A bridge with illuminated lights crossing a river, with a city skyline in the background.

Oakmont Vacations from $451

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Your Oakmont Vacation

The stress-free way to experience this interesting city is with a tailor-made Oakmont vacation package. Stay in the neighborhood of Lawrenceville, which is great for nightlife, bars and pubs and dining or go someplace else — our packages are all about you. If taking in sights is on the cards during your trip to Oakmont, swing by well-known attractions like Pittsburgh Zoo and PPG Aquarium, Sri Venkateswara Temple and Bakery Square. Whoever you're going away with and whatever your budget, your dream Oakmont vacation is only clicks away with Expedia.

The Latest Oakmont Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 26 - Dec 28

    Stay Pittsburgh + Flight

    Downtown Pittsburgh
    2 nights
    2.0 star property
    8.0/10 - Very good (346 reviews)
    Roundtrip • New York (EWR) - Pittsburgh (PIT)
    EWR - PIT • Nonstop PIT - EWR • Nonstop
    $555
    $451
    per traveler
    found 1 day ago
    Stay Pittsburgh
  • Feb 4 - Feb 8

    THE GRANDEUR ESTATE + Flight

    Greensburg
    4 nights
    3.5 star property
    10/10 - Exceptional (27 reviews)
    "Loved the room and the history about the Estate. Tony and his staff were great!"
    Reviewed October 11, 2026
    Roundtrip • Houston (IAH) - Pittsburgh (PIT)
    IAH - PIT • Nonstop PIT - IAH • Nonstop
    $1,191
    $982
    per traveler
    found 21 hours ago
    THE GRANDEUR ESTATE
  • Feb 4 - Feb 8

    The Lodge at Chalk Hill + Flight

    Chalkhill
    4 nights
    2.5 star property
    9.0/10 - Wonderful (448 reviews)
    Roundtrip • Houston (IAH) - Pittsburgh (PIT)
    IAH - PIT • Nonstop PIT - IAH • Nonstop
    $639
    $529
    per traveler
    found 21 hours ago
    The Lodge at Chalk Hill
  • Feb 4 - Feb 8

    South Broadway Manor + Flight

    Scottdale
    4 nights
    3.0 star property
    9.8/10 - Exceptional (131 reviews)
    Roundtrip • Houston (IAH) - Pittsburgh (PIT)
    IAH - PIT • Nonstop PIT - IAH • Nonstop
    $815
    $675
    per traveler
    found 21 hours ago
    South Broadway Manor
  • Jan 15 - Jan 18

    Fairmont Pittsburgh + Flight

    Downtown Pittsburgh
    3 nights
    4.5 star property
    8.8/10 - Excellent (1,004 reviews)
    "Garage parking was super convenient and easy, rooms were clean and very comfortable."
    Reviewed November 8, 2026
    Roundtrip • Los Angeles (LAX) - Pittsburgh (PIT)
    LAX - PIT • Nonstop PIT - LAX • Nonstop
    $893
    $747
    per traveler
    found 1 day ago
    Fairmont Pittsburgh

Where to stay in Oakmont

Discover the charm of Oakmont, a family-friendly city perfect for outdoor activities and sports. Explore the vibrant oakmont city center and nearby oakmont districts. Use an online map to navigate to downtown Pittsburgh, where you can enjoy urban art and business vibes, especially during high season.

Pittsburgh

For travelers seeking a vibrant city experience, Pittsburgh offers a perfect base to explore its dynamic attractions. Visitors can enjoy the educational atmosphere of the University of Pittsburgh, unwind at the scenic PNC Park, and catch a thrilling event at the PPG Paints Arena. Oakmont is conveniently located within Pittsburgh, making it easy to access these highlights. With a mix of business, family-friendly activities, and outdoor adventures, Pittsburgh is a smart choice for your hotel booking.

