Vacation rentals in Shadyside

An open living space features a modern kitchen with stainless steel appliances, a dining area with two stools, and a cozy seating arrangement with a brown couch and decorative pillows. A large window allows natural light to fill the area, complemented by sleek laminate flooring.

4.94 out of 5 average rating, 190 reviews

Cozy King Suite Just off Walnut

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!

A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.

4.98 out of 5 average rating, 111 reviews

Avant-Garde Escape by Walnut

Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

A fully equipped kitchen features modern white cabinetry, sleek granite countertops, and stainless steel appliances, including a microwave and stove. A double-basin sink is positioned near the window, with essential kitchenware, plates, and glassware arranged on the counter.

4.91 out of 5 average rating, 375 reviews

Upscale Double King Bed Suite ~ Steps from Walnut!

Upscale 2 bedroom/ 1 bathroom APT perfectly located in the heart of Shadyside where you can easily walk to plenty of bars, restaurants, shops and more! Fully equipped for an extended stay, weekend getaway, or just a place to crash for the night. ⭐️Two Memory foam king beds 🌟24/7 Guest Support ⭐️In-unt Washer/ Dryer 🌟Fully stocked & equipped kitchen ⭐️Sleeper sofa (Full) 🌟Pet Friendly (Most provide vaccination records) ⭐️Private entrance & front porch ⭐️Steps from popular Walnut Street!

5.0 out of 5 average rating, 17 reviews

Shadyside 2 BR | Walk to Walnut + On site parking

Bright, energizing and charming 2 BDRM Shadyside apartment in Pittsburgh's most walkable neighborhood. Steps from Walnut Street's best restaurants, cafés, and boutique shops. New furniture & furnishings (work/study, too), bed 'n bath, lighting, fully equipped kitchen (even an air fryer), fast Wi-Fi, 65" TV, in-unit washer/dryer & more. Smart self-check-in, with rare off-street reserved parking (for 1 Car; also: buses nearby). Minutes to Downtown, CMU, and Pitt — your perfect in-city stay.

4.96 out of 5 average rating, 25 reviews

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.

5.0 out of 5 average rating, 36 reviews

Shadyside Home - Walk to Walnut St - Free Parking

Beautifully maintained Shadyside row home one block from Walnut Street - and no cleaning fee. Bright, open living spaces, updated appliances, lots of natural light, yet quiet inside. Walk to boutiques, cafes, and restaurants; minutes to CMU, Pitt, and UPMC - ideal for campus visits, hospital stays, or weekend trips. Two off-street parking spots, a covered front porch, and a private deck. Finished basement adds a 90" TV plus flexible space for an office, playroom, or cozy movie room.

Apartment in East Liberty

4.97 out of 5 average rating, 34 reviews

Marble Bath Penthouse: King Bed, Laundry, Parking

Friendship Penthouse: Spacious 1-Bedroom/2-Beds, King + Sleeper Sofa, In-Unit Laundry & Free Parking. Recently renovated Victorian penthouse (3rd floor, no elevator) perfect for medical travelers, university visitors, students, and extended stays. Superhost with 4.97★ rating from 34 reviews. Steps from Whole Foods, Shadyside restaurants, UPMC Shadyside; short car ride to Carnegie Mellon & Pitt. Walkable historic neighborhood with genuine character, and free parking in Pittsburgh.

5.0 out of 5 average rating, 17 reviews

King Bed | Free Parking | Gym | UPMC, Pitt & CMU

✨ Welcome to our large, stylish studio in the heart of Shadyside! This modern, fully furnished suite features sleek décor, a fully equipped kitchen, a cozy living space, and a 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

A modern living area features a light grey sectional sofa draped with a vibrant orange throw. Colorful artwork adorns the wall above a sleek television, while a spiral staircase provides access to the upper levels. A dining area with pink chairs is visible in the background.

4.99 out of 5 average rating, 168 reviews

East End Penthouse in Shadyside w/rooftop deck

Modern and full of art, color, and light. A private spot to be inspired, reflect, write and or daydream.This luxury and unique 2 bedrooms, 3-level apartment is above a family home in the Shadyside/East End area. It is on a quiet residential street w/ ample outdoor space to conference and work from home. It has its own stunning private rooftop space,open floor plan, a true oasis in the city! Walkable to many local coffee/bars, gyms, shops and eateries in East Shadyside.

The spacious bedroom features a wooden platform bed with a plush mattress and white linens, complemented by a decorative blanket. A minimalist bedside table holds a lamp, while two framed botanical prints adorn the wall. Natural light filters through the window, enhancing the inviting atmosphere.

4.94 out of 5 average rating, 192 reviews

Shadyside/Pittsburgh, Modern & Cozy 1BD w/Prkng

Modern and family oriented 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 & 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.

A spacious living room is highlighted by a comfortable sofa with decorative pillows and a wooden coffee table. Elegant windows allow natural light to brighten the space, complemented by a flat-screen TV and a decorative fireplace. A cozy armchair enhances the inviting atmosphere.

4.94 out of 5 average rating, 32 reviews

Spacious 1 bd in Shadyside - Walk to CMU and Pitt

Welcome to Shadyside STAY, your cozy home base in Pittsburgh’s most walkable neighborhood. Just steps from Walnut Street’s coffee shops and boutiques, and minutes from CMU, Pitt, and UPMC Shadyside. CMU’s free shuttle stops right outside, making campus access effortless. Perfect for students, professors, young professionals and visiting parents, this bright, fully furnished studio blends modern comfort with a welcoming vibe, the ideal spot to work, study, and relax.