps leading to the door.

15. Walkable Luxury 4 Br House

Walkable Luxury 4 Br House
North Side
9.2 out of 10, Wonderful, (27 reviews)
"We loved this property, it was so charming and host was great."
United States
Misty F.
The price is €273
includes taxes & fees
24 Aug - 25 Aug
Walkable Luxury 4 Br House
A living room with a grey sofa, yellow and white cushions, a wooden coffee table, and a modern floor lamp.

16. Recently refurbished, great location, walking distance to bars & restaurants!

Recently refurbished, great location, walking distance to bars & restaurants!
Bloomfield
10.0 out of 10, Exceptional, (4 reviews)
"Close in poximity to relatives. Walkable neighborhood, with lots of resturants and shops near by. Nice house with just about evertything you would need for the perfect get away."
United States
Susie Rinehart
Recently refurbished, great location, walking distance to bars & restaurants!
A modern living room with a sofa, ottomans, a coffee table, and a ceiling fan.

17. ★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!

★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
North Side
10.0 out of 10, Exceptional, (54 reviews)
"Amenities were great, place was very clean and the location was excellent "
United States
Cynthia T.
★ HostWise Stays ★ Pet Friendly, Balcony & Patio, and an easy walk to bars & restaurants!
A neatly made bed with a white comforter and a yellow throw blanket, a wooden headboard with intricate carvings, and a bookshelf filled with books.

18. Beautiful Strip District Studio w/ Outdoor Loggia

Beautiful Strip District Studio w/ Outdoor Loggia
Strip District
9.6 out of 10, Exceptional, (48 reviews)
"Everything was neat and clean, with exceptional attention to detail. The furnishings were charming, complementing the property and the neighborhood. Free designated parking was a big plus! The host did an outstanding job foreseeing our comfort and needs."
United States
Randy T.
Beautiful Strip District Studio w/ Outdoor Loggia
A compact kitchen with a white door, grey cabinets, a sink, and a wooden countertop.

19. Cozy escape close to downtown, stadiums & parks

Cozy escape close to downtown, stadiums & parks
North Side
9.8 out of 10, Exceptional, (70 reviews)
"Cute and cozy little house! Very clean and bed was comfortable, Lisa is an excellent host! We enjoyed our stay! "
United States
Jennifer B.
Cozy escape close to downtown, stadiums & parks

20. ★ HostWise Stays ★ Tech Stay w/ In-Home Cinema & Secure Parking Spot

★ HostWise Stays ★ Tech Stay w/ In-Home Cinema & Secure Parking Spot
North Side
9.8 out of 10, Exceptional, (8 reviews)
"Host was great - very fast responses and pleasant. The house is really nice, fully equipped and comfortable for everyone especially with 3.5 bathrooms . Highly recommend!"
United States
Robin I.
The price is €694
includes taxes & fees
19 Sept - 20 Sept
★ HostWise Stays ★ Tech Stay w/ In-Home Cinema & Secure Parking Spot
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 Pittsburgh Hotel Reviews

The Landing Hotel at Rivers Casino

The Landing Hotel at Rivers Casino

10/10 Excellent
"Everything was great and clean. The only issue was there was food left in our fridge. Other than that we had a great experience. Everyone was very friendly and we had a great time."
Angela 2-night trip
Posted 9 hours ago
The Landing Hotel at Rivers Casino

Find out more about Pittsburgh

Pittsburgh Holiday Homes information

Number of reviews
771
Accommodation
742 Holiday Homes
Lowest Price
€137
Highest Price
€694

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