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.

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Top guest favourite
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.
Flat in East Liberty
4.97 out of 5 average rating, 146 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.

Guest favourite
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.
Flat in Shadyside
4.96 out of 5 average rating, 24 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 favourite
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.

Top guest favourite
A brick townhouse features a charming facade with multiple gabled roofs and evenly spaced windows. The entrance is accented by a wooden porch, surrounded by trees and landscaping that complement the residential setting.
Home in Shadyside
5 out of 5 average rating, 64 reviews

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!

Guest favourite
Private room in Squirrel Hill North
4.94 out of 5 average rating, 136 reviews

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).

Guest favourite
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.
Flat 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. ⭐️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)

Superhost
A spacious sleeping area is highlighted by a wooden bed with neutral bedding. A cozy fireplace is located beneath a clock, accompanied by a decorative plant and a circular seating area. Natural light enters through the windows, enhancing the room’s bright atmosphere.
Flat in Shadyside
4.92 out of 5 average rating, 125 reviews

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.

Guest favourite
A spacious living area features a comfortable gray sofa set and a small coffee table. A mounted flat-screen TV is visible on one wall, while a kitchenette with modern appliances is positioned adjacent to it, highlighted by natural light from a nearby window.
Guest suite in Friendship
4.89 out of 5 average rating, 422 reviews

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).

Top guest favourite
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.

Guest favourite
Flat in Bloomfield
4.92 out of 5 average rating, 314 reviews

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.

Guest favourite
A spacious bedroom is equipped with a queen bed covered in a light blue duvet. Natural light filters through the window with sheer curtains, illuminating a small desk and chair. A cozy couch with a patterned design completes the inviting space.
Private room in Shadyside
4.94 out of 5 average rating, 105 reviews

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.

Top guest favourite
A spacious living area features a large sectional sofa adorned with a textured throw, complemented by a wooden coffee table. A 70-inch smart TV is mounted on the wall, while a small decorative plant and a cozy chair add a touch of warmth to the space.
Flat in Shadyside
4.96 out of 5 average rating, 162 reviews

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

When is the best time to visit Shadyside?

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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
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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!

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