Holiday rentals in Cheswick

Mayberry Escape

Discover the charm of this inviting 3-bed, 3.5-bath Monroeville home! Immerse yourself in luxury with a heated pool (seasonal), rejuvenating infrared sauna, expansive decks, a private backyard, a fully equipped kitchen, a finished basement, and a delightful fire pit overlooking the pool. Experience comfort and style with off-street parking included. Enquire now to make this your own sanctuary! ***If you enjoy this space, the owners are amenable to selling. Please contact for more information***

2BR Apt. /Pittsburgh/East/Regent Square/Frick Park

First floor 2-bedroom apartment with classic decor. Modern bath/kitchen with complete utensils. Wi-Fi & wired gigabit network. Two TVs with service. Appropriate for business traveler, families with older children. Living and dining room accommodates 8-10 people. Convenient to downtown, Oakland/universities. Across street parking. Nearby restaurant/stores and park in walking distance. Open bar. No per-person or amenities charges. Virtual tour at https://my.matterport.com/show/?m=BFeAkSV4ekM

Allegheny River Aqua Villa

Experience a unique getaway on the Allegheny River with our exceptional tiny home built on a barge! This floating haven offers a distinctive reverse floor plan with luxury & breath-taking views! Lower Level- Two inviting bedrooms, each with twin beds that can convert into a king for your comfort - Full bathroom with Dual Rainfall Shower Heads. Upper Level - Open Concept Living with TV & Internet, Fully Equipped Kitchen & Peninsula. See-through gas fireplace! Patio Doors & Wrap around Decks!

Cabin in Pittsburgh. 20 minutes to Pittsburgh

Please do not request booking until you have contacted the owner for pricing. The cabin is a perfect place to stay while visiting friends and family in Pittsburgh. Private and comfortable, clean and convenient to many locations in Pittsburgh. Only 20minutes to the city, and stadiums. The cost you see per night is for 2 guests. Added adults (18 and over) are $25.00/adult/day. Children under 18 are $10.00/child/day. Children under 2 are free. Dogs are $10.00/day. I will collect that later.

Cozy King Suite with Parking!

In the heart of Shadyside! 1 Block to Walnut St w/ FREE OFF STREET PARKING Short Walk to UPMC & West Penn hospitals, 3 min drive to CMU & Pitt! 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!

Oakmont Area - Carriage House

Carriage House apartment in East Oakmont is minutes away from Oakmont Country Club and is also close to Longwood at Oakmont and Presbyterian SeniorCare. Two parking spaces provided. Owners live on-site, but are very hands-off unless you need us! TONS of restaurants, shops, and breweries within minutes. The town of Oakmont is one mile away and the infamous Oakmont Bakery is just down the hill. Easily accessed from the PA Turnpike and from Route 28. 11 miles from downtown Pittsburgh.

The Pitt Stop

Relax and enjoy in this comfortable peaceful place. It is situated in a convenient location close to the City of Pittsburgh, approximately 20 minutes from downtown and the statiums as well as many city attractions such as the Pittsburgh Zoo! If you are in town for other reasons we have great restraunts, bars and brewerys and the famous oakmont bakery all within 5-7 minutes away. We have added 2 complementary guest passes to Anytime Fitness only a 5 minute drive from the Pitt stop.

Cozy, Modern Loft Style Apartment!

A spacious loft with a king size bed that will make you feel like you are in a luxurious hotel room. This unit is brand new in 2024 from floors to ceiling! full kitchen with stainless appliances and a ton of counter space. It is fully equipped with dishes, silverware, baking utensils, bowls and more! Beautiful brand new bathroom with tall ceilings and ready for your stay with fresh towels, shampoo and body wash. 65" Swivel TV! Located just minutes from Route 28 for easy city access.

Quiet Cottage House Near Pittsburgh

Welcome to your Pittsburgh winter home! This warm, inviting space sleeps up to four guests and is perfect for families visiting for events or friends gathering for a winter escape. Whether you’re in town to see relatives, cheer on the Steelers or Penguins, or simply enjoy a cozy seasonal getaway, our home is ready. Nestled in a quiet, friendly neighborhood just minutes from the heart of Pittsburgh, this home offers the comfort of a tranquil retreat with easy access to Pittsburgh.

Comfort Central

Comfort Central is in a very safe neighborhood with on street parking. It's 7 miles from downtown Pittsburgh, universities, stadiums, museums and 2 miles from RIDC Park in O'Hara Township. It' conveniently located within an 8 minute drive from the Pennsylvania Turnpike . There is a hospital and park nearby. The Waterworks Mall which includes grocery stores, retail shopping, restaurants, wine and spirits store, fast food , and movie theater is a short 5 minute drive.

Upstairs Flat in a Historic Craftsman Big Bungalow

Experience a comfortable stay in our charming bungalow, nestled on a peaceful corner lot less than a mile from Oakmont Country Club and about 20 minutes from downtown Pittsburgh. Whether you’re a golf enthusiast or simply exploring the area, this is the perfect home base. The private second-story apartment offers its own entrance and overlooks a beautiful backyard—ideal for solo travelers or small families alike. Free street parking. Please observe street sweeping hours.

2br gem in cute small town.

The whole group will enjoy easy access to everything from this centrally located place. Grab a book about Pittsburgh from the coffee table and find some fun things to do or have game night with the selection of board games. Sip a beverage on the back porch or make s’mores at the fire pit. Easy access to Pittsburgh, hop on 28 and be there in no time, or ride one of the busses that stop outside the door. 13 miles to PNC Park 14 miles to Acrisure Stadium