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A skate park with ramps and a gravel path.
Photo by Peter Facey
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Fair Oak Vacations from $1,299

Book a Hotel + Flight or Car together to unlock savings

The Latest Fair Oak Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Exterior
    Oct 6 - Oct 12

    Best Western Chilworth Manor Hotel + Flight

    Southampton
    5 nights
    3.0 star property
    8.0/10 - Very Good (1,000 reviews)
    "Beautiful old building, lovely grounds Would stay again"
    Reviewed July 29, 2026
    Roundtrip • Philadelphia (PHL) - Southampton (SOU)
    PHL - SOU • 2 stops SOU - PHL • 1 stop
    $1,414
    $1,299
    per traveler
    found 1 day ago
    Best Western Chilworth Manor Hotel
  • House | 5 bedrooms
    Oct 6 - Oct 12

    Southampton Getaway Huge Home Garden Sleeps 10 + Flight

    Southampton
    5 nights
    2.0 star property
    Roundtrip • Philadelphia (PHL) - Southampton (SOU)
    PHL - SOU • 2 stops SOU - PHL • 1 stop
    $2,730
    $2,460
    per traveler
    found 1 day ago
    Southampton Getaway Huge Home Garden Sleeps 10
  • Deluxe Double Room | Premium bedding, memory foam beds, minibar (free items), in-room safe
    Oct 6 - Oct 12

    No.4 Carlton Hotel + Flight

    The Polygon
    5 nights
    4.0 star property
    9.6/10 - Exceptional (156 reviews)
    "I booked this room based off other recommendations and so glad I did. What a beautiful boutique stay. The rooms were large, clean, well designed with excellent craftsmanship. Breakfast was included. Would definitely go back."
    Reviewed July 30, 2026
    Roundtrip • Philadelphia (PHL) - Southampton (SOU)
    PHL - SOU • 2 stops SOU - PHL • 1 stop
    $2,060
    $1,896
    per traveler
    found 1 day ago
    No.4 Carlton Hotel
  • Basic Room | In-room dining
    Oct 6 - Oct 12

    Perfect for contractors + Flight

    Southampton
    5 nights
    3.5 star property
    10/10 - Exceptional (1 review)
    "Really nice house, table football etc for the kids, nice back garden and well-equipped kitchen. Really happy"
    Reviewed August 31, 2025
    Roundtrip • Philadelphia (PHL) - Southampton (SOU)
    PHL - SOU • 2 stops SOU - PHL • 1 stop
    $1,819
    $1,693
    per traveler
    found 1 day ago
    Perfect for contractors
  • Exterior
    Oct 6 - Oct 12

    Woodlands Lodge Hotel + Flight

    Southampton
    5 nights
    3.0 star property
    8.6/10 - Excellent (366 reviews)
    "Lovely location. Noisy from 7am onwards due to delivery vehicle bin Lorrie’s. Nice garden friendly staff. Needs a little investment to update"
    Reviewed August 2, 2026
    Roundtrip • Philadelphia (PHL) - Southampton (SOU)
    PHL - SOU • 2 stops SOU - PHL • 1 stop
    $1,461
    $1,368
    per traveler
    found 1 day ago
    Woodlands Lodge Hotel

Fair Oak Hotel Deals

Exterior

Leonardo Hotel Southampton

Leonardo Hotel Southampton
4.0 star property
5.9 mi from Fair Oak
8.6 out of 10, Excellent, (1,416 reviews)
"Easy access , clean and near everything"
$78 nightly
The price is $93
Aug 31 - Sep 1
Total with taxes and fees
Leonardo Hotel Southampton
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.
See all properties in Fair Oak

Frequently Asked Questions

How much does a Fair Oak vacation package cost?

You'll find cheap prices from $1,299 on Expedia for your Fair Oak escape. However, a range of factors like the season, length of stay and your choice of hotel will influence how much your vacation to Fair Oak costs.

What are the cheapest months to go to Fair Oak?

You can typically find lower rates and better availability in January, June and December. Take a look at our cheap Fair Oak vacation packages and you could score some great off-season discounts.

How many days is enough for Fair Oak?

Usually, a handful of days is enough to check out the top sights during your Fair Oak vacation. However, if you prefer to have time to chill out or take day tours, consider extending your itinerary.

How to find the best Fair Oak package deals?

Begin your search for a Fair Oak package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor 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 ideal Fair Oak package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Fair Oak adventure underway.

Is it cheaper to book a Fair Oak vacation as a package?

You can enjoy significant savings on your next Fair Oak getaway by booking a personalized vacation package. Click on the "Package" heading, then select your destination and travel dates to see the best hotel prices and airfares. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Fair Oak?

If you have your Fair Oak travel dates finalized, book as early as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spur-of-the-moment adventures? Our last-minute deals are great for jetting off on a whim.

Does Expedia offer Book Now, Pay Later Fair Oak vacation packages?

If you're anything like us, you love traveling the world but are not a fan of the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Fair Oak break across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.

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