
Holiday rentals in Oakmont
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Top-rated holiday rentals in Oakmont
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Pittsburgh, PA - North Side
Keep it simple at this peaceful and centrally-located place. This two bedroom single family home is in an optimal location for access to all Pittsburgh has to offer. Located 2 miles from Pittsburgh's downtown area and Strip District, 5 minutes from PNC Park and Heinz Field, 10 minutes from PPG Paints Arena and UPMC Hospitals, and 15 minutes from CMU, University of Pittsburgh, and Duquesne University. Minutes from Garden Cafe coffee shop, Threadbare Cider House and plenty of bars and restaurants.

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.

Walkable Lawrenceville, Designer “Tiny Living”
The Nesting Box is an ideal space to return to and recharge in after “free-ranging” locally. Comfortable, cool, and centrally located to the best of Butler Street. Designers collaborated to maximize the minimal space with creative comforts for experiencing "tiny living". Our shipping container addition led us to have 2 front 🚪. We welcome guests to our on-street private guest suite. Urban family homestead with 1 🐈⬛, 2 🐕, and 3 🐓 that resided with us for 5 years (recently rehomed to farm).

Artsy Apt in Lawrenceville with deck & parking
One bedroom, one bathroom 2nd floor apartment located in Lower Lawrenceville with easy access to downtown, the Strip District, Shadyside, and our own very walkable neighborhood. You'll be able to park right behind the property and walk to a ton of coffee shops, yoga, art galleries, shops, and restaurants. There is a washer/dryer in the bathroom. The kitchen has a dishwasher. The second bed is a pullout couch in the living room. Every window has a shade you can pull down to keep out the light.

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.

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.

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.

Shadyside/Pittsburgh, Modern & Cozy 1BD w/Prkng
Modern and family oriented 1 Bedroom apartment with a central location in Shadyside, located minutes to UPMC Hospitals, Universities, Walnut St. Enjoy the proximity to shopping, bars & restaurants. This apartment features 1 Bedroom & Dining area and FREE Parking. Stylishly setup, our home features high speed internet and Smart Home Security system for additional safety of our guests. This place is suitable for families, executives, expats and this is NOT a party place.

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
Popular amenities for Oakmont holiday rentals
Other great holiday rentals in Oakmont

Modern Studio Close to Popular Pittsburgh Sights

Cozy! Micro Loft apartment Shadyside, sleeps 1

Allegheny River Aqua Villa

Oakmont Area - Carriage House

The Pitt Stop

Mid-century modern Lustron & Japanese garden

Aspinwall 1 bedroom Apartment

Ranch Home: Cozy & Modern!
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 € 59 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!
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- PNC Park
- Carnegie Mellon University
- Strip District
- Seven Springs Mountain Resort
- Fallingwater
- Pittsburgh Zoo & PPG Aquarium
- Acrisure Stadium
- Idlewild & SoakZone
- Kennywood
- Raccoon Creek State Park
- National Aviary
- Ohiopyle State Park
- Point State Park
- Phipps Conservatory and Botanical Gardens
- Schenley Park
- Carnegie Museum of Art
- Children's Museum of Pittsburgh
- University Of Pittsburgh
- Senator John Heinz History Center
- Randyland
- David Lawrence Convention Center
- Cathedral of Learning
- Carnegie Science Center
- Stage AE




