Pittsburgh Vacation Homes

A cityscape with a river, bridges, and a red tram.

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Our top choices for Pittsburgh holiday homes

A modern kitchen with white cabinetry, a central island, and a dining area with a clear table.

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

North Side

Kelly D.

HK$2,249 total

includes taxes & fees

9 Nov - 10 Nov

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.

2. M&J - Emlin 513 St.

North Side

Gerrit v.

HK$1,786 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with wooden accents, a dining area with a table and chairs, and a gray sofa with patterned cushions.

3. Lovely Strip District loft with free parking

Strip District

M D.

HK$1,388 total

includes taxes & fees

5 Nov - 6 Nov

A living room with a fireplace, a sofa, a coffee table, and two paintings on the wall.

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

North Side

Alli S.

HK$1,517 total

includes taxes & fees

2 Dec - 3 Dec

A cozy living room with a brick fireplace, a wooden dining table, and a staircase.

5. Park Free★Amazing Space★Professionally Cleaned!

North Side

Jennifer Y.

HK$1,756 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with a sofa, two armchairs, a coffee table, and a fireplace.

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

North Side

helena w.

HK$1,346 total

includes taxes & fees

9 Nov - 10 Nov

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

7. Explore Pittsburgh from a Modern, Hip Bungalow

North Side

Yukiko M.

HK$1,398 total

includes taxes & fees

15 Nov - 16 Nov

Architectural staircase leading to bright, open living spaces

8. ★ HostWise Stays ★ Spacious Stay in Prime Location | Theater & Patio

North Side

Melanie F.

HK$2,603 total

includes taxes & fees

29 Nov - 30 Nov

A kitchen with a brick wall, stainless steel appliances, a yellow door, and a sliding barn door.

9. ★ HostWise Stays ★ King Bed Carriage House in Mexican War Streets

North Side

Eva S.

HK$1,654 total

includes taxes & fees

5 Nov - 6 Nov

A living room with a fireplace, a television, and a dining area with a table and chairs.

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

South Side Flats

Butch K.

HK$1,609 total

includes taxes & fees

5 Nov - 6 Nov

A living room with a fireplace, a flat-screen TV, a sofa, and a coffee table.

11. 1 BEDROOM APT IN PITTSBURGH (F) -Friendship Area

Bloomfield

Lisa K.

HK$1,340 total

includes taxes & fees

5 Nov - 6 Nov

A compact kitchen with a white door, grey cabinets, a sink, and a wooden countertop.

12. Cozy escape close to downtown, stadiums & parks

North Side

Jennifer B.

HK$1,451 total

includes taxes & fees

16 Nov - 17 Nov

A modern living room with a wooden bench, a sofa, a coffee table, and a painting on the wall.

13. Updated & Comfy Bungalow with Parking! Easy Access

Duquesne Heights

Brody W.

HK$1,940 total

includes taxes & fees

14 Nov - 15 Nov

A modern living room with a fireplace, a staircase, and a view of the outdoors.

14. 1207 Ocala - Boat House - North Side

North Side

Edward C.

HK$2,190 total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with dark wooden cabinets, a central island with bar stools, a stainless steel refrigerator, and a pendant light above the island.

15. ★ HostWise Stays ★ Retro-vibes home, just minutes from stadiums!

North Side

Cait A.

HK$2,414 total

includes taxes & fees

30 Nov - 1 Dec

A kitchen with wooden cabinets, a stainless steel refrigerator, a countertop, and a sliding glass door leading to a balcony.

16. Urban Retreat with Garage on Mt. Washington

Mount Washington

James S.

HK$1,526 total

includes taxes & fees

9 Nov - 10 Nov

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

North Side

Jason S.

HK$2,883 total

includes taxes & fees

5 Nov - 6 Nov

A modern kitchen with a central island, stainless steel appliances, and a seating area with a sofa and coffee table.

18. Not so tiny house with full kitchen & patio swing

Garfield

Anna B.

HK$1,388 total

includes taxes & fees

5 Nov - 6 Nov

A modern living room with a sofa, ottomans, a coffee table, and a ceiling fan.

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

North Side

Brian G.

HK$2,641 total

includes taxes & fees

30 Nov - 1 Dec

A living room with a green sofa, a coffee table, and a chair. There is a coat rack and a television on the wall.

20. 1210 James St. #1 ★Pro Cleaned

North Side

Donna Huntermark L.

HK$1,621 total

includes taxes & fees

8 Nov - 9 Nov

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Top Pittsburgh Hotel Reviews

DoubleTree by Hilton Pittsburgh - Green Tree

10/10 Excellent

"Lean room, friendly staff"

The Landing Hotel at Rivers Casino

10/10 Excellent

"All of the staff was excellent with a couple minor hickups... one being one of the Breakfast attendants, was not very polite when another couple was trying to make kind morning greetings!!!! The other was the bartender in the hotel wasn't very nice when the drink that was ordered was completely wrong!!! The room was clean and comfortable and had lots of fun in the casino"

Kimpton Hotel Monaco Pittsburgh by IHG

8/10 Good

"Public areas and private rooms are very clean. Staff were friendly but not always readily available, especially the Valet Parking team. Had to call for additional towels, as only 1 was provided originally by housekeeping. Only 1 restaurant and required reservations if you didn't want to wait 30-45 mins for a table."

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