Harmarville

Experience the charm of Harmarville, an excellent hub for families and weekend getaways eager to explore nearby attractions like the University of Pittsburgh, Sri Venkateswara Temple, and Monroeville Convention Center. This vibrant village offers access to shopping malls and urban parks, providing a delightful mix of leisure and city life. Located about 1.0 mile drive from Oakmont, Harmarville is a smart choice for travelers looking to enjoy a variety of activities while staying close to the excitement.

Verona

Make your vacation planning effortless by staying in Verona, a haven for family travelers and weekend getaways thanks to its proximity to attractions like the University of Pittsburgh and the Monroeville Convention Center. Enjoy outdoor activities at nearby national parks, or unwind at local golf courses. Just about a 1-mile drive from Oakmont, Verona offers a smooth transition for those looking to explore the area. Choosing Verona for your stay ensures a blend of relaxation and adventure.

Harmarville

Harmarville stands out as a prime spot for family travelers interested in exploring the vibrant culture and activities of Pittsburgh. With a shopping mall center, golf course, and an urban park nearby, families can enjoy a diverse range of experiences. Additionally, attractions like the University of Pittsburgh and the Monroeville Convention Center are just a short drive away, providing enriching educational and entertainment opportunities. Located about 2 miles away from Oakmont, Harmarville is a smart choice for your next hotel booking.

Fox Chapel

Travelers visiting the area often choose Fox Chapel, especially families and leisure seekers looking for a charming village experience. With its beautiful urban parks, the nearby University of Pittsburgh, and the vibrant Petersen Events Center, Fox Chapel offers plenty of opportunities for outdoor fun and cultural exploration. Located about 2 miles by car from Oakmont, it's an ideal base for those wanting to enjoy both local attractions and a peaceful retreat. Fox Chapel makes for a smart choice for your stay.

What to do in Oakmont

Oakmont Hotel Deals

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently Asked Questions

How much does an Oakmont vacation package cost?

Offering excellent value package deals from $451 on Expedia, you'll be pleasantly surprised at how much a vacation to Oakmont costs! Our packages mean less travel planning for you and greater savings.

What are the cheapest months to go to Oakmont?

If you'd like to score a cheap Oakmont vacation package, consider planning a trip in November, December and January. You'll typically find lower rates on flights and hotels during these months — ideal for a budget-friendly getaway.

How many days is enough for Oakmont?

The ideal duration of your Oakmont vacation depends on what you'd like to see and do. Typically, a few days to a week will give you enough time to check out all the main attractions and discover some hidden treasures along the way.

How to find the best Oakmont package deals?

Begin your search for an Oakmont package deal by entering your preferred trip dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Oakmont package deal straight away, simply tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakmont escape underway.

Is it cheaper to book an Oakmont vacation as a package?

You can enjoy significant savings on your next Oakmont break by booking a tailored vacation package. Check the "Package" heading, then select your destination and travel dates to see some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Oakmont?

Secure amazing discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Oakmont escape.

How to plan a trip to Oakmont?

  1. Choose when to travel: Check your diary and pack your bags. Your favorite time of year and the type of activities on offer will also help you decide when to vacation in Oakmont.
  2. Set a budget: Factor in expenses like transportation, flights and meals when calculating how much to save for your trip to Oakmont. Then, select a hotel that works with your budget, whether that's an economical option or a swankier getaway.
  3. Use our trip planning tool to explore Oakmont: Research every aspect of your trip to Oakmont with this handy planner. Invite friends or family to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Decide your trip length: Think about how long you'd like to spend discovering Oakmont. Plan your itinerary so you can get to all the activities and attractions you're interested in without rushing.
  5. Bundle your accommodations and airfare: Once you've settled on your trip dates and duration, book the right Oakmont vacation package for you.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on the highlights of Oakmont. Find all the exciting things to do in Oakmont with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Oakmont vacation packages?

Your Oakmont trip is meant to be an escape from your busy life, not a source of money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.