Vacation rentals in Shadyside, Pittsburgh

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Top-rated vacation rentals in Shadyside, Pittsburgh

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Guest favorite

Apartment in East Liberty

4.96 out of 5 average rating, 123 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.

Feb 23 – Mar 2

G$19,834 GYD per night

Guest favorite

Guest suite in Highland Park

4.97 out of 5 average rating, 139 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.

Oct 10 – 15

G$18,005 GYD per night

Guest favorite

Apartment in Shadyside

4.83 out of 5 average rating, 109 reviews

Shadyside: Ultra Lux, 1 Bed/1 bath

Shadyside gem! Chic, stylish , spacious. Conveniently situated in the heart Pittsburgh's favorite neighborhood. Exceptionally comfortable layout includes an in-suite laundry & exclusive front porch! Eat-in or dine out at one of the many near-by restaurants. Fabulously located to quaint shops, unique restaurants, beautiful city parks, culture-rich museums, state-of-the-art sports facilities, Universities, Hospitals. Wonderful walkable location. Easy access to public transportation too!

Jan 20 – 27

G$35,561 GYD per night

Guest favorite

Home in Squirrel Hill South

4.93 out of 5 average rating, 263 reviews

Upscale Modern 2 BR Apartment

This spacious, newly renovated, fully equipped and private access apartment was built for your enjoyment! The granite counter tops and porcelain tiled shower are a hint of the luxuries throughout. You can park on the property or on the street. Located in the heart of Squirrel Hill, right near Schenley park, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Waterfront, Downtown, Museums & Galleries, Universities, hospitals, and all Sports venues.

Sep 16 – 23

G$27,041 GYD per night

Guest favorite

Apartment in Shadyside

4.95 out of 5 average rating, 220 reviews

Bohemian Place Shadyside Style

Designed for longer stays. Sanitized for each guest, 2 bdm apt with private entrance to the 3rd floor apartment. Steps from shops, grocery, restaurants, public transportation. *Private ent., extra twin foam bed. *Kit incl, plates, toaster oven, microwave, stove, H2O kettle, French Press * 1 block RESTAURANTS Walnut St./ Ellsworth Ave / Museums *HV/AC *5 min. walk grocery. *UPMC Shadyside, Pitt, CMU, Chatham Univ. Bike rent - 1/2 blk. bike route *2 min. walk to busway to downtown.

Feb 10 – 17

G$19,571 GYD per night

Guest favorite

Apartment in Point Breeze

4.95 out of 5 average rating, 387 reviews

Charming cozy apartment with deck.

This little jewel of an apartment is charming and cozy, with private entrance, 1 bedroom, small sitting area, fully-equipped kitchen, bath, laundry access, wifi and private deck. We are on a quiet shady street near 644-acre park. 2.5 miles to universities, 1 mile to Bakery Square. NO CLEANING FEE, so a better value than other listings! Comfortable queen-sized bed with memory foam mattress topper. Many nice amenities and original artwork. Small but homey with lots of little luxuries!

Jan 7 – 14

G$17,231 GYD per night

Guest favorite

Apartment in Shadyside

4.89 out of 5 average rating, 102 reviews

Victorian home 2 bedroom Shadyside

Bright, sunny, spacious 2 bedroom apartment with 1 parking space in the heart of Shadyside. This apartment is in a Victorian home on a quiet street. There is a train that runs below the street I feel it is part of the history and charm of city living. Shopping, restaurants, UPMC hospitals, Universities, museums and cultural activities, within walking distance or public transportation. The unit has been recently updated, beautiful new bathroom and hardwood flooring through out.

Sep 2 – 9

G$29,824 GYD per night

Guest favorite

Apartment in Bloomfield

4.91 out of 5 average rating, 359 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).

Oct 4 – 11

G$22,747 GYD per night

Superhost

Apartment in Shadyside

4.85 out of 5 average rating, 212 reviews

🔥Pristine King Bed Suite ⚡️ Hidden Gem 💎 PITT / CMU ✨ Pet Friendly 🐶

Pristine 1 bedroom apartment in the heart of Shadyside! Prime location, short walk to plenty of restaurants, shops, coffee shops & UPMC Shadyside hospital! Fully equipped for both long and short stays. 🔹King bed (memory foam mattress) 🔸Pet friendly! 🐶 🔹Fully stocked & equipped kitchen 🔸Smart Home Technologies 🔹Central AC/ Heat 🔸Luxurious waterfall shower head🚿 🔹Free street parking 🔥Message today to secure your reservation!🔥

Jan 17 – 24

G$20,698 GYD per night

Guest favorite

Guest suite in Bloomfield

4.98 out of 5 average rating, 178 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.

Oct 29 – Nov 5

G$20,844 GYD per night

Superhost

Tiny home in Bloomfield

4.89 out of 5 average rating, 170 reviews

Not so tiny house with full kitchen & patio swing

Tiny house with lots of windows and natural light, conveniently located in one of Pittsburgh's most up and coming neighborhoods of Garfield and convenient to surrounding neighborhoods of East Liberty, Bloomfield, Shadyside, Oakland, Highland Park, Lawrenceville, and the Strip District. Relax and enjoy a book on the front patio, get your work done on the foldout desk, or fold up the murphy bed and enjoy your yoga practice.

Feb 11 – 18

G$25,985 GYD per night

Guest favorite

Apartment in Bloomfield

4.91 out of 5 average rating, 232 reviews

Cozy Entire AptA Friendship Park & free parking

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.

Aug 9 – 16

G$29,894 GYD per night