Chipley Vacations from $1,398

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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.
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 $1,875, price is now $1,398 per person
$1,398
per person
Sep 15 - Sep 19
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
No reviews

Southern Shores by Avantstay Seacrest Beach Resort Pool

Southern Shores by Avantstay Seacrest Beach Resort Pool

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,010, price is now $1,501 per person
$1,501
per person
Sep 15 - Sep 19
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
10/10 Exceptional! (1 review)
Good place to be

Reviewed on Dec 8, 2025

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

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

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,252, price is now $1,691 per person
$1,691
per person
Sep 15 - Sep 19
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
No reviews

Totally Beachin by Avantstay Sleeps 18 Seacrest Beach

Totally Beachin by Avantstay Sleeps 18 Seacrest Beach

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $4,523, price is now $3,403 per person
$3,403
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) to Panama City (ECP)
No reviews

3 Ensuite Bedrooms, Porches & BBQ Near Inlet Beach 30A Ciel Bleu by Avantstay

3 Ensuite Bedrooms, Porches & BBQ Near Inlet Beach 30A Ciel Bleu by Avantstay

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,144, price is now $1,623 per person
$1,623
per person
Sep 15 - Sep 19
found 2 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
No reviews

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Stay near popular Chipley attractions

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.
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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
$129 nightly
The price is $145 total per night from Jul 6 to Jul 7
$145 total
Jul 6 - Jul 7
Total with taxes and fees
7.8/10 Good! (2,629 reviews)
"From check in to check out, everything was excellent. The staff was very friendly. The room was spacious and clean. The view was beautiful."

Reviewed on Jul 1, 2026

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
$178 nightly
The price is $202 total per night from Jul 27 to Jul 28
$202 total
Jul 27 - Jul 28
Total with taxes and fees
7/10 Good! (2,816 reviews)
"Todo bien"

Reviewed on Jun 30, 2026

Radisson Beachfront Hotel - Panama City Beach
Chateau Beachfront Hotel, A By The Sea Resort

Chateau Beachfront Hotel, A By The Sea Resort

2.5 out of 5
12525 Front Beach Rd Panama City Beach FL
$153 nightly
The price is $173 total per night from Jul 5 to Jul 6
$173 total
Jul 5 - Jul 6
Total with taxes and fees
7/10 Good! (1,875 reviews)
"Dont waste your money"

Reviewed on Jul 1, 2026

Chateau Beachfront Hotel, A By The Sea Resort
See all 7,739 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 $1,398 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.