
Holiday houses in Oakmont
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Top-rated holiday rentals in Oakmont
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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!

The Sycamore BnB @ 10.7 Marina
Stay above 10.7 Marina on the Allegheny River, in Verona, PA, a little river town about 10.7 miles upriver from Downtown Pittsburgh. Enjoy a complementary kayak frompad board or canoe rental to enjoy a river adventure or dip in the Allegheny to cool off. Create your own river adventure to Sycamore Island, or Plum Creek to explore. You can also take it easy and hang out on the deck with panoramic views of this “lake like view” and enjoy the many sunsets. Eat, drink and shop many local spots.

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.

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.

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.

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.

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.

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

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, Acrisure Stadium, Rivers Casino, and PNC Park. 5 minutes from PA Turnpike. Must be able to climb steps.
Popular amenities for Oakmont holiday rentals
Other great holiday rentals in Oakmont

Basement apartment with private entrance and bath

Master Bed Room with Private Bath

Bloomfield/Pittsburgh @G Cozy & Bright Private BD

Cozy room in historic farmhouse

Little Paris-Twin Bed Room

Bedroom 1 in Quaint Rustic Home (Blue Key)

Cozy warm lovely Squirrel Hill free park & wifi

Phenom cozy ROOM ctrl to DT, UPMC, Oakland, Bkr Sq
Frequently Asked Questions
Are there vacation rentals with a dedicated workspace in Oakmont?
Yes! Work meets play with ease at over 20 vacation rentals in Oakmont featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Oakmont?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with air conditioning, over 50 homes with free parking, over 50 homes with wifi, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do bed and breakfast rentals in Oakmont have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oakmont have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Oakmont?
Four-legged friends are welcome in Oakmont. Choose from more than 10 vacation rentals for guests traveling with pets.
Do bed and breakfast rentals in Oakmont have free parking?
Absolutely! We offer over 10 bed and breakfast rentals with free parking in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Oakmont have a kitchen?
Absolutely! We offer over 50 house rentals with a kitchen in Oakmont. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Oakmont?
Oakmont has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Oakmont?
Experience the best of Oakmont with our house rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Where should I stay in Oakmont?
Make yourself at home in Oakmont by choosing from our most frequently booked neighborhoods. We have over 380 vacation rentals in Upper Oakmont, over 380 vacation rentals in Dark Hollow Road, and over 310 vacation rentals in Lower Oakmont.
Quick stats about holiday rentals in Oakmont

Total holiday rentals
Explore 70 holiday rentals in Oakmont

Nightly prices starting at
Oakmont holiday rentals start at $121 NZD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
70 of Oakmont holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oakmont rentals

4.9 Average rating
Oakmont stays are highly rated by guests—averaging 4.9 out of 5!
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- 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
- Children's Museum of Pittsburgh
- Senator John Heinz History Center
- Bella Terra Vineyards
- Laurel Mountain Ski Resort
- Randyland




