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.

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Top guest favorite
The exterior entrance of the apartment is shown, featuring a short path lined with greenery. A wooden ramp leads up to the door, surrounded by various plants, creating a welcoming and natural entrance. The door is framed with a glass panel, allowing light to enter.
Apartment in East Liberty
4.97 out of 5 average rating, 148 reviews

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.

Top guest favorite
The exterior of a sunporch suite is displayed, featuring large wall-to-wall windows framed by white columns. A pathway leads to the entrance, surrounded by lush greenery, including a bush. The home showcases a charming blend of white and red brick, adding character to the facade.
Guest suite in Highland Park
4.98 out of 5 average rating, 288 reviews

Historic Sunporch Suite

Welcome! We are delighted to share with you our favorite room in an 1895 Georgian Colonial home. This comfortable sunporch suite is ideal for two guests or a family with a young child. Located in a safe, quiet, and wonderful section of Pittsburgh, we are close to the zoo and Children's Hospital, and a short drive from downtown. This suite has its own separate entrance, bathroom, and kitchenette. The wall-to-wall windows look over the front yard, courtyard, and our neighbor's Victorian home.

Top guest favorite
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.
Apartment in Shadyside
4.97 out of 5 average rating, 140 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!

Guest favorite
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.
Apartment in Shadyside
4.91 out of 5 average rating, 334 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!

Guest favorite
The living room features a large sectional couch in a neutral hue, positioned around a low coffee table. A window covered with vertical blinds allows natural light to enter, and an air conditioning unit is situated nearby. The floor has a wood-like finish, adding warmth to the space.
Apartment in Shadyside
4.77 out of 5 average rating, 582 reviews

Quaint cozy Shadyside One Bedroom

Cozy apartment located in Shadyside.Just steps away from Shadyside Hospital, this apartment is great for long or short term visitors.Grocery stores, restaurants, bars, and shops are all just a few minute walk from this apartment as well. The apartment is a short drive to Heinz Field, PPG Paints Arena, PNC Park, and all the amazing museums Pittsburgh has to offer! Also near by is CMU, PITT, Chatham Univeristy, and Carlow College.Free parking & WiFi.Towels,bed linens,toilet paper provided.

Guest favorite
A charming exterior view of a two-story Victorian home is displayed. The blue and green siding is complemented by a green door adorned with a wreath. A pathway leads to the entrance, flanked by wooden fences and natural greenery.
Apartment in Shadyside
4.89 out of 5 average rating, 123 reviews

Victorian home 2 bedroom Shadyside

Bright, sunny, spacious 2 bedroom apartment with 1 parking space in the heart of Shadyside. This apartment is in a Victorian home on a quiet street. There is a train that runs below the street I feel it is part of the history and charm of city living. Shopping, restaurants, UPMC hospitals, Universities, museums and cultural activities, within walking distance or public transportation. The unit has been recently updated, beautiful new bathroom and hardwood flooring through out.

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
4.9 out of 5 average rating, 10 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

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, 138 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
A spacious bed is positioned against a white wall, featuring neutral bedding and decorative pillows. Two modern bedside lamps provide soft lighting. To the left, a sleek sleeper sofa complements the minimalist design of the room.
Apartment in Friendship
4.84 out of 5 average rating, 250 reviews

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

This Bright basement studio is for anyone needing a stylish, clean place to stay while visiting Pittsburgh. It has a new queen bed, sleeper sofa, desk, bar and a very large bathroom. It has a private entrance at the back of a beautiful 1890s Pittsburgh mansion. It works very well for travelers 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
A bright kitchen space is shown, featuring modern cabinetry and stainless steel appliances. A central island with seating for four is highlighted, complemented by a stylish pendant light above. Natural light streams in through a nearby window, enhancing the clean, inviting atmosphere.
Apartment in Bloomfield
4.96 out of 5 average rating, 357 reviews

Cozy Entire APT B Friendship Park & Free Parking

Ground Floor Entire apartment with one bedroom, living room, bathroom is located in Bloomfield, a quiet yet vibrant neighborhood that’s central to all the best attractions. It features off Street parking , a rare find in the central city. This space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

Guest favorite
Apartment in Shadyside
4.87 out of 5 average rating, 45 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*

Top guest favorite
A cozy bedroom features a spacious bed dressed in an orange quilt. Two windows allow natural light to fill the room, and a colorful chair sits beside a small nightstand. A decorative fireplace adds character, complemented by framed artwork hanging above.
Guest suite in Bloomfield
4.98 out of 5 average rating, 213 reviews

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.

Popular amenities for Shadyside vacation rentals

When is the best time to visit Shadyside?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$16,737 GYDG$16,947 GYDG$18,411 GYDG$20,503 GYDG$23,642 GYDG$24,269 GYDG$21,968 GYDG$23,642 GYDG$22,177 GYDG$21,759 GYDG$20,713 GYDG$18,830 GYD
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Quick stats about vacation rentals in Shadyside

  • Total vacation rentals

    Explore 320 vacation rentals in Shadyside

  • Nightly prices starting at

    Shadyside vacation rentals start at G$6,277 GYD per night before taxes and fees

  • Verified guest reviews

    Over 27,330 verified reviews to help you choose

  • Family-friendly vacation rentals

    110 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 110 rentals that welcome pets

  • Rentals with dedicated workspaces

    250 properties have a dedicated workspace

  • Wi-Fi availability

    320 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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