Vacation rentals in Squirrel Hill

4.91 out of 5 average rating, 104 reviews

Huge Open Concept 2BR by Walnut

HUGE apartment In the heart of Shadyside w/ room for the whole family! 1 Block to Walnut St & FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 2 floor apt in a prime location, w/ all Shadyside has to offer just steps away! Enjoy dozens of restaurants, shops, coffee shops, & fitness studios close by. The building was gutted & remodeled in March 2024, everything down to the soundproofing, granite kitchen, and top of the line appliances is brand new!

5 out of 5 average rating, 61 reviews

Thoughtful, Furnished, Convenient in Squirrel Hill

Thoughtful Renovation/Restoration in a 1920's Duplex; Fully furnished and Meticulously Appointed. Located in Squirrel Hill with great access to Squirrel Hill Business District, Shadyside, East Liberty, Oakland, Schenley Park and Frick Park and Downtown During your stay in Pittsburgh, live in a furnished, residential property in the neighborhood of Squirrel Hill. The property is a completely renovated 2 bedroom, 2 bathroom apartment in a duplex with flexible layout and room for a home office.

4.81 out of 5 average rating, 118 reviews

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.

4.9 out of 5 average rating, 239 reviews

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)

5 out of 5 average rating, 70 reviews

Lavish Squirrel Hill - 3rd Floor

Nestled 2 blocks off of the Squirrel Hill business district this 3rd floor paradise has 3 bedrooms, full kitchen (walnut cabinets and granite counters), timeless black and white bathroom with cast iron tub. This oasis is "THE" place to stay while visiting Pittsburgh. Close to the Universities, and walking distance to 2 of Pittsburgh's parks (Frick and Schenley), you can literally catch a bus into town right outside the door (While still being an extremely quiet street with ample parking).

4.93 out of 5 average rating, 317 reviews

Home in Pittsburgh

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.

4.95 out of 5 average rating, 20 reviews

Chez Morgan Suite One (Greenfield)

Simply safe, clean, central location, natural light, comfy bed, personal privacy. Non Smoking 1 BR apt. 1 block 58 Greenfield bus. Uber/Lyft avail. 2.5 mi.-CMU, 2.7 mi.-Pitt. Close to Duquesne, Carlow. (Hospitals) Presby, Montefiore, Magee-Womens, Shadyside, Mercy, South Side; Downtown, Waterfront. Good for couples, grad student, researcher, business traveler. CMU bus 2 blocks, free with CMU ID. Window AC June 1-Oct 1. As I have allergies, we cannot host service/emotional animals.

4.98 out of 5 average rating, 102 reviews

"April's Retreat" Regent Square King Bed Frick Prk

Take it easy at this tranquil getaway that is close to everything Pittsburgh. You'll enjoy the one bedroom apartment on the 2nd floor of this historic building in Regent Square. Walk to Frick Park, restaurants, coffee shops and bars on Braddock. Hike or mountain bike on the 22 miles of trails. Small and well-appointed kitchen if you like to prepare your own meals. Tons of natural light. Close to bus routes. Need more space? Traveling with others? Check out my other 2bd listing.

4.94 out of 5 average rating, 134 reviews

Walk to CMU, Pitt, Walnut! Parking! King Suite!

This BRAND NEW apartment is in an ideal location in Shadyside close to CMU, Pitt, Walnut Street and much more! My apartment features a deck, open-concept layout, bedroom with a walk-in closet, central air, and free laundry. One parking spot is available IF IT IS RESERVED IN ADVANCE. The apartment sleeps 4 people. The bedroom has a king-sized mattress. The living room has a sofa that very conveniently folds down to transform into a queen-sized bed. There is a spacious deck.

5 out of 5 average rating, 80 reviews

Home in Pittsburgh

Cheerful 3-bedroom home with on-street parking

Enjoy your stay in this beautifully renovated 3 story 1920s centrally-located home in the Greenfield neighborhood of Pittsburgh (right next to Squirrel Hill). Less than 10 minutes to Downtown, PPG Arena, Bakery Square, CMU, Pitt, Chatham, and Duquesne University. Minutes away from excellent restaurants and bars in Pittsburgh. Fully equipped entire home for an extended or few nights stay. Enjoy outdoor seating on the front porch and back deck with a fenced in backyard.

4.88 out of 5 average rating, 501 reviews

Home in Pittsburgh

PRIVATE MINI STUDIO (D2)

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).

Guest suite in Pittsburgh

4.91 out of 5 average rating, 228 reviews

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.

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Other great vacation rentals in Squirrel Hill

5 out of 5 average rating, 8 reviews

Shadyside/Pittsburgh @G Modern & Cozy Private BD

AdityaRating, 5 stars1 week ago

Great stay! Would definitely return

4.69 out of 5 average rating, 45 reviews

Exquisite Super Cozy Smart Home 3 (Alexa control)

NisarujRating, 5 stars10 months ago

The bedroom and bathroom were clean. Easy to check-in and the host responded very quickly and helped me resolve issues. Recommended.

5 out of 5 average rating, 37 reviews

Oakland/Pittsburgh @A Modern & Stylish Private Bdr

TeresaRating, 5 stars1 week ago

The room is spacious with wood bed and nice furnitures, which you won't expect in most airbnb. The bedding and towels are cotton. the mattress are memory foam on top, Which is probably the most comfy airbnb bed I have ever had. Walkable distance to Universities. Nice park is just 5mins away.

Superhost

5 out of 5 average rating, 4 reviews

Private Suite | Student & Medical Professionals R8

SeydaRating, 5 stars1 month ago

It was a pleasure staying at this place. The location was great, the space was clean, and hosts were responsive and helpful. Highly recommend!

4.9 out of 5 average rating, 444 reviews

PRIVATE FULL STUDIO IN PITTSBURGH (C2)

DaveRating, 5 stars3 weeks ago

I stayed in Natallia's apartment for 4 nights during a recent trip to Pittsburgh. Located in a nice quiet neighborhood (Friendship) with a Whole Foods and Primanti Brothers restaurant a very short walk away. Check in was very easy with an electronic code for both the main door and apartment door. The apartment is small, basically a nice hotel room with a kitchen, which matched my expectations. I was able to work remotely, cook meals, and log into streaming services on the TV. The bed was very comfortable as well. In the bathroom, complimentary soaps and body wash were provided. I would recommend Natallia's apartment to anyone staying in Pittsburgh for business or pleasure.

4.71 out of 5 average rating, 129 reviews

Secluded Room in Squirrel Hill

JudeRating, 5 stars2 weeks ago

The location was wonderful, the unit was comfortable and clean, and Sean is a fantastic host. Would absolutely recommend!

4.88 out of 5 average rating, 169 reviews

Cozy 2BR steps from Walnut St!

ScottRating, 5 stars1 day ago

Jake was a responsive host. We had a few questions and needs during our stay. Jake responded with minutes and was respectful and helpful. The apartment was clean and had all we needed. The neighborhood is quiet, always found parking, and conveniently located near shops and restaurants. Quick trip downtown and to the pro sports venues. Highly recommend.