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A waterfall cascading over a rocky cliff surrounded by lush green ferns and foliage.

Chipley Vacations from $744

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The Latest Chipley Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Private beach, white sand, sun loungers, beach umbrellas
    Sep 20 - Sep 24

    Studios at Fontainebleau Terrace + Flight

    Panama City Beach
    4 nights
    3.5 star property
    7.0/10 - Good (4 reviews)
    "The location is excellent, the beach is great. There's a nice restaurant nearby. The room is your typical motel room with a kitchenette. No balcony or private window."
    Reviewed May 25, 2026
    Roundtrip • Philadelphia (PHL) - Panama City (ECP)
    PHL - VPS • 1 stop VPS - PHL • 1 stop
    Save 100% on your flight
    $1,139
    $744
    per traveler
    found 19 hours ago
    Studios at Fontainebleau Terrace
  • Apartment (2 Bedrooms) | Front of property
    Oct 5 - Oct 9

    South Shore 30A by Avantstay Gulf View Pool + Flight

    Rosemary Beach
    4 nights
    3.0 star property
    6.0/10 - (1 review)
    "The property has an amazing location, but at a price that you sleep on a dirty bed. You can notice the level of cleanliness that the AC filter was dirty. Check your beds before going to bed. It had lots of hairs from previous guest"
    Reviewed October 2, 2025
    Roundtrip • Denver (DEN) - Panama City (ECP)
    DEN - VPS • 1 stop VPS - DEN • 1 stop
    Save 100% on your flight
    $3,139
    $2,343
    per traveler
    found 1 day ago
    South Shore 30A by Avantstay Gulf View Pool
  • House (5 Bedrooms) | Interior
    Oct 5 - Oct 9

    Southern Shores by Avantstay Seacrest Beach Resort Pool + Flight

    Rosemary Beach
    4 nights
    3.0 star property
    10/10 - Exceptional (1 review)
    "Good place to be"
    Reviewed December 8, 2025
    Roundtrip • Denver (DEN) - Panama City (ECP)
    DEN - VPS • 1 stop VPS - DEN • 1 stop
    Save 100% on your flight
    $2,248
    $1,735
    per traveler
    found 1 day ago
    Southern Shores by Avantstay Seacrest Beach Resort Pool
  • House (5 Bedrooms) | Interior
    Oct 5 - Oct 9

    Amour La Mer by Avantstay Rooftop Patio, Pool Access, Walk to Beach + Flight

    Rosemary Beach
    4 nights
    3.0 star property
    Roundtrip • Denver (DEN) - Panama City (ECP)
    DEN - VPS • 1 stop VPS - DEN • 1 stop
    Save 100% on your flight
    $2,469
    $1,915
    per traveler
    found 1 day ago
    Amour La Mer by Avantstay Rooftop Patio, Pool Access, Walk to Beach
  • Apartment (2 Bedrooms) | Interior
    Aug 20 - Aug 26

    Blue Marlin by Avantstay Beachfront w/ Views, Pool Access, Beach Chairs + Flight

    Sunnyside
    6 nights
    3.0 star property
    Roundtrip • New York (EWR) - Panama City (ECP)
    EWR - VPS • 1 stop VPS - EWR • 1 stop
    Save 100% on your flight
    $2,746
    $2,134
    per traveler
    found 1 day ago
    Blue Marlin by Avantstay Beachfront w/ Views, Pool Access, Beach Chairs

Discover the most popular places to visit in Chipley

A waterfall cascading down a moss-covered rock in a forested area.

Falling Waters State Park

8.6/10 (48 reviews)
Florida's tallest waterfall plunges 73 feet into a cylindrical sinkhole before disappearing underground. Stroll the boardwalks through pine forests and fern-covered sinkholes for the most dramatic views after rainfall.

Chipley Hotel Deals

Desk, laptop workspace, iron/ironing board, WiFi (free)

Quality Inn Chipley I-10 at Exit 120

Quality Inn Chipley I-10 at Exit 120
2.5 star property
2.2 mi from Chipley
7.6 out of 10, Good, (783 reviews)
"The place is poorly kept, the rooms are dirty, the sheets are stained, the bathrooms are old and stained, and the tile repair looked like a kid did it with brown grout. I even found a live roach and a dead one. I booked it for two nights but left the next day. I got a refund for the second night, but when I told the front desk person about all of this, he just said the roaches weren't roaches, they were "bugs"? I definitely don't recommend this place."
$78 nightly
The price is $86
Jul 21 - Jul 22
Total with taxes and fees
Quality Inn Chipley I-10 at Exit 120
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 Chipley

Frequently Asked Questions

How much does a Chipley vacation package cost?

You'll find cheap prices from $744 on Expedia for your Chipley escape. However, factors like your choice of hotel, the season and length of stay will determine how much your vacation to Chipley costs.

What are the cheapest months to go to Chipley?

If you're hoping to snag a cheap Chipley vacation package, consider visiting in August, September and October. You're likely to find better prices on hotels and flights during these quieter months — ideal for a budget-friendly break.

How many days is enough for Chipley?

The ideal duration for your Chipley vacation depends on what you'd like to do and see. Usually, a few days to a week will give you time to hit all the top sights and discover some hidden gems along the way.

How to find the best Chipley package deals?

Begin your search for a Chipley package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Popular locations," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Chipley package deal right away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Chipley getaway off to a flying start.

Is it cheaper to book a Chipley vacation as a package?

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

When to book a vacation package to Chipley?

If you're considering an impromptu Chipley vacation, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can find sensational deals on your flights and hotels by booking well in advance.

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

If you're like us, you love going away but don't love the price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Chipley trip across 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure great vacation packages with payment plans as soon as you spot them.

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