
Holiday rentals in Shadyside
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Top-rated holiday rentals in Shadyside
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UPMC|Shopping+HULU Near Universities|PARKING+GYM
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: šFREE Street Parking for 1 Car(Based on Availability) šš»āāļøState-Of-The-Art (24/7)Fitness Center š¼Private & Co-Working Spaces šLevel 2 EV Charging Station Available šµComplimentary Tea/Coffee Station šPing Pong Table, Comfy Seating Area šOutdoor BBQ š¾Pet Friendly

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.

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.

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!

Private Room in Pittsburgh near Carnegie Mellon
Cozy private room in Squirrel Hill. The apartment is shared with myself and my roomate. We keep to ourselves as we are busy working, researching, and out of the house a lot in the evenings. However, we are here to answer any questions you may have about the house or the city of Pittsburgh! The private room includes: a microwave, mini refrigerator,Keurig and coffee pods, TV, Roku, a wardrobe,blackout curtains, desk, an adjustable bed, towels, & washcloths and an AC (excluding fall/winter).

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.

Lux King Bed | Free Parking + Gym | UPMC+CMU+Pitt
⨠Welcome to our stylish and modern studio apartment in the heart of Shadyside! This fully furnished suite features sleek dĆ©cor, a fully equipped kitchen, cozy living space and luxurious king bed. Enjoy top-tier amenities, including: š¹ Fitness Center & Yoga Studio š¹ Free Street Parking š¹ Complimentary Coffee Station š¹ Variety of Co-Working Spaces š¹ Resident Clubroom with TV š¹ Courtyard with BBQ & Ping Pong Table š¹ EV Charging Station š¹ On-Site Retail š¹ Bike Storage Room

Shadyside/Central @4 Stylish&Central Studio w/Prkg
Stylish and Central family oriented modern Studio apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment a Studio with bathroom, kitchen 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.

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.

Chic & Cozy 2BR | Walkable Shadyside Location
Fresh 2 BR apartment in the heart of Shadyside! Prime location, steps from UPMC Shadyside & Walnut Street! Fully equipped for either a long or short stay! šKing Bed (Memory foam mattress) āļøQueen Bed (Memory foam mattress) šPet friendly! āļøCentral AC/ Heat šFully stocked & equipped kitchen āļøLuxurious waterfall shower head šTwo Smart TVs āļøFree Street parking šLaundry (Shared & Free) āļøPull out bed (Full) š„Message today to secure your reservation!š„

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).

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 holiday rentals
Other great holiday rentals in Shadyside

Upscale 2BR suite ~ Free Parking & Walkable!

Cozy 2BR steps from Walnut St!

Upscale King Suite by WholeFoods

Shadyside/Pittsburgh, Modern&Accessible 2BD w/Prkg

Upscale King Bed Suite |ADA w/ Free parking!

Stunning 3BR Penthouse Suite| 2 decks| A+ Location

Upscale 2 BR Suite ~ Private deck & Walkable!

High End 3 King 2Bath Apt~Parking~Steps to Walnut!
Quick stats about holiday rentals in Shadyside
Total rentals
320 properties
Nightly prices starting at
Ā£22 before taxes and fees
Total number of reviews
27K reviews
Family-friendly rentals
110 properties are a good fit for families
Pet-friendly rentals
110 properties allow pets
Rentals with dedicated workspaces
250 properties have a dedicated workspace
Destinations to explore
- Fitness-friendly rentalsĀ Shadyside
- Rentals with an EV chargerĀ Shadyside
- Rentals with outdoor seatingĀ Shadyside
- Rentals with a patioĀ Shadyside
- Family-friendly rentalsĀ Shadyside
- Flat rentalsĀ Shadyside
- Rentals with a washing machine and dryerĀ Shadyside
- Rentals with a fireplaceĀ Shadyside
- Pet-friendly rentalsĀ Shadyside
- House rentalsĀ Shadyside
- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Ohiopyle State Park
- Oakmont Country Club
- Raccoon Creek State Park
- Kennywood
- Yellow Creek State Park
- National Aviary
- Phipps Conservatory and Botanical Gardens
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Point State Park
- Narcisi Winery
- Hidden Valley Resort
- Schenley Park
- Bella Terra Vineyards
- Senator John Heinz History Center
- Children's Museum of Pittsburgh
- Cathedral of Learning