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Unique Group Stays in Pittsburgh

Theme: Unique Group Stays in Pittsburgh

Group Haven | Two Homes, Dual Rooftops & BBQ Fun

Rooftop Sauna + Hot Tub | Spa Room | Cabana!

Rooftop Deck & Fire Pit Haven Near Attractions

Rooftop Deck | Garage | Balcony Views | Upscale!

Squirrel Hill Oasis, Piano, Patio, BBQ, Parking

Sleeps 16 | Arcade | Huge Home | Park Free

Historic Gem | Soaking Tub • Fire Pit • EV Charger

3 Apts - 1 Listing! Great for groups! North Side!

Entire Apt. Building | 3 Units / 6BR | Park Free

Stylish Homes with Rooftop Decks, BBQ & Parking

Hot Tub | 5br | Parking | Deck | Amenities Galore!

Game Room & Hot Tub Getaway - Prime Grandview Spot

Luxury Rooftop & Theater Haven in Trendy Spot

Sleeps 12 in 3 Private Apts! | Mexican War Streets

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Don't take our word for it - trust the 14744 reviews from our guests.

Mathew

We had a wonderful experience staying at Chad’s place. He was a great host—friendly, responsive, and very accommodating throughout our stay. The property was clean, comfortable, and exactly as described.<br/>Chad made the whole process easy and was always available whenever we had a question. We truly appreciated his hospitality and would be happy to stay at his property again. We highly recommend Chad as a host!

Raiza

We stayed in September 2026. We had 8 adults and the house worked perfectly.  There are two bedrooms and a bath on the ground/basement level where you park. The main floor (or 2nd floor from back parking) is the living, dining, kitchen & powder room, then on 3rd level is two bedrooms and a full bath and top level (attic) was another full bedroom and bathroom. All the rooms had king beds and the bedding was wonderful!! We all loved the down alternative comforters so much we all purchased one! So soft, cooling and felt like a marshmallow!! We never ran out of hot water which with 8 ppl is no small feat in an older house. Whole home was well equipped with charger outlets on bedside tables. Very comfortable. Walked to Yinz coffee every morning. You do hear helicopters for the hospital but it didn’t bother us. Parking is tight but we fit 2 cars, just have to be careful pulling in and out. All in all would highly recommend!!

Sharon

Great stay! Excellent for a big group of people wanting to stay closer to the city. All the rooms were very nice and the rooftop was great. Would 100% stay here again.

Sydney Heintzinger

Chad’s place was very well appointed: newly renovated spaces, perfectly clean, spacious and open gathering areas, modern kitchen, and comfortable bedrooms. Our only wish was that the loft bedroom space was more private, but we knew that going in. Chad was very responsive and professional, and even got us an extra pack and play for our stay. Highly recommend

Anne

What Our Guests Have To Say

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The founders of HostWise have spent their careers on the road, and we know what it takes for a comfy stay. We want you to tell your friends about us! Though each one of our custom-designed properties is unique, we require the same base set of market-leading amenities & standards. No matter which HostWise property you choose, you’ll have confidence that you’ll always have consistent amenities, service, and seamless experiences. Walk in and say woah!