
Holiday rentals in Oakmont
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Oakmont
Guests agree: these stays are highly rated for location, cleanliness and more.

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.

1 Bed, idyllic, stadiums, free parking, & Pets OK
Here's a quiet hideaway. Book the apartment, and reserve a fine meal at a nearby restaurant, and walk to the nearby park. For the price of a hotel room, you get living and sunrooms, a complete kitchen with parking, washing, ironing, and excellent internet access. You are close to concerts, parks, museums, stadiums, AGH, and fine restaurants. This apartment is a great center to explore downtown and the Northside of Pittsburgh. You and your pet will like the large park, only a 1/2 block away.

East End Gem | Your Home Away from Home
This bright, stylish, and comfortable space, designed by an HGTV producer! With a fully remodeled kitchen and bathroom, cozy beds, and inviting rooms, this home offers the perfect home away from home. Conveniently located within 20 minutes of everything Pittsburgh has to offer, including sports fields, rivers, bridges, shopping, museums, historical sites, music venues, universities, and more! Whether you're here for business or pleasure, you'll find everything you need for a relaxing stay.

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 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.

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.

PRIVATE FULL STUDIO (G2)
This Studio is for anyone needing a neat, clean, cool place to stay with a queen bed, a sleeper sofa (almost queen size), a full kitchen and a full bathroom (shower only) with a private entrance on the 2 nd 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)

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

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

*STEAM SAUNA* - Steps to butler
Enjoy a stylish experience just steps from all that lawrenceville has to offer! 5 star restaurants, boutiques, and gastropubs! You will love having easy access to wifi as well as Prime video on the 60 inch TV! Fully equipped kitchen is at your service as well as delicious complimentary coffee! Dive into your push queen sized bed for a fantastic night sleep! Enjoy the shared sauna as a way to relax and reap the health benefits of heat therapy!

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

Spacious bedroom, The Run

Basement apartment with private entrance and bath

Sunny, spacious apartment in beautiful Regent Sq.

2 Bedroom house in Churchill 7-mile from downtown

The Fawn Room - Double Bed

1 Bed Point Breeze N, Bakery Sq.

A private & spacious room in Northeast Pittsburgh

The Maverick by Kasa | Steps to Bakery Square
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 $88 SGD per night before taxes and fees

Verified guest reviews
Over 930 verified reviews to help you choose

Family-friendly holiday rentals
50 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
70 of Oakmont holiday 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!
Destinations to explore
- Greater Toronto and Hamilton Area Holiday rentals
- Greater Toronto Area Holiday rentals
- Washington Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Northeast Ohio Holiday rentals
- St. Catharines Holiday rentals
- Rappahannock River Holiday rentals
- PNC Park
- Carnegie Mellon University
- Seven Springs Mountain Resort
- Strip District
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Acrisure Stadium
- Idlewild & SoakZone
- Point State Park
- National Aviary
- Kennywood
- Raccoon Creek State Park
- Ohiopyle State Park
- Phipps Conservatory and Botanical Gardens
- University Of Pittsburgh
- Schenley Park
- Carnegie Museum of Art
- Children's Museum of Pittsburgh
- David Lawrence Convention Center
- Randyland
- Senator John Heinz History Center
- Cathedral of Learning
- Stage AE
- Carnegie Science Center




