Chipley Vacations from $562

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Panama City Resort & Club by VRI Americas

Panama City Resort & Club by VRI Americas

2.5 out of 5
Price was $680, price is now $562 per person
$562
per person
Jan 4 - Jan 7
found 16 hours ago
Roundtrip non-stop flight included
Baltimore (BWI) to Panama City (ECP)
8.6/10 Excellent! (172 reviews)

Camp Creek Inn

Camp Creek Inn

4 out of 5
Price was $1,644, price is now $1,280 per person
$1,280
per person
Feb 7 - Feb 12
found 1 day ago
Roundtrip non-stop flight included
Baltimore (BWI) to Panama City (ECP)
9.8/10 Exceptional! (159 reviews)
Beautiful property with fabulous amenities.

Reviewed on Oct 19, 2026

The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Price was $2,881, price is now $2,362 per person
$2,362
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Panama City (ECP)
9.6/10 Exceptional! (259 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
Price was $3,760, price is now $3,112 per person
$3,112
per person
Feb 5 - Feb 11
found 14 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Panama City (ECP)
No reviews

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
Price was $2,827, price is now $2,341 per person
$2,341
per person
Dec 18 - Dec 21
found 18 hours ago
Roundtrip non-stop flight included
New York (NYC) to Panama City (ECP)
No reviews

Don't see what you're looking for?
See all available trips from Columbus to Chipley
View all trips

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.
See properties

Chipley Hotel Deals

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
$71 nightly
The price is $80 total per night from Dec 6 to Dec 7
$80 total
Dec 6 - Dec 7
Total with taxes and fees
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
Fully refundableReserve now, pay when you stay
$49 nightly
The price is $55 total per night from Dec 16 to Dec 17
$55 total
Dec 16 - Dec 17
Total with taxes and fees
Chateau Beachfront Hotel, A By The Sea Resort
The Palm & Tide Beachfront Hotel

The Palm & Tide Beachfront Hotel

2 out of 5
12001 Front Beach Rd Panama City Beach FL
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $64 total per night from Nov 16 to Nov 17
$64 total
Nov 16 - Nov 17
Total with taxes and fees
7/10 Good! (373 reviews)
"I’m going to be honest about my stay. I booked and paid for a room that was supposed to sleep 10 people. When I arrived, the hotel gave me a room that only slept four. On top of that, the room smelled horrible. I felt misled by the staff, and I’m frustrated that I paid for accommodations for 10 people ..."

Reviewed on Nov 15, 2026

The Palm & Tide Beachfront Hotel
See all 7,838 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $562 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.