Vacation rentals in Shadyside

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Shadyside

Guests agree: these stays are highly rated for location, cleanliness, and more.

%{current} / %{total}1 / 1
Top guest favorite
The modern kitchen features sleek wood cabinetry and stainless steel appliances, including a microwave and dishwasher. A small dining area is visible through the glass door leading to a balcony. Essentials like a kettle and coffee maker are positioned on the countertop.
Apartment in Shadyside
4.99 out of 5 average rating, 73 reviews

GYM+HULU with Parking Near UPMC|Shopping|Pitt Uni

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: šŸš—FREE Street Parking for 1 Car(Based on Availability) šŸ‹šŸ»ā€ā™‚ļøState-Of-The-Art (24/7)Fitness Center šŸ’¼Private & Co-Working Spaces šŸ”ŒLevel 2 EV Charging Station Available šŸµComplimentary Tea/Coffee Station šŸ“Ping Pong Table, Comfy Seating Area šŸ–Outdoor BBQ 🐾Pet Friendly

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, 147 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 living room features a large television on a low stand, positioned across from a spacious sectional couch. Natural light enters through three windows, illuminating hardwood floors and indoor plants. A small round table is located in front of the couch, enhancing the inviting atmosphere.
Condo in Shadyside
4.98 out of 5 average rating, 45 reviews

Bright & sunny apt in Shadyside with free parking

Bright & sunny second-floor apartment located in the heart of Shadyside. Perfect for couples and professionals who are in Pittsburgh for just a week to a few months. Steep discount on month rentals. The apt is close to the restaurants & boutique shops on Walnut Street & Ellsworth. Whole Foods & Giant Eagle Market district is just down the street. If you like to cook, the kitchen is equipped w/ a new induction Samsung range with vented range hood, KitchenAid mixer, blender, and food processor.

Guest favorite
The open-concept living space exhibits a seamless flow from the kitchen to the dining area, featuring a large wooden table surrounded by contemporary chairs. Natural light fills the room, highlighting the dining area and the lush greenery visible through the sliding doors.
Apartment in Shadyside
4.96 out of 5 average rating, 25 reviews

Sunny Shadyside Condo with Private Garage

Peaceful and unique 2 bedroom, 2 bathroom loft style condo with sauna, soaking tub, private patio and garage. Located in Pittsburgh's iconic Shadyside neighborhood - just steps from Walnut Street, and some of Pittsburgh's best shopping and dining options. An 8 minute walk to UPMC Shadyside, and a 20 minute walk to Carnegie Mellon University, Bloomfield, and Friendship. Direct airport bus stops 3 blocks from house. Due to the layout of the condo, the space is not ideal for small children.

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, 284 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.

Guest favorite
A modern kitchen features white cabinetry and a striking black and white granite countertop. Stainless steel appliances, including a refrigerator and microwave, are complemented by a stylish faucet. The exposed brick wall adds character, while decorative plants offer a touch of greenery.
Apartment in Shadyside
4.91 out of 5 average rating, 270 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. ā­ļøSuper comfy queen memory foam mattress 🌟24/7 Guest support ā­ļøFree off-street parking! 🌟Fully stocked & equipped kitchen ā­ļøQueen sized pull out sofa 🌟Pet Friendly (Must provide vaccination records) ā­ļøLaundry (Free and in-unit)

Guest favorite
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.
Apartment in Shadyside
4.96 out of 5 average rating, 125 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.

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, 158 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.

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, 348 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. šŸŽˆSmart lock w/ private entrance šŸŽˆLuxurious waterfall shower head šŸŽˆprivate parking lot šŸŽˆFull equipped kitchen

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, 472 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).

Guest favorite
Apartment in Shadyside
4.85 out of 5 average rating, 40 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, 208 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. price€ 69€ 70€ 76€ 85€ 98€ 100€ 91€ 98€ 92€ 90€ 86€ 78
Avg. temp-2°C0°C4°C11°C16°C21°C23°C22°C18°C12°C6°C1°C

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 € 26 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!

  1. Airbnb
  2. United States
  3. Pennsylvania
  4. Allegheny County
  5. Pittsburgh
  6. Shadyside