
Vacation rentals in Cheswick
Find and book unique accommodations on Airbnb
Top-rated vacation rentals in Cheswick
Guests agree: these stays are highly rated for location, cleanliness, and more.

Ranch Home: Cozy & Modern!
Kick back and relax in this modern ranch style home! Enjoy a soothing bath with the warmth & ambiance of the fireplace. There is a back porch that has seating coupled with a fire pit. You could park 2-3 vehicles in the driveway. There is also plenty of parking available on the street. LOCATION: You are roughly 2.8 miles from Oakmont, which offers many entertainment options! Oakmont Country Club is only 3.9 miles away. The home is 12.8 mi from downtown Pittsburgh, where the stadiums are!

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.

Wyckoff-Mason Log House 1774 Historic Landmark
Stay in the historic Wyckoff-Mason House, a Pittsburgh Historical landmark. This beautifully kept log house built in 1774-75, still maintains the colonial charm of pre-revolutionary times. This property has a storied past, including local lore that it was the residence of William Penn’s brother and was visited by Benjamin Franklin. This relaxing getaway is located in one of Pittsburgh’s eastern suburbs. Get the best of the countries antiquity while visiting the city. We love all people.

Gorgeous Modernized Cabin + Hot Tub + Pool Table
Welcome to this incredible, fully renovated true log home with a massive entertainment room consisting of a pool table, ping pong table and more 🔥 3 full sized bedrooms along with an additional room with a pull out couch. There are 3 private bedrooms or use it as 4 with a wall separation. Fully equipped kitchen with quartz countertops and stainless appliances. Large front porch with plenty of furnishings and a rear deck with a view of a farm. Huge 2 car garage for parking and a driveway! 🚘

Pet friendly/safe by Oakmont, Veltres + Pittsburgh
Relax with the whole family at this cozy pet-friendly home away from home that hosts 6 guests + pets. You will be renting a single-family raised ranch home, featuring 3 bdrms, 1 full bath, living rm, dining rm, fully stocked kitchen, sunroom & outdoor deck & yard. Just 4.3 mi to Oakmont center, 1 mi to Veltre's Wedding Centre, 3 miles to Oakmont Country Club, and 12 mi to Pittsburgh. Also close to breweries, wineries, shops @ Fox Chapel, Harmar, St. Margaret's and AHN Harmar hospitals.

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.

Cute Apt Minutes from Downtown and Stadiums!
🏡 Welcome to this charming home just minutes from downtown Pittsburgh & the stadiums! Perfect for couples, friends, or solo travelers. Enjoy a spacious fenced backyard, comfy living areas, and easy access to city highlights. No parties, but great vibes always. 🛋️ Inside, you’ll find a charming, thoughtfully decorated home that’s as functional as it is cute. 🌿 Out back, you’ll love the spacious fenced-in yard — perfect for sipping coffee, or unwinding after a day in the city.

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.

Elegant Escape Near Pittsburgh Pa - 13mi
Forget your worries in this modern, spacious and serene space. Guests have access to the entire home located in the quaint town of Verona, Pa. Relax and enjoy the FULLY remodeled home otherwise you will be in close proximity to several restaurants, bars & shops making it easy for a night out. A brisk 20 minute drive will land you Downtown Pittsburgh! Whether you are traveling for business or leisure this Elegant Escape will easily be your home away from home.

Pittsburgh Area 2 Bedroom Apt.
Comfortable, Convenient & Clean 2 bedroom apartment (1 queen bed & 1 twin size day bed). Located on a "Pittsburgh Hill" you'll remember in Forest Hills a quiet residential eastern suburb of city. Free off street parking. Downtown & Stadiums 10 mi. Universities, Medical Center & Carnegie Museums 8 mi. Monroeville Convention Center & Sri Venkateswara Temple 5mi, International A/P 27 mi. PENS Hockey Arena 9 mi. I-76 PA turnpike 8 mi. Kennywood Park 5 mi.

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 vacation rentals
Other great vacation rentals in Cheswick

Spacious 6BR Home, No Stairs, Lots of Parking

Basement apartment with private entrance and bath

Cottage on a hill

Tiny House on a Homestead

The Fawn Room - Double Bed

Cozy Private Room

Cozy warm lovely Squirrel Hill free park & wifi

Phenom cozy ROOM ctrl to DT, UPMC, Oakland, Bkr Sq
Destinations to explore
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Washington Vacation rentals
- Mississauga Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Pocono Mountains Vacation rentals
- Grand River Vacation rentals
- Northeast Ohio Vacation rentals
- St. Catharines Vacation rentals
- Rappahannock River Vacation rentals
- PNC Park
- Strip District
- Carnegie Mellon University
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Yellow Creek State Park
- Raccoon Creek State Park
- National Aviary
- Kennywood
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Fox Chapel Golf Club
- Carnegie Museum of Art
- Narcisi Winery
- Schenley Park
- Senator John Heinz History Center
- Children's Museum of Pittsburgh
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Randyland




