Chipley Vacations from $897

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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.
Club Wyndham Panama City Beach

Club Wyndham Panama City Beach

3.5 out of 5
Save 100% on your flight
Price was $1,269, price is now $897 per person
$897
per person
Apr 11 - Apr 18
found 2 hours ago
Roundtrip flight included
Boston (BOS) to Panama City (ECP)
8.4/10 Very Good! (372 reviews)
Beautiful view. Clean room. Nice staff

Reviewed on Jan 14, 2026

Steps to Rosemary Beach, Pool, Patio w/ Firepit The Salty Perch by Avantstay

Steps to Rosemary Beach, Pool, Patio w/ Firepit The Salty Perch by Avantstay

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,104, price is now $1,537 per person
$1,537
per person
Mar 20 - Mar 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Panama City (ECP)
No reviews
The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,503, price is now $1,112 per person
$1,112
per person
May 3 - May 6
found 24 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Panama City (ECP)
9.4/10 Exceptional! (188 reviews)
We had the best experience

Reviewed on Feb 2, 2026

Out of Office Beaches Private Pool, Steps to Beach Sleeps 15

Out of Office Beaches Private Pool, Steps to Beach Sleeps 15

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,175, price is now $2,366 per person
$2,366
per person
Mar 22 - Mar 26
found 20 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Panama City (ECP)
No reviews
Isle Be Back by Avantstay Pool, 2blocks to Beach

Isle Be Back by Avantstay Pool, 2blocks to Beach

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $1,721, price is now $1,292 per person
$1,292
per person
Mar 20 - Mar 23
found 24 hours ago
Roundtrip flight included
Boston (BOS) to Panama City (ECP)
No reviews
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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

4/5(19 reviews)

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
$52 nightly
The price is $59 total per night from Feb 9 to Feb 10
$59 total
Feb 9 - Feb 10
Total with taxes and fees
7.8/10 Good! (2,187 reviews)
The room was clean and the people who work there is great people but the deposit was a little bit aggravation to get back.

Reviewed on Feb 5, 2026

Palmetto Beachfront Hotel, a By the Sea Resort
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
$94 nightly
The price is $106 total per night from Feb 22 to Feb 23
$106 total
Feb 22 - Feb 23
Total with taxes and fees
8.6/10 Excellent! (2,385 reviews)
Lovely and friendly young woman checked us in! Explained hotel layout and amenities ! Great view with a bar and huge breakfast area! Right on sunny beach!

Reviewed on Feb 4, 2026

Hampton Inn & Suites Panama City Beach-Beachfront
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
$99 nightly
The price is $112 total per night from Feb 10 to Feb 11
$112 total
Feb 10 - Feb 11
Total with taxes and fees
9.2/10 Wonderful! (1,620 reviews)
The room was spotless.

Reviewed on Feb 1, 2026

Hyatt Place Panama City Beach
See all 7,767 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 $897 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.