Vacation rentals in Squirrel Hill

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Top-rated vacation rentals in Squirrel Hill

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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.

Nov 5 – 12

G$20,837 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 7 – 14

G$16,532 GYD per night

Superhost

Apartment in Shadyside

4.85 out of 5 average rating, 236 reviews

Shadyside: Perfect, Chic, Stylish w. free parking!

So beautiful! Modern, vibrant, well appointed! Perfectly located in Shadyside: Pittsburgh's most desirable neighborhood! Famous, historic Walnut Street is just around the corner. Charming district w. many shops, restaurants, fitness studios. Steps from parks, museums, sporting facilities, & public transportation (why drive?). It's the perfect location for visiting CMU, University of Pittsburgh, Chatham, Duquesne University, or Carlow. On-site car parking. (Sorry, no trucks or SUV's)

Jul 9 – 16

G$29,566 GYD per night

Superhost

Guest suite in Squirrel Hill South

4.83 out of 5 average rating, 155 reviews

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.

Sep 4 – 11

G$30,341 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$27,028 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.

Aug 27 – Sep 3

G$19,435 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!

Feb 3 – 10

G$17,223 GYD per night

Superhost

Apartment in Greenfield

5.0 out of 5 average rating, 9 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.

Jun 26 – Jul 3

G$18,223 GYD per night

Guest favorite

Home in South Side Flats

4.91 out of 5 average rating, 348 reviews

Urban converted gas station in heart of South Side

My place is close to art and culture, restaurants and dining, and family-friendly activities. The southside is loaded with bars and restaurants, grocery and clothing stores, galleries, public library and pool. It is very near downtown Pgh and has great bike/running trails along the river. You’ll love my place because of the outdoors space, the neighborhood, the light, the comfy bed, and the kitchen. My place is good for couples, business travelers, and furry friends (pets).

Jun 19 – 26

G$25,762 GYD per night

Superhost

Home in Squirrel Hill South

4.82 out of 5 average rating, 128 reviews

New remodeled Modern 2BR suite for 4

This newly renovated, state of the art, private apartment is sure to make your stay in Pittsburgh enjoyable. Modern yet comfortable this apartment boasts granite countertops and a luxuriously tiled bathroom with a washer and dryer for your every day needs. Located in the heart of Squirrel Hill, right near Schenley park, PITT, CMU, the Squirrel Hill business district and bus lines. Easy Access to Bakery Square, Shadyside, Downtown, Museums & Galleries, and all Sports venues.

Apr 19 – 26

G$24,251 GYD per night

Guest favorite

Guest suite in Squirrel Hill South

4.91 out of 5 average rating, 200 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.

May 13 – 20

G$27,189 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 28 – Feb 4

G$21,761 GYD per night