
Holiday rentals in Squirrel Hill
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Squirrel Hill
Guests agree: these stays are highly rated for location, cleanliness and more.

Minimalist Townhouse with Stunning Skyline View
This townhouse is a gem in Pittsburgh! Located on a quiet street in Greenfield, it is central to everything the city has to offer. Situated on top of a hill, the skyline can be seen from the deck, and it’s breathtaking with a sunset! Walkable to Squirrel hill, less than 10 minutes driving from downtown, Shadyside, Oakland. The cohost has lived in Pittsburgh for 6 years and would be delighted to offer recommendations around the city. Meticulous cleaning standards are followed for your safety.

Darling basement one-bedroom
This simple basement suite is safe and convenient. Located on a quiet street with walking to restaurants, library, and movie theater with easy bus access to Pitt, CMU. Equidistant to Frick and Schenley Parks with hiking and biking trails, tennis, soccer, playground. Private entrance, off steep-ish driveway . Free street parking. Lower ceiling. No pets, smoking outside only. I have my children every other weekend; they have quiet hours 9pm-8am. Please inquire for dates if that might annoy.

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)

Lovely, cozy Beacon guest suite in Squirrel Hill
This lovely and cozy one-bedroom guest suite is located in a safe and convenient neighborhood in the heart of squirrel hill. The suite features a open living and work space with lots of natural light and a gorgeous view of the beautiful Beacon street. You can enjoy some quality reading time or get some work done in our reading and working corners. Our high quality bedding ensures you have a nice rest after a busy day. It is only minutes from nearby restaurants. Very close to Pitt and CMU.

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.

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.

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).

Renovated large private studio in Squirrel Hill
Cozy and lovely large studio with garden, separate private entrance, kitchen, and full bathroom. Located in the central and convenient neighborhood of Squirrel Hill, close to CMU, University of Pittsburgh and Chatham University, right next to Schenley Park and walking distance (only 2 blocks) to all the cafes, restaurants, shops, movie theater and local amenities of our amazing neighborhood. Downtown Pittsburgh is only 10-12 minutes drive.

Cozy Entire Apt 3 *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 and eclectic flair. This 3rd floor space has 1 bedroom with a queen bed, a well equipped kitchen, and a luxurious bathroom & shower.

Spacious New Apartment
Welcome to Pittsburgh! Our garden-level Airbnb is bright, spacious, and ideally located in Squirrel Hill in proximity to universities, hospitals, Schenley Park, public transportation, and major highways. (Pigeon bakery, a popular breakfast place, is at the corner!) Whether you are here for work, family, or vacation, our Airbnb will enable you to have a comfortable and convenient stay.

Squirrel Hill Chic • Spacious 1BR + Parking & Gym
Experience modern comfort in this fully renovated spacious 1BR located in the heart of Squirrel Hill. Minutes to CMU, Pitt, UPMC hospitals, Shadyside, shops, cafés, and Schenley Park. Enjoy a stylish open layout, premium finishes, a full kitchen, private parking, laundry, and a gym in the building. Safe, walkable, and ideal for students, professionals, and long-term stays!

Cozy Apt in Heart of Shadyside - Private Balcony
Brand new listing in the heart of Shadyside! 1 Block to Walnut St, short walk to UPMC & West Penn hospitals, close to CMU & Pitt! 2BR/1 bath apartment with private balcony in a PRIME LOCATION just off Walnut Street, enjoy dozens of restaurants, shops, coffee shops, and fitness studios close by! Fully stocked for both long and short term stays!
Popular amenities for Squirrel Hill holiday rentals
Other great holiday rentals in Squirrel Hill

Cozy King Suite Just off Walnut

Mexican War Streets, The Heinz Suite.

* Carson Room - by UPMC, Pitt, CMU

Upscale 2BR suite ~ Free Parking & Walkable!

Cozy 2BR steps from Walnut St!

The Maverick by Kasa | Steps to Bakery Square

Cozy King Bed Suite ~ Free Parking & Ground Floor!

Cozy King suite! $0 cleaning fee
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Rappahannock River Holiday rentals
- Niagara Falls Holiday rentals
- Rentals with a washing machine and dryer Squirrel Hill
- Family-friendly rentals Squirrel Hill
- Flat rentals Squirrel Hill
- Townhouse rentals Squirrel Hill
- Fitness-friendly rentals Squirrel Hill
- Rentals with a fireplace Squirrel Hill
- Rentals with breakfast Squirrel Hill
- House rentals Squirrel Hill
- Rentals with a firepit Squirrel Hill
- Rentals with a patio Squirrel Hill
- Pet-friendly rentals Squirrel Hill
- Rentals with outdoor seating Squirrel Hill
- PNC Park
- Carnegie Mellon University
- Seven Springs Mountain Resort
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Acrisure Stadium
- Idlewild & SoakZone
- University Of Pittsburgh
- Point State Park
- Kennywood
- Raccoon Creek State Park
- National Aviary
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- David Lawrence Convention Center
- Schenley Park
- Carnegie Museum of Art
- Children's Museum of Pittsburgh
- Randyland
- Senator John Heinz History Center
- Cathedral of Learning
- Stage AE
- Petersen Events Center
- Carnegie Science Center




