Holiday houses in Cheswick

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Top-rated holiday rentals in Cheswick

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Superhost
A two-story white house features distinct green shutters and a welcoming front porch. The entrance is framed by steps leading to the doorway, surrounded by well-manicured landscaping. A detached garage is visible in the background, with a clear blue sky providing a bright backdrop.
Home in Harwick
4.79 out of 5 average rating, 19 reviews

Quiet 3 BR Suburban Home Close to Pittsburgh

If you are looking for a quiet community close to everything, this is your destination! Only minutes from the PA turnpike, seconds to Route 28 and a brief 20 minute drive to downtown Pittsburgh! 3 BR's (Two queens and one full), big back yard, full kitchen amenities, dining room, comfortable living area and more! This house is ideal for a professional or out of town visitor that needs to be close to the major highways around the greater Pittsburgh area while enjoying a "at home" experience!

Top Guest favourite
The floating home is presented from an aerial view, showcasing its unique two-level structure nestled on the calm waters of the Allegheny River. The wrap-around deck and patio doors are visible, enhancing the connection to nature, with lush greenery lining the riverbank.
Houseboat in Blawnox
4.99 out of 5 average rating, 95 reviews

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!

Top Guest favourite
Apartment in Oakmont
5 out of 5 average rating, 49 reviews

Upstairs Flat in a Historic Craftsman Big Bungalow

Experience a comfortable stay in our charming bungalow on a peaceful corner lot along historic, tree-lined California Avenue in Oakmont, 20 minutes from downtown Pittsburgh. The private second-story apartment has its own entrance and overlooks a beautiful backyard, making it an ideal home base whether you're visiting family, exploring the area, attending an event, or simply relaxing. Ample free street parking is available right outside the entrance. Please observe posted street-sweeping hours.

Guest favourite
The cabin exterior is seen surrounded by lush greenery. A small outdoor dining area features a table and four chairs under a yellow umbrella. A portion of the cabin façade is visible with wooden logs, while a stone fire pit can be seen in the foreground.
Cabin in Pittsburgh
4.9 out of 5 average rating, 178 reviews

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.

Guest favourite
A single-story brick house is situated on a gently sloping lawn, surrounded by greenery. The entrance features a welcoming porch with steps leading up. A small garage is visible on the left side, and the driveway is paved, adding accessibility to the property.
Home in New Kensington
4.9 out of 5 average rating, 49 reviews

Cozy Rural Country Retreat Close to Pittsburgh

This House offers Very Relaxing to Nature with Big yard provide good Privacy with small rolling hills little further away from City. Home features 2 Bedroom 2 Bath with Plenty of space for outdoor and Indoor activities such as 2 big Screen TV, Free Wi-Fi, Sunroom, Celing fans, Office Space and Comfortable Mattress and Sofa. Updated Kitchen with Appliances with Laundry and Dryer .Bathroom provides with lines, shampoo, lotion and hair dryer etc. Outdoor Grill for cookout and catching fresh air.

Top Guest favourite
A spacious bedroom features a wooden bed with crisp white bedding and a decorative yellow accent pillow. A bedside lamp illuminates a dark wood nightstand. A tufted bench sits at the foot of the bed, and light streams in through a nearby doorway.
Apartment in Aspinwall
4.99 out of 5 average rating, 106 reviews

Aspinwall 1 bedroom Apartment

Newly updated 1 bedroom 1 bathroom apartment in the heart of the charming town of Aspinwall. Private exterior entrance with porch and patio, new kitchen, refinished original hardwood flooring, updated bathroom, living/dining room with decorative fireplace and 50” smart TV, spacious bedroom with queen, large closets and pocket doors all warmly decorated. 2 blocks from primary business streets for dining and shopping, under 10 minute walk to both UPMC St Margaret hospital and riverfront park!

Top Guest favourite
Townhouse in Mt. Lebanon
4.99 out of 5 average rating, 174 reviews

Private Mt Lebanon Retreat Near Airport/Downtown

Welcome to your home away from home! This recently remodeled townhouse offers the perfect blend of comfort and style, situated just 20 minutes from the air port and city’s major stadiums. Ideal for all travelers, our home is nestled in a peaceful suburb with easy access to public transportation, nearby parks, and charming small businesses and shops. • Two bedrooms featuring king-sized beds. • An expansive kitchen, complete with peninsula and breakfast bar. We look forward to hosting you!

Top Guest favourite
Apartment in Verona
4.94 out of 5 average rating, 64 reviews

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.

Top Guest favourite
Home in Verona
4.96 out of 5 average rating, 55 reviews

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.

Guest favourite
The exterior of a three-story house is shown, featuring dark siding and a peaked roof. A welcoming front entrance is accessed via a steps leading to the door. Lush green shrubs frame the house, contrasting with the bright grassy area in front.
Apartment in Pittsburgh
4.91 out of 5 average rating, 544 reviews

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.

Top Guest favourite
Home in New Kensington
4.96 out of 5 average rating, 23 reviews

Newly Furnished Clean & Cozy

This listing is newly furnished, freshly painted and a cozy home. Whether your visiting for work, family time or a weekend getaway, our home offers the perfect balance of space, comfort & convenience. We offer 2 bedrooms, full bath, private laundry, fully equipped kitchen, electric fireplace & private parking . We are around 25 miles to downtown Pittsburgh. (30 minutes) Lots of restaurants to choose from in Oakmont & New Kensington. Coffee bar waiting on yinz!

Superhost
A cozy living area features two comfortable sofas, one adorned with blue cushions and a throw blanket. A dark coffee table is centered on a textured rug, surrounded by natural light from large windows dressed with gray curtains. A flat-screen TV is mounted on the wall.
Apartment in Springdale
4.85 out of 5 average rating, 115 reviews

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

Popular amenities for Cheswick holiday rentals