Vacation rentals in Shadyside

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Top-rated vacation rentals in Shadyside

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Guest favorite
Apartment in Shadyside
4.88 out of 5 average rating, 58 reviews

HULU+GYM+PARKINGNear Universities|Shopping|UPMC

Discover comfort and convenience in our charming city haven. Perfect for professionals and travelers, our apartment is your gateway to nearby dining, boutique stores, shopping outlets, & attractions. Building amenities include: 🏋🏻‍♂️State-Of-The-Art (24/7)Fitness Center 💼Private & Co-Working Spaces 🚗FREE Street Parking for 1 Car(Based on Availability) 🍵Complimentary Tea/Coffee Station 🔌Level 2 EV Charging Station Available 🏓Ping Pong Table, Comfy Seating Area 🐾Pet Friendly 🍖Outdoor BBQ

Guest favorite
A living space is presented with a neutral color palette. A couch and chair are arranged around a small coffee table. A dining area with a table and four chairs is visible in the background. Natural light filters through vertical blinds on a nearby window, illuminating the space.
Apartment in Shadyside
4.78 out of 5 average rating, 693 reviews

Sunny Spacious Shadyside 1 bedroom

Bright one bedroom apartment can sleep up to three.Centrally located and just steps from Shadyside Hospital.The apartment offers guests easy access to numerous attractions, museums, stadiums, and concert venues.Just a few minutes walk to bars, restaurants, grocery stores, and shopping.This quaint apartment is perfect for a short or long term stay.Designated parking space makes it easy for you to come and go as you please.Fully equipped kitchen.Public transportation and rentable bikes close by.

Guest favorite
A modern living room features a comfortable sofa with decorative pillows, complemented by an armchair and a coffee table. The kitchen area showcases a marble countertop, with bar stools provided for dining. Bright wall art enhances the space, illuminated by natural light from the window.
Apartment in Shadyside
4.91 out of 5 average rating, 278 reviews

Queen Bed Suite|Heart of Shadyside|Walkable &Quiet

Stylish and freshly renovated 1 BR/ 1 bath apartment 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. ⭐️Super comfy queen memory foam mattress 🌟24/7 Guest support ⭐️Free off-street parking! 🌟Fully stocked & equipped kitchen ⭐️Queen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ⭐️Laundry (Free and in-unit)

Guest favorite
Home in Shadyside
5 out of 5 average rating, 11 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.

Guest favorite
A cozy bedroom features a spacious bed draped in a soft, natural-toned coverlet. A vintage mirror and wooden dresser are positioned against a brick wall. Natural light filters through a stained glass window, illuminating plants nearby. A glimpse of the bathroom is visible in the background.
Apartment in Shadyside
4.92 out of 5 average rating, 13 reviews

A Home In The Heart of Shadyside

Cozy 1 bedroom home steps from Walnut St. It's a little bit rough and a little bit refined (it's our latest work in progress). Its our home and we travel a lot, so we love to share our space with others. Walker's paradise; and very bike-able, with city bikes a block away. AC and heating. * Quiet, safe, and beautiful tree-lined streets * Carnegie Mellon University and East liberty- 6 min by bicycle * University of Pittsburgh - 9 min by bicycle * Shared courtyard and front porch

Top guest favorite
A cozy living area features a tan leather sofa adorned with decorative pillows, positioned in front of a modern electric fireplace. A rustic coffee table made from wood and a striped rug add warmth. In the background, a glimpse of the kitchen and dining space is visible.
Home in Lower Lawrenceville
5 out of 5 average rating, 18 reviews

Prime Location | 2 Parking Spaces | Luxury Home

You will love this home from the moment you lay eyes on inviting front porch featuring modern siding and the custom designed and built sturdy white oak door. This light-filled, open concept 3 bedroom and 2.5 bathroom home is the ideal short term housing for busy professionals such as physicians, business executives, professors, and families who are looking for a quiet oasis to rest and recharge, but still be close to hospitals, downtown, and in the heart of trendy Lawrenceville.

Guest favorite
A bedroom features a wooden bed with a neatly arranged striped comforter. Neutral-toned artwork adorns the wall above the bed. Soft lighting from a bedside lamp provides illumination, and a doorway leads to a bright, airy space beyond.
Apartment in Shadyside
4.93 out of 5 average rating, 149 reviews

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg

Stylish 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 & 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.

Guest favorite
The living area features a cozy couch with a decorative throw, providing a warm contrast to the exposed brick wall. A dining area with two stools is situated near the kitchen, while a large smart TV displays various streaming options.
Apartment in Shadyside
4.93 out of 5 average rating, 248 reviews

Chic Shadyside Apt w/ Balcony-1Block to Walnut St!

In the heart of Shadyside! 1 Block to Walnut St Short Walk to UPMC & West Penn hospitals, CMU & Pitt! 1BR/1 bath apartment with private covered balcony w/ TV in a prime location, dozens of restaurants, shops, coffee shops, and fitness studios close by. The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Free laundry included inside the unit. Fully stocked for both long and short term stays!

Top guest favorite
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.
Apartment in Shadyside
4.99 out of 5 average rating, 160 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.

Guest favorite
A spacious living area features a brown sofa and a glass coffee table, creating a relaxed seating space. A black mantel surrounds the television, while two dining chairs and a table are positioned nearby. Natural light filters in through the large windows, illuminating the wood floors.
Apartment in Shadyside
4.9 out of 5 average rating, 29 reviews

Studio on 5th Ave 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.

Guest favorite
A modern kitchen area features sleek cabinetry alongside a wooden countertop and stainless-steel appliances. A spacious gray sofa with decorative pillows is situated nearby, providing a comfortable seating option. Light streams through a window, illuminating the tiled floor and brick accent wall.
Apartment in Friendship
4.9 out of 5 average rating, 479 reviews

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

This Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, a new sleeper sofa, a full kitchen and a full bathroom with a private entrance on the 2rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

Top guest favorite
Apartment in Shadyside
4.88 out of 5 average rating, 51 reviews

Cozy Apt+Gym+ EV+Free Onsite Parking+Near UPMC

Welcome to our stunning luxury 1-bed studio unit. Perfect for both business and leisure travellers, 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 *

Popular amenities for Shadyside vacation rentals

When is the best time to visit Shadyside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,715 GYDG$16,924 GYDG$18,387 GYDG$20,476 GYDG$23,610 GYDG$24,237 GYDG$21,939 GYDG$23,610 GYDG$22,148 GYDG$21,730 GYDG$20,685 GYDG$18,805 GYD
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Quick stats about vacation rentals in Shadyside

  • Total vacation rentals

    Explore 350 vacation rentals in Shadyside

  • Nightly prices starting at

    Shadyside vacation rentals start at G$6,268 GYD per night before taxes and fees

  • Verified guest reviews

    Over 29,750 verified reviews to help you choose

  • Family-friendly vacation rentals

    120 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 120 rentals that welcome pets

  • Rentals with dedicated workspaces

    270 properties have a dedicated workspace

  • Wi-Fi availability

    350 of Shadyside vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Shadyside rentals

  • 4.9 Average rating

    Shadyside stays are highly rated by guests—averaging 4.9 out of 5!

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