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
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, 70 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!

Top guest favourite
Private room in Squirrel Hill North
4.94 out of 5 average rating, 139 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 cozy living area is presented with a charcoal gray sofa facing a wall-mounted smart TV. Natural light filters through two large windows adorned with blue curtains. A white coffee table sits on a patterned area rug, complemented by an armchair and a green plant nearby.
Flat in Shadyside
4.89 out of 5 average rating, 151 reviews

Cozy King Suite|Central, Workspace + Free Parking

Enjoy our spacious king-sized bed suite located in the friendly Friendship/ Shadyside neighborhood. This newly renovated retreat is just a short distance from all that Pittsburgh has to offer! Steps away from Pittsburgh's Favorite local coffee shop - Yinz Coffee! 💫 King bed (Memory foam mattress) 💫 Sleeper Sofa (Queen) 💫 Free in-unit washer/ dryer 💫 Large L-Shaped desk w/ fast wifi 💫 Pet-friendly 💫 24/7 Guest support 💫 Free off-street parking - 1 vehicle 💫 Close to CMU / Pitt!

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
The private room features a wooden bed frame with a soft grey blanket laid over the queen bed. Natural light illuminates the space from a nearby lamp. Two framed botanical prints hang above the nightstand. A sleek white chair and desk are visible in the corner.
Private room in North Oakland
4.95 out of 5 average rating, 184 reviews

Oakland/University @B Quiet & Stylish Private Bd

Cozy and Stylish private room close to Oakland, Shadyside, Bloomfield and Friendship, steps to Universities. A modern design features a queen 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 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

Guest favourite
A bedroom features a wooden bed with a neatly arranged striped comforter. Neutral-toned artwork adorns the wall above the bed. Soft lighting from a bedside lamp provides illumination, and a doorway leads to a bright, airy space beyond.
Flat in Shadyside
4.93 out of 5 average rating, 137 reviews

Shadyside/Pittsburgh, Modern & Stylish 1BD, w/Prkg

Stylish and 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 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, 159 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!

Top guest favourite
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.
Flat in Bloomfield
4.96 out of 5 average rating, 356 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. 🎈Smart lock w/ private entrance 🎈Luxurious waterfall shower head 🎈private parking lot 🎈Full equipped kitchen

Guest favourite
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.
Flat 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 favourite
Flat in Shadyside
4.92 out of 5 average rating, 51 reviews

StudioApt W/Gym+EV+Free Parking+Near Pitt Uni UPMC

Welcome to our stunning cozy 1-bed studio unit. Perfect for both business and leisure travelers, 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 *

Guest favourite
An open-concept living area features a modern kitchen with white cabinetry and granite countertops. A comfortable sofa sits in front of a coffee table, while a mounted flat-screen television displays various streaming options. Soft lighting is provided by a ceiling fan and recessed lighting.
Flat in Shadyside
4.91 out of 5 average rating, 116 reviews

Betwn Walnut & Ellsworth! Sleeps4! Parking&Laundry

LOCATION! LOCATION! This apartment is approx 200 feet to Ellsworth Avenue and approx 700 feet to Walnut Street! My apartment features a deck, open-concept layout, central air, and free laundry. One parking spot is available for free, if reserved in advance. Please see the parking policy below. The apartment sleeps 4 people. The bedroom has a queen bed. The living room has a sofa that conveniently folds down into a queen-sized bed.

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 £23 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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