Holiday rentals in Cheswick

5 out of 5 average rating, 19 reviews

Home in Oakmont

3BR/2BA Hidden Gem on the Allegheny River

Looking for a hidden gem with river front views or maybe some kayaking up and down the Allegheny? Look no further! Located just feet from the Allegheny River is our newly remodeled 3BR/2BA duplex. Full kitchen, finished basement, sunporch and deck with beautiful views. Personal gate access to the river front. Within walking distance to the famous Oakmont bakery and majority of Oakmont's restaurants, bars and shopping. 5 minute drive to Oakmont Country Club. Unwind, relax and kick your feet up!

4.96 out of 5 average rating, 25 reviews

Houseboat in Blawnox

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!

4.93 out of 5 average rating, 159 reviews

Cabin in Pittsburgh

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.

4.86 out of 5 average rating, 293 reviews

Home in Verona

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.

Guest suite in Highland Park

4.98 out of 5 average rating, 241 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.

4.89 out of 5 average rating, 127 reviews

Home in Murrysville

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! 🚘

4.91 out of 5 average rating, 442 reviews

Flat in 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.

4.88 out of 5 average rating, 66 reviews

Home in Verona

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.

4.83 out of 5 average rating, 218 reviews

Flat in Bloomfield

PRIVATE MINI STUDIO IN BRIGHT NEW BASEMENT (A)

This Bright basement studio is for anyone needing a stylish, clean place to stay while visiting Pittsburgh. It has a new queen bed, sleeper sofa, desk, bar and a very large bathroom. It has a private entrance at the back of a beautiful 1890s Pittsburgh mansion. It works very well for travelers that are planning to work, or go out enjoying the city and come back to a safe, clean and comfy place to recharge for the night (not suitable for kids under 10).

5 out of 5 average rating, 6 reviews

Home in Point Breeze

HUGE Brand New Stylish Home ~ Parking~Theatre

BRAND NEW Single Family Home in centrally located Point Breeze neighborhood with room for the whole family! 6 Bedroom 3.5 Brand New Renovation with a HUGE Private Patio, fully stocked kitchen, 8 beds, loads of parking, and a 98" 4K Theatre Room! Walking distance to Bakery Square, Frick Park, East Liberty and Point Breeze shops and restaurants, a short drive to Pitt, CMU, Shadyside, Oakland, and all the stadiums & museums. Book your stay today!

4.93 out of 5 average rating, 271 reviews

Flat in Glenshaw

The Camera Stop

Open and bright private apartment located in the Fox Chapel area. Entire apartment was recently remodeled with all new furnishings and fixtures. We are located only 20 minutes from Downtown Pittsburgh and 15 minutes to Heinz Field, PPG Paints Arena, and PNC Park. This area is close to shopping, restaurants, grocery stores and the PA Turnpike. Jennifer is my office manager and your contact for any bookings or questions you may have. NO SMOKING

4.98 out of 5 average rating, 107 reviews

Guest house in Oakmont

Cozy Carriage House in Oakmont, PA

Freshly updated detached Carriage House with off-street parking. Sleeps 4 adults comfortably. Minutes from Oakmont Country Club. Walkable to Allegheny River Boulevard shops and Oakmont Bakery. Living room and Main Bedroom equipped with Smart TVs. Standard cable + HBO. Private patio area with seating. 20 minutes from Downtown Pittsburgh & 5 minutes from PA Turnpike. Must be able to climb steps.

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Other great holiday rentals in Cheswick

4.9 out of 5 average rating, 67 reviews

Private room in Gibsonia

Comfy unit with hot tub and parking space!

KathyRating, 5 stars6 days ago

Came in town for the US open and location was perfect. Next day went to Pittsburgh 12minutes away. The place is perfect for a two person get away.

Private room in Pittsburgh

4.98 out of 5 average rating, 571 reviews

Basement apartment with private entrance and bath

NourRating, 5 stars1 week ago

Michaels place felt right at home. The space was cozy and comfortable. My husband and I appreciated Michaels clear instructions, suggestions , and quick communication. I really enjoyed the snack options and as always, can never beat a massage chair. I highly recommend Michaels space. It was clean, cozy, and felt right at home. :)

Home in Apollo

5 out of 5 average rating, 5 reviews

Yew Arbor Cottage

JeremyRating, 5 stars6 days ago

Excellent stay. Exactly like the pictures. Kind and responsive host. The eggs from the neighbors chickens were an awesome bonus!

4.97 out of 5 average rating, 34 reviews

Private room in Verona

Cozy room in historic farmhouse

DaleRating, 5 stars4 days ago

John is was a terrific host who offered suggestions on local attractions and restaurants. He took a real interest in the purpose of our trip, the US Open golf tournament. We would look to stay at John’s Airbnb when we come to the Pittsburgh in the future!

4.84 out of 5 average rating, 101 reviews

Private room in Cheswick

A private & spacious room in Northeast Pittsburgh

HedwigRating, 5 stars8 months ago

This was my second time that I stayed there. Perfect for my needs! Would go there again if I travel to this area!

Private room in Pittsburgh

4.83 out of 5 average rating, 235 reviews

Cozy Private Room

JamesRating, 5 stars4 weeks ago

I've lost track of how many times I have stayed with Javier. This is my favorite go-to place to stay in Pittsburgh's North Hills. It is a quiet house in a quiet neighborhood. Most places in the North Hills are a short drive away. I feel like part of the family now. <SMILE>

Private room in New Kensington

4.83 out of 5 average rating, 12 reviews

One bedroom in a cozy house

BrittanyRating, 5 stars1 month ago

Frank was very responsive and met us at the door to let us in and review the code for the house and show us our room. We were only there to sleep and then had to leave early morning. But the stay was convenient and comfortable.