Holiday houses in Shadyside

Cozy One-Bedroom East Side Apartment

Spacious and comfortable one-bedroom apartment centrally located in the East End (East Side) of Pittsburgh. Cozy bedroom, full kitchen, bathroom, living room, and dining area. Quiet neighborhood; close to restaurants, supermarkets, coffee shops, bars, East Liberty Transit Center. On bus lines for easy access around town. The apartment is also located on the bus line to Pittsburgh Paints Arena and is about a 20-minute drive to PNC Park and Heinz Field. Great for couples, solo travelers, LGBTQIA.

Shadyside Charm: Cozy Row Home Near Walnut Street

Beautifully maintained Shadyside row home, one block from Walnut Street, with bright open living spaces, updated appliances, and plenty of natural light. Walk to boutiques, cafes, and restaurants. Minutes to CMU, Pitt, and UPMC, with easy public transit access—ideal for campus visits, hospital stays, or weekend trips. Enjoy two off-street parking spots, a covered front porch, and a private deck. Finished basement features a 90” TV plus flexible space for an office, playroom, or cozy movie room.

Shadyside/Central @1 Spacious & Modern 1Bdr w/Prkg

Spacious and family oriented & Modern 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 bedroom, living room & dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

Cozy King Suite with Parking!

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 1BR/1 bath apartment in a prime location, with all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted & entirely remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances & in-unit laundry is brand new!

The Maverick by Kasa | Steps to Bakery Square

The Maverick by Kasa is your gateway to the best dining, shopping, attractions, and entertainment in Pittsburgh. Located in the historic former YMCA in the East Liberty neighborhood, our storied building seamlessly blends classic charm with modern comfort, featuring a stylish on-site bar lounge that’s perfect for starting or ending your night in the Steel City. Our tech-enabled rooms offer self check-in at 4pm, 24/7 guest support by text and a Virtual Front Desk accessed via mobile device.

New Lux King Suite | Free Parking+Gym | Near UPMC

✨ Welcome to our stylish and modern apartment in the heart of Shadyside! This fully furnished 1 bedroom suite features sleek décor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: 🔹 Fitness Center & Yoga Studio 🔹 Free Street Parking 🔹 Complimentary Coffee Station 🔹 Variety of Co-Working Spaces 🔹 Resident Clubroom with TV 🔹 Courtyard with BBQ & Ping Pong Table 🔹 EV Charging Station 🔹 On-Site Retail 🔹 Bike Storage Room

Highly Walkable | <10 Min to Shadyside Favs!

✨Bold, modern, & unmistakably Pittsburgh!✨ Our 3br/2ba home spans the 2nd & 3rd floors, wrapped in sleek black-and-gold style with plush furnishings, premium finishes, and smart home tech. Perfect for friends or couples, you’ll enjoy a fully stocked kitchen, lightning-fast Wi-Fi, and a coffee bar that rivals your favorite café. Just steps to Shadyside, East Liberty, & Bakery Square bars, restaurants, and coffee shops, too! With Chore-Free Checkout® so you can focus on fun, not chores.

Friendship Retreat~B | 1BR w/ Gourmet Kitchen

Enjoy a stylish first-floor 1BR with a gourmet kitchen featuring high-end appliances and a spacious living area perfect for relaxing or entertaining. The queen-size bedroom offers a comfortable night’s sleep. High-speed WiFi and a dedicated workspace make it ideal for business travelers or remote work. Access to shared parking (6 spots, first-come, first-served). Located near West Penn Hospital and UPMC Shadyside, perfect for couples, visiting families, or medical stays.

Parking+GYM+HULU+ Near Retail Shopping|UPMC|Dining

Welcome to your cozy Shadyside home away from home. Thoughtfully designed and perfectly located, this space invites you to slow down and settle in. Start your mornings with a coffee along Walnut Street, explore the neighborhood’s charming local shops, then come back to a place that feels familiar and relaxing. Whether you’re here for work, hospital visits, or a quick city escape, this is a warm, peaceful spot to recharge and enjoy the best of Pittsburgh.

StudioApt w/Gym+EV+Free Parking+Near Pitt Uni UPMC

Welcome to our stunning cozy 1-bed studio unit. Perfect for both business and leisure travelers, this elegant retreat offers a perfect blend of comfort, style, and convenience, ensuring a memorable stay in the heart of Pittsburgh. Nestled in a prime location, our unit provides easy access to the city’s top attractions, making it the ideal base for exploring everything Pittsburgh has to offer *ID and Background verification needed *

Sunny Friendship "Treehouse" 2 story / 1BD gem

Friendship Treehouse: Walking distance to 3 hospitals, our private, 2 story apartment w/ separate entry is steps away from great restaurants, coffee shops, yoga studios, art galleries & major bus lines. Located on a quiet tree-lined street in the aptly named Friendship area, we are an easy commute to Pitt & CMU. Our apartment is perfect for all of your travel & work needs. Suited for solo travelers, couples, and business travelers.

①min->Walnut:CMU:UPMC

I've hosted & co-hosted for 4 years. All questions are answered here so you can make an informed decision. ★ 3 min Walk to Walnut Street ★ 3 minutes Drive to UPMC Shadyside ★ 5 min Drive to CMU ★ 5 minutes Drive to Bakery Square ★ 6 minutes Drive to University of Pittsburgh ★ 8 min drive to Duquesne University ★ 10 min drive to Downtown ★ 15 min drive to Mount Washington We take absolute pleasure in welcoming you in our home.