Chipley Vacations from $435

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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 $435 per person
$435
per person
Oct 17 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
10/10 Exceptional! (1 review)
Nice employees clean room would have been perfect if it had a private balcony will come visit again!

Reviewed on Jun 25, 2025

WaterSound Inn

WaterSound Inn

4 out of 5
WaterSound Beach
Save 100% on your flight
Price was $1,937, price is now $1,303 per person
$1,303
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip flight