Holiday houses in Squirrel Hill

Immaculate Double King Suite| 2 Decks| A+ Location

Enjoy our immaculate 3 BR suite on S Highland Ave, right in the heart of Shadyside. This is a brand new construction building in 2025 with a modern design, ultra-comfortable beds, and two private decks. This apartment is just steps away from several local shops, cafes, and dining options in one of Pittsburgh’s most vibrant neighborhoods. ⭐1 King Bed / 2 Queen beds (memory foam mattresses) ⭐Twin Rollaway bed + Pack N Play ⭐Free in-unit washer/dryer ⭐2 Desks with speedy WiFi ⭐24/7 guest support

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.

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.

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!

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).

Huge King Suite Just off Walnut

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

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 Home - Walk to Walnut St - Free Parking

Beautifully maintained Shadyside row home one block from Walnut Street - and no cleaning fee. Bright, open living spaces, updated appliances, lots of natural light, yet quiet inside. Walk to boutiques, cafes, and restaurants; minutes to CMU, Pitt, and UPMC - ideal for campus visits, hospital stays, or weekend trips. Two off-street parking spots, a covered front porch, and a private deck. Finished basement adds a 90" TV plus flexible space for an office, playroom, or cozy movie room.

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.

Lovely, cozy Beacon guest suite in Squirrel Hill

This lovely and cozy studio-style guest suite is located in a safe and convenient neighborhood in the heart of Squirrel Hill. The space features an open living and working area filled with tons of natural light. You can enjoy a quiet reading corner or a comfortable workspace for study and remote work. Our high-quality bedding ensures a restful stay after a busy day. The suite is just minutes from a variety of restaurants and is very close to both the UPITT and CMU.

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.

New & Cozy Apt in Squirrel Hill

Welcome to our newly renovated walk-out basement unit in Squirrel Hill, one of the safest neighborhoods of Pittsburgh. It is central to all of the best attractions. Pittsburgh downtown is only 15 minutes drive. The unit enjoys proximity to Frick Park, Schenley Park, Carnegie Mellon University, University of Pittsburgh, grocery stores, cafes, restaurants, shops, movie theater, and local amenities on Murray, Forbes, and Shady avenues.