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
Private room in Squirrel Hill South
4.86 out of 5 average rating, 645 reviews

Quiet room upstairs- wifi - parking- Squirrel Hill

Situated in the heart of Squirrel Hill with dining, theater, shopping and parks within a short safe walking distance. Explore the incredible variety of Chinese, Korean, Thai, Mexican, Jewish, Italian, Indian foods that reside in our neighborhood. CMU, Pitt, Chatham, Duquesne & Oakland are close by with bus stops just outside. Phipps Conservatory is a 7 min drive. Pittsburgh's famous Frick Park w/ endless trails is under a mile away. Schenley Park is under a 20 min walk past Pigeon Bagels 🥯

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, 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.

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, 26 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
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.
Flat 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 favourite
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.
Flat 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!

Top guest favourite
Private room in Squirrel Hill North
4.94 out of 5 average rating, 127 reviews

Private Room Near Carnegie Mellon University-Twin

Cozy private room in Squirrel Hill. Typically, the apartment is shared with 1 additional guest and a tenant. Host may pop up to clean the apartment/additional room during your stay. The private room includes: a twin bed, microwave, mini refrigerator, TV, Roku, portable desk, twin bed, towels, washcloths and an Air Conditioner. There is a cat on the property, but most times she will be in the tenant's room. You may not even see the cat. If allergic to cats, I would not book this listing.

Guest favourite
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.
Flat in Shadyside
4.77 out of 5 average rating, 581 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.

Superhost
Private room in North Oakland
4.86 out of 5 average rating, 167 reviews

Oakland/University @C Modern & Stylish Private Bd

Spacious & Modern private room close to Oakland, Shadyside, Bloomfield and Friendship, steps to Universities. A modern design features a king bed, shared bathroom, working desk. Free Street Parking is available and instructions to obtain a parking pass will be provided on check in date. Please check full listing description for more details and shared amenities. Walk to grocery store, restaurants, hospitals and universities. Perfect for savvy budget travellers who deserve quality stay.

Guest favourite
A modern bedroom is defined by a wooden bed frame featuring a cozy mattress, complemented by two nightstands with lamps. Wall art adds a touch of elegance, while a glimpse of the kitchen can be seen through the open door.
Flat in Shadyside
4.92 out of 5 average rating, 128 reviews

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

Stylish and Bright 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 favourite
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.
Flat 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

Top guest favourite
A cozy bedroom features a tufted headboard and a comfortable bed adorned with decorative pillows and a gray throw. Natural light filters through a large window with blinds, while a bedside table and stylish lamp complete the elegantly simple decor.
Flat in Shadyside
4.86 out of 5 average rating, 161 reviews

Shadyside apartments: 1 Bed-1 full BA Jewel!

Shadyside jewel! Spacious, stylish-&- chic! Conveniently located in the prime of Pittsburgh's favorite walkable neighborhood. Extraordinary comfortable interior with in-suite laundry & exclusive covered front porch! Eat-in or dine out. There are many near-by restaurants, quaint shops, unique restaurants & bars, beautiful city parks, culture-rich museums, state-of-the-art sports facilities, Universities, Hospitals. Super easy access to public transportation too!

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, 428 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).

Popular amenities for Shadyside holiday rentals

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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 £22 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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