
Vacation rentals in Shadyside
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Top-rated vacation rentals in Shadyside
Guests agree: these stays are highly rated for location, cleanliness, and more.

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

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.

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)

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.

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

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.

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.

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!

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.

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.

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).

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
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Other great vacation rentals in Shadyside

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

Luxurious 2Bed by Whole Foods

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

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

Spacious Double King bed Penthouse Suite

3 BR home|Steps from Walnut Street w/Free parking!

Cozy Apt in Heart of Shadyside - Private Balcony

SPACIOUS 1 BEDROOM APT IN PITTSBURGH (K1)
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$16,715 GYD | G$16,924 GYD | G$18,387 GYD | G$20,476 GYD | G$23,610 GYD | G$24,237 GYD | G$21,939 GYD | G$23,610 GYD | G$22,148 GYD | G$21,730 GYD | G$20,685 GYD | G$18,805 GYD |
| Avg. temp | -2°C | 0°C | 4°C | 11°C | 16°C | 21°C | 23°C | 22°C | 18°C | 12°C | 6°C | 1°C |
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!
Destinations to explore
- Fitness-friendly rentals Shadyside
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- Rentals with a patio Shadyside
- Family-friendly rentals Shadyside
- House rentals Shadyside
- Pet-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Apartment rentals Shadyside
- Rentals with a washer and dryer Shadyside
- Rentals with a fireplace Shadyside
- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Acrisure Stadium
- Idlewild & SoakZone
- Kennywood
- National Aviary
- Raccoon Creek State Park
- Point State Park
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Carnegie Museum of Art
- Schenley Park
- Children's Museum of Pittsburgh
- Randyland
- Senator John Heinz History Center
- Cathedral of Learning
- University Of Pittsburgh
- Carnegie Science Center
- David Lawrence Convention Center
- Petersen Events Center




