Holiday houses in Shadyside, Pittsburgh

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Top-rated holiday rentals in Shadyside, Pittsburgh

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Guest favourite

Apartment in East Liberty

4.96 out of 5 average rating, 125 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

Guest suite in Highland Park

4.97 out of 5 average rating, 143 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.

Guest favourite

Apartment in Shadyside

4.84 out of 5 average rating, 111 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!

Guest favourite

Home in Squirrel Hill South

4.92 out of 5 average rating, 265 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.

Guest favourite

Apartment in Shadyside

4.95 out of 5 average rating, 223 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.

Guest favourite

Apartment in Point Breeze

4.95 out of 5 average rating, 394 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!

Guest favourite

Apartment in Shadyside

4.89 out of 5 average rating, 104 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.

Superhost

Apartment in Shadyside

5.0 out of 5 average rating, 4 reviews

#7 – Cozy studio in the heart of Shadyside

This cozy, fully furnished studio apartment is located in the heart of Shadyside, five short blocks from Walnut Street, the most iconic street in Pittsburgh known as a shopping and dining destination. The apartment is also close proximity to CMU and PITT, making it an ideal place to stay for students, visiting professors and researchers. Carnegie Mellon's free shuttles stop right in front of the building, and you can even walk to CMU and PITT campus.

Guest favourite

Apartment in Bloomfield

4.9 out of 5 average rating, 362 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

Guest suite in Bloomfield

4.98 out of 5 average rating, 181 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

Apartment in Bloomfield

4.91 out of 5 average rating, 235 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.

Guest favourite

Guest suite in Bloomfield

4.98 out of 5 average rating, 233 reviews

Large victorian 3rd flr apt in walkable eastend

An entire third floor apartment of a historic Colonial Revival house. Two bedrooms, each with a firm queen memory foam bed, one bathroom with claw foot tub/shower, huge living room with seating area and desk, and a fully equipped kitchen with washer and dryer. Walk up to third floor. A queen air mattress bed or pack n' play can be added to any one of the bedrooms or the living room, just let us know.