Chipley Vacations from $1,201

Book a Hotel + Flight or Car together to unlock savings

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.
Margaritaville Beach Cottage Resort PCB

Margaritaville Beach Cottage Resort PCB

4.5 out of 5
Save 100% on your flight
Price was $1,629, price is now $1,201 per person
$1,201
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Panama City (ECP)
9.4/10 Exceptional! (10 reviews)
Our cottage was beautiful . It had most of the amenities needed to be comfortable. The only t

Reviewed on Jan 1, 2026

Bellview by Avantstay Gorgeous Home w/ Multiple Balconies & Living Areas

Bellview by Avantstay Gorgeous Home w/ Multiple Balconies & Living Areas

3.5 out of 5
Sunnyside
Save 100% on your flight
Price was $2,712, price is now $1,998 per person
$1,998
per person
Apr 9 - Apr 14
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
No reviews
Blue Marlin by Avantstay Beachfront w/ Views, Pool Access, Beach Chairs

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

3 out of 5
Sunnyside
Save 100% on your flight
Price was $1,653, price is now $1,218 per person
$1,218
per person
Apr 9 - Apr 14
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Panama City (ECP)
No reviews
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The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
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Discover the most popular places to visit in Chipley

waterfall Falling Waters State Park green foliage limestone

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

Hampton Inn & Suites Panama City Beach-Beachfront

Hampton Inn & Suites Panama City Beach-Beachfront

2.5 out of 5
15505 Front Beach Road Panama City Beach FL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $116 total per night from Feb 26 to Feb 27
$116 total
Feb 26 - Feb 27
Total with taxes and fees
8.8/10 Excellent! (2,415 reviews)
We had a great experience! Great amenities and location! Only concern was the pool heater was not working so we weren’t able to swim. All good though as we enjoyed sitting on the side with our feet in. Our balcony provided an amazing ocean view! Breakfast was great each day! Staff were very friendly ...

Reviewed on Feb 19, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
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
$52 nightly
The price is $59 total per night from Feb 23 to Feb 24
$59 total
Feb 23 - Feb 24
Total with taxes and fees
7.8/10 Good! (2,209 reviews)
Great location. Thanks

Reviewed on Feb 20, 2026

Palmetto Beachfront Hotel, a By the Sea Resort
Hyatt Place Panama City Beach

Hyatt Place Panama City Beach

3 out of 5
15727 FRONT BEACH ROAD Panama City Beach FL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $105 total per night from Feb 26 to Feb 27
$105 total
Feb 26 - Feb 27
Total with taxes and fees
9.4/10 Exceptional! (1,671 reviews)
Courteous and rooms were very nice

Reviewed on Feb 19, 2026

Hyatt Place Panama City Beach
See all 7,781 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.

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 $1,201 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.