Chipley Vacations from $916

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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.
BEAUTIFUL CONDO ON THE BEACH, UNIT 1708

BEAUTIFUL CONDO ON THE BEACH, UNIT 1708

4.5 out of 5
Miramar Beach
Save 100% on your flight
per person
Oct 5 - Oct 10
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
10/10 Exceptional! (21 reviews)
Super nice. Owner was extremely responsive and very easy to deal with.

Reviewed on Aug 10, 2025

Seacrest Beach Modern Tranquility Walk to Beach

Seacrest Beach Modern Tranquility Walk to Beach

3 out of 5
Rosemary Beach
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
No reviews
Halcyon Dayz by Avantstay New Build w/ Pool Access

Halcyon Dayz by Avantstay New Build w/ Pool Access

3 out of 5
Save 100% on your flight
per person
Sep 30 - Oct 4
found 13 hours ago
Roundtrip flight included
Miami (MIA) to Panama City (ECP)
No reviews
Chic Shack by Avantstay Private Pool, Walk to Beach, Sleeps 13!

Chic Shack by Avantstay Private Pool, Walk to Beach, Sleeps 13!

3 out of 5
Save 100% on your flight
per person
Oct 9 - Oct 13
found 21 hours ago
Roundtrip non-stop flight included
Miami (MIA) to Panama City (ECP)
No reviews
Beach Bike Cottage by Avantstay Walk to Beach, Resort Pool

Beach Bike Cottage by Avantstay Walk to Beach, Resort Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
No reviews
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Discover the most popular places to visit in Chipley

Falling Waters State Park

Commune with nature and explore the great outdoors at Falling Waters State Park during your travels in Chipley. Stroll along the lakeside or discover the area's waterfalls.

Falling Waters State Park

Chipley Hotel Deals

Palmetto Beachfront Hotel, a By the Sea Resort

Palmetto Beachfront Hotel, a By the Sea Resort

2 out of 5
17255 Front Beach Road, Panama City Beach, FL
Fully refundableReserve now, pay when you stay
$63 nightly
The price is $72 total per night from Aug 19 to Aug 20
$72 total
Aug 19 - Aug 20
Total includes taxes and fees
7.8/10 Good! (1,744 reviews)
"Great location ,on the beach ,easy to dining and shopping."

Reviewed on Aug 15, 2025

Palmetto Beachfront Hotel, a By the Sea Resort
Radisson Beachfront Hotel - Panama City Beach

Radisson Beachfront Hotel - Panama City Beach

3 out of 5
15325 Front Beach Road, Panama City Beach, FL
Fully refundable
$85 nightly
The price is $96 total per night from Aug 25 to Aug 26
$96 total
Aug 25 - Aug 26
Total includes taxes and fees
7/10 Good! (2,320 reviews)
"We would stay again"

Reviewed on Aug 17, 2025

Radisson Beachfront Hotel - Panama City Beach
Embassy Suites by Hilton Panama City Beach Resort

Embassy Suites by Hilton Panama City Beach Resort

3.5 out of 5
16006 Front Beach Road, Panama City Beach, FL
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $142 total per night from Sep 1 to Sep 2
$142 total
Sep 1 - Sep 2
Total includes taxes and fees
8.4/10 Very Good! (934 reviews)
"Bed not to comfortable the breakfast was ok if they could just add some seasoning like season all are a little salt food is bland if from New Orleans"

Reviewed on Aug 16, 2025

Embassy Suites by Hilton Panama City Beach Resort
See all 7,813 properties in Chipley
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.

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Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $916 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.