
Holiday rentals in Herrs Island
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Top-rated holiday rentals in Herrs Island
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Walk River Path to ‘26 NFL Draft *FREE Parking*
🏈 THE 2026 NFL DRAFT 🏈 Step out your front door onto Three Rivers Heritage Trail & walk to Acrisure Stadium!! Luxury 2200 sq ft 2-bed, 2.5-bath townhouse on the Allegheny River island of Washington's Landing. Water views. Parklike, modern, spacious, well-equipped, and close to downtown Pittsburgh. Walk or bike to the Strip District and beyond. Two outdoor decks. 10 new pickleball courts on the island. Stroll past the boat docks to Redfin Blues (in spring & summer) for happy hour or a boat ride

Pittsburgh, PA - North Side
Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

Cozy warm room in lovely Squirrel Hill
Situated in the heart of Squirrel Hill, all sorts of dining, theater, shopping and parks are within a short safe walking distance. Explore the incredible variety of Chinese, Korean, Mexican, Jewish, Italian, Indian foods that reside in our neighborhood. CMU, Pitt, Chatham, Duquesne & Oakland are close by bus. Frick Park w/ endless trails is under a mile away. Phipps Conservatory & Schenley Park are a 7 min drive. Just over 10 min drive to The Strip, Mount Washington, Monongahela Incline.

Allegheny River Aqua Villa
Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Phenom cozy ROOM ctrl to DT, UPMC, Oakland, Bkr Sq
Peaceful cozy den w kitchenette. Shared kitchen bath 17 min downtown, UPMC, or Bakery Sq Off rt 28 & Highland Pk Br. Minutes to Waterworks BUS 91 & 1. Econ for YOUNG guests Nice bed, TV, desk, window, petite comfy 93 sqft room. Fast WiFi Safe neigb In a boro as part of a prominent suburban school district. Above a gift shop, w/ sweet free off-street parking. Laundry. Quiet 2nd fl for best refreshment; Kitchen on 1st 50+yr bldg. Old biz/res st Riverview on the same street, 5 min walk.tte

Quiet Private Room
This Private Room is in the SECOND LEVEL of a townhouse that has OTHER ROOMS for rent via Airbnb. It’s located in a very quiet and safe neighborhood in the Town of McCandless, about a 25-minute drive from downtown Pittsburgh. This place is an ideal base for those looking to sleep, shower and relax, while spending most of their time away from home, working or exploring our city and its surroundings. If you are looking for a comfortable, quiet, clean and homy place to stay, this is your place.

Private Room Near Carnegie Mellon University-Twin
Cozy private room in Squirrel Hill. Typically, the apartment is shared with 1 additional guest and a tenant. Host may pop up to clean the apartment/additional room during your stay. The private room includes: a twin bed, microwave, mini refrigerator, TV, Roku, portable desk, twin bed, towels, washcloths and an Air Conditioner. There is a cat on the property, but most times she will be in the tenant's room. You may not even see the cat. If allergic to cats, I would not book this listing.

Oakland/University @B Quiet & Stylish Private Bd
Cozy and Stylish private room close to Oakland, Shadyside, Bloomfield and Friendship, steps to Universities. A modern design features a queen bed, shared bathroom, working desk. Free Street Parking is available and instructions to obtain a parking pass will be provided on check in date. Please check full listing description for more details and shared amenities. Walk to grocery store, restaurants, hospitals and universities. Perfect for savvy budget travellers who deserve quality stay.

Cozy home in Spring Hill with a Single bedroom.
I do live here too, so welcome! My home is in a quiet neighborhood, walking distance to a park. I have a lot of natural light, a back deck with a serine view of Pittsburgh neighborhoods and the sunrise. The home is eclectically decorated. Your bedroom is a bit more calmly decorated with the same view as the deck and the morning sun. Located minutes from the Point, downtown's cultural distric, museums, the strip district and even closer to the Stadiums (both PNC Park and Heinz Field).

Brand New! Lawrenceville KING Suite - Huge Balcony
1 bedroom 1 bath apartment w/ a HUGE private balcony steps from Butler St in Lawrenceville neighborhood! Sleeper Sofa and extra linens for bigger groups. BRAND NEW construction! Enjoy this stylish space in the coolest neighborhood in town, steps to dozens of restaurants, shops, coffee shops. A few blocks to UPMC Children's hospital and the Strip District, short drive to Downtown, North Shore, Shadyside, Oakland, very close to Pitt, CMU, & several hospitals! Book your stay today!

Fenced Yard 3 Bd KING BED Home
Cozy and Central! Minutes to the Strip, Downtown & Stadiums. PET FRIENDLY 3-bd, 1-ba home is the perfect blend of modern amenities, welcoming vibes, and pet-friendly accommodations. Inside, you’ll find three bedrooms, a sophisticated bathroom, and an open-concept living area that’s ideal for lounging. The fully-equipped eat in kitchen features sleek appliances. Step outside to discover the real highlight—a fully fenced in double (city) lot that offers a space for your pets to roam.

Private Hot Tub | King Bd | Workspace | Kids Okay!
Soak, work, and relax at this vibrant Lawrenceville retreat! Enjoy your private hot tub on the patio, unwind in our colorful, fun interior, and make use of the flexible layout (1BR plus separate office / kid's room / treadmill desk workspace). It’s ideal for weekend escapes as well as extended stays, given the king bed! Enjoy the highly walkable location near top restaurants, bars, & coffee spots, unwind in the fenced patio, or kick back with smart TVs and a well stocked kitchen.
Popular amenities for Herrs Island holiday rentals
Other great holiday rentals in Herrs Island

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Destinations to explore
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- PNC Park
- Strip District
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Raccoon Creek State Park
- Kennywood
- National Aviary
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Narcisi Winery
- Schenley Park
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Bella Terra Vineyards
- Cathedral of Learning
- Reserve Run Golf Course
- Laurel Mountain Ski Resort




