
Vacation rentals in Oakmont
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Top-rated vacation 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.

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.

The Pop Art Studio - Cool, Convenient & Commutable
Conveniently located off of highway 376, tucked away in a Swissvale neighborhood, this newly renovated studio has everything you need for a visit to Pittsburgh. The unique interior design and lovely private patio make our apartment stand out from the rest. Ground floor- no steps required! Parking is free on our street. Enjoy proximity to all Pittsburgh has to offer! Please note, we are in a transitioning neighborhood that's a melting pot of young professionals and longtime residents.

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.

Hot Tub, King Bed, Cabin Vibes in Lawrenceville!
With cozy cabin vibes, exposed brick, and designer touches, this romantic getaway is perfect for couples or a relaxing stay. Escape to a rustic-modern retreat in the heart of Lawrenceville, just one block from Butler Street! Unwind in the private hot tub, snuggle up on the couch by the fireplace, or explore the city's best dining and nightlife just steps away. Completely remodeled in January 2025 with luxe amenities—book now for an unforgettable stay!

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

PRIVATE MINI STUDIO (D1)
This Mini Studio is for anyone needing a neat, clean, cool place to stay. It has a new queen bed, sleeper sofa, a kitchenette and a full bathroom with a private entrance on the 3rd floor of a beautiful 1890s Pittsburgh mansion. It's the size of a large room and works very well with guests 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).

Free parking ⁕ Affordable Stay ⁕ 5 min to Downtown
Cozy 450 sq ft 1-bedroom with everything you need and nothing you don't. This private access unit has a newly renovated bathroom and kitchen. Located near downtown Pittsburgh but in a suburban-feeling neighborhood. Walking distance from a grocery store, some great local food options, and the public transit right at your door. Free and easy parking readily available. An affordable and comfortable way to experience the Burgh!
Popular amenities for Oakmont vacation rentals
Other great vacation rentals in Oakmont

Basement apartment with private entrance and bath

The Fawn Room - Double Bed

Oakland/University @C Modern & Stylish Private Bd

Cozy home in Spring Hill with a Single bedroom.

Cozy Private Room

Cozy warm room in lovely Squirrel Hill

Phenom cozy ROOM ctrl to DT, UPMC, Oakland, Bkr Sq

Castle Shannon's Home Away From Home.
Frequently Asked Questions
Are there house rentals with a dedicated workspace in Oakmont?
Yes! Work meets play with ease at over 20 house rentals in Oakmont featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for Bed And Breakfast Rentals in Oakmont?
Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Oakmont have wifi?
Absolutely! We offer over 50 house 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 house rentals in Oakmont?
Four-legged friends are welcome in Oakmont. Choose from more than 10 house 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 house rentals in Oakmont?
Oakmont has more than 40 family-friendly house rentals. 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 370 vacation rentals in Dark Hollow Road, over 310 vacation rentals in Lower Oakmont, and over 370 vacation rentals in Upper Oakmont.
Quick stats about vacation rentals in Oakmont

Total vacation rentals
Explore 70 vacation rentals in Oakmont

Nightly prices starting at
Oakmont vacation rentals start at $99 CAD per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 of Oakmont vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, 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
- Carnegie Mellon University
- Strip District
- Fallingwater
- Seven Springs Mountain Resort
- Pittsburgh Zoo & PPG Aquarium
- Idlewild & SoakZone
- Oakmont Country Club
- Yellow Creek State Park
- Raccoon Creek State Park
- Kennywood
- National Aviary
- Ohiopyle State Park
- Fox Chapel Golf Club
- Phipps Conservatory and Botanical Gardens
- Point State Park
- Narcisi Winery
- Carnegie Museum of Art
- Schenley Park
- Senator John Heinz History Center
- Bella Terra Vineyards
- Children's Museum of Pittsburgh
- Cathedral of Learning
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