Chipley Vacations from $482

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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.
Studios at Fontainebleau Terrace

Studios at Fontainebleau Terrace

3.5 out of 5
Price was $688, price is now $482 per person
$482
per person
Mar 13 - Mar 15
found 8 hours ago
Roundtrip non-stop flight included
Detroit (DTW) to Panama City (ECP)
6/10 (2 reviews)
Everything was clean and tidy. I could see the beach from the bedroom window!

Reviewed on Nov 17, 2025

Walk to Seacrest Beach, Resort Pool Modern 3bdr Free Wheelin by Avantstay

Walk to Seacrest Beach, Resort Pool Modern 3bdr Free Wheelin by Avantstay

3 out of 5
Rosemary Beach
Price was $1,569, price is now $1,119 per person
$1,119
per person
Feb 22 - Feb 27
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) to Panama City (ECP)
No reviews
Pura Vida by Avantstay Treetop of Seacrest Beach + Pool, Bonfires

Pura Vida by Avantstay Treetop of Seacrest Beach + Pool, Bonfires

3 out of 5
Treetop
Price was $1,536, price is now $1,104 per person
$1,104
per person
Feb 22 - Feb 27
found 15 hours ago
Roundtrip non-stop flight included
New York (NYC) 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
Price was $4,551, price is now $3,287 per person
$3,287
per person
Mar 8 - Mar 13
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Panama City (ECP)
No reviews
Tipsea Turtle - Avantstay 1 Block to Gulf + Pool

Tipsea Turtle - Avantstay 1 Block to Gulf + Pool

3 out of 5
Bid-a-wee Beach
Save 100% on your flight
Price was $5,625, price is now $4,072 per person
$4,072
per person
Mar 8 - Mar 13
found 2 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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

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
$77 nightly
The price is $87 total per night from Jan 4 to Jan 5
$87 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
8.6/10 Excellent! (2,230 reviews)
Checking was great staff were amazing

Reviewed on Dec 16, 2025

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
$43 nightly
The price is $48 total per night from Dec 20 to Dec 21
$48 total
Dec 20 - Dec 21
Total with taxes and fees
7.8/10 Good! (2,100 reviews)
Amazing

Reviewed on Dec 15, 2025

Palmetto Beachfront Hotel, a By the Sea Resort
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
$52 nightly
The price is $59 total per night from Dec 23 to Dec 24
$59 total
Dec 23 - Dec 24
Total with taxes and fees
7/10 Good! (1,305 reviews)
The whole place is just magical. Its like a place we stayed as kids in the 1980’s. No muss no fuss. Its clean enough, big enough and has a great heated pool

Reviewed on Dec 15, 2025

Chateau Beachfront Hotel, A By The Sea Resort
See all 7,801 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 $482 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.