
Chipley Vacations from $652
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Your Chipley Vacation
Experience the unique character and personality of Chipley with a tailor-made Chipley vacation package. From its small-town feel to its friendly locals and beyond, you'll never have a dull moment in this city. Your trip to Chipley has to include a little sightseeing. Falling Waters State Park is a good place to start. Expedia is here to help you escape your routine. Tailor your vacation to Chipley to suit your style of travel, whatever that may be!
The Latest Chipley vacation packages
Price found within the past 48 hours. Click for updated prices.

Landing Apartments - Freeport Near Santa Rosa Beach
$652
per person
Oct 1 - Oct 4
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to Panama City (ECP)
10/10 Exceptional! (1 review)
This was a very nice apartment for rent.”The Landing” is a company who rents apartments from a complex and furnishes the apartments to rent out for one night or for a month or more. Everything was spot on! Some places you rent for short term, they ask you to wash your bedding etc before leaving. None of that! It’s a very quiet community, dog park, pool. However, you cannot get help from the apartment complex with your codes etc. It’s a sublet apartment. Codes and wifi you must contact “The Landing” and not Expedia or the “Arcadia apartment office”
When you check in to the Landing online, they will take you through everything. Thankfully I did screenshot each page I checked because I was never able to access their app that they ask you to download and use. You need to save the key code for the front door that you are given. Save it because everytime you need to go in the building, you must use. Then you will have a code for your apartment door.
The door has a “smart door lock”. We had never seen one of these. We were totally stumped at first. They don’t explain it. It’s an all black door knob and all you need to do is touch the knob and it will light up with white numbers like a clock and you punch in the code to the apartment. You do need to turn the deadbolt away from the door jam to unlock. When you leave, make sure you deadbolt the door.
Reviewed on Apr 30, 2026

Club Wyndham Panama City Beach
$900
per person
Nov 7 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Panama City (ECP)
8.4/10 Very Good! (393 reviews)
All was clean and very well set up from arrival to departure, help is everywhere at the tap of your phone. Only thing I had trouble with were the grills didnt get hot enough but just finished in our room.the whole place was great and staff so helpful and caring for your needs. Will be back next year. 🙂
Reviewed on Aug 29, 2026


South Shore 30A by Avantstay Gulf View Pool
Rosemary Beach
$1,697
per person
Nov 20 - Nov 23
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
6/10 (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 on Oct 2, 2025

Stay near popular Chipley attractions

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.

Pal's Park
Pal's Park features 37.7 acres of sports facilities and scenic trails in Chipley. Enjoy tennis, watch local baseball tournaments, or take a morning jog through the natural landscape.
Lucas Lake
8.4/10 (6 reviews)
Lucas Lake offers a serene freshwater escape surrounded by lush Florida greenery. Cast a line at dawn when the waters are calmest and wildlife is most active.
Moss Hill Methodist Church
This 1857 rural church stands as one of Florida's oldest, featuring rare glass windows from the Civil War era. Explore the heart pine structure and historic cemetery where early settlers rest in peaceful Holmes Valley.
Chipley Hotel Deals

Chateau Beachfront Hotel, A By The Sea Resort
12525 Front Beach Rd Panama City Beach FL
Fully refundableReserve now, pay when you stay
$64 nightly
$73 total
Sep 1 - Sep 2
Total with taxes and fees

Radisson Beachfront Hotel - Panama City Beach
15325 Front Beach Road Panama City Beach FL
Fully refundable
$85 nightly
$97 total
Sep 2 - Sep 3
Total with taxes and fees
7/10 Good! (3,032 reviews)
"The elevators were not working properly, the wait was in excess of 15 minutes on more than one occasion . There is not enough parking. You will be charged an incidental fee of $20 per day for nothing on top of your hotel room fee . The table in the room had not been cleaned and had something dried ..."
Reviewed on Aug 31, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
15505 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
$139 nightly
$157 total
Sep 29 - Sep 30
Total with taxes and fees
8.8/10 Excellent! (2,779 reviews)
"Room was very clean, clean lobby and breakfast area. Continental breakfast was ok. Great beach view! I love the Hilton brand! Would definitely stay there again!"
Reviewed on Aug 30, 2026
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.
Find the Best Chipley Vacation Packages
Chipley Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,600 |
Max Temp Winter | 65ºF |
Max Temp Summer | 90ºF |
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Frequently asked questions
How much does a Chipley vacation package cost?
You'll find cheap prices from $652 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


















