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

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.

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.

Avant-Garde Escape by Walnut
Welcome to our stylish, newly-renovated home, complete with modern amenities, tasteful decor, and all-new everything. Perfectly located just steps from Walnut Street’s best restaurants, bars, and shops—a prime base for exploring Pittsburgh! ⭐ 2 King beds + 2 Queen beds + 5 rollaway beds or futons - can sleep 16 easily! ⭐ Private deck ⭐ Free Washer/Dryer ⭐ 2 Off-Street Parking spaces (Free) ⭐ Pack N Play & High Chair Our team is here 24/7 to support you before, during, and after your stay!

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).

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)

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.

PRIVATE MINI STUDIO (D1)
This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd 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.

Cozy Entire AptA 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. The apartment was recently updated and feels fresh, spacious. This first floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

Shadyside Private Bed/Bath, Office, Free Parking
Heart of Shadyside - short walk to Walnut Street or Shadyside Hospital. One block to bus stop, grocery store, restaurants. Comfortable spacious bedroom with queen bed in townhome. Private bathroom with shower stall. TV, wifi, microwave, mini-fridge, coffee maker, dresser, large closet. Access to washer/dryer. Small desk and office chair. Additional loft workspace with docking station. Driveway parking.

Shadyside King Suite w/ Parking!
Stylish 1BR/1 bath apartment with off street parking in the heart of Shadyside, steps to Walnut St -- DESIGNATED OFF STREET PARKING! Short Walk to UPMC & West Penn hospitals, close to CMU & Pitt! The building was gutted and entirely remodeled, everything down to the soundproofing and top of the line appliances are brand new! Granite kitchen, Free laundry included inside the unit, 70inch 4K TV!
Popular amenities for Shadyside holiday rentals
Other great holiday rentals in Shadyside

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

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

Shadyside 2Bed 2Bath w/ Parking!

Bright & Upscale|King Bed|Free Parking w/Workspace

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

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

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

Stunning 2 BR King Bed Suite ~ Steps from Walnut
When is the best time to visit Shadyside?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $104 SGD | $105 SGD | $115 SGD | $128 SGD | $147 SGD | $151 SGD | $137 SGD | $147 SGD | $138 SGD | $135 SGD | $129 SGD | $117 SGD |
| 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 holiday rentals in Shadyside

Total holiday rentals
Explore 320 holiday rentals in Shadyside

Nightly prices starting at
Shadyside holiday rentals start at $39 SGD per night before taxes and fees

Verified guest reviews
Over 27,330 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 110 rentals that welcome pets

Rentals with dedicated workspaces
250 properties have a dedicated workspace

Wifi availability
320 of Shadyside holiday rentals include wifi 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
- Rentals with a washing machine and dryer Shadyside
- Pet-friendly rentals Shadyside
- Rentals with a fireplace Shadyside
- Rentals with a patio Shadyside
- Flat rentals Shadyside
- Fitness-friendly rentals Shadyside
- Rentals with an EV charger Shadyside
- Rentals with outdoor seating Shadyside
- House rentals Shadyside
- Family-friendly rentals Shadyside
- PNC Park
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Raccoon Creek State Park
- Kennywood
- Yellow Creek State Park
- National Aviary
- Ohiopyle State Park
- Fox Chapel Golf Club
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Carnegie Museum of Art
- Narcisi Winery
- Schenley Park
- Senator John Heinz History Center
- Bella Terra Vineyards
- Children's Museum of Pittsburgh
- Cathedral of Learning
- Laurel Mountain Ski Resort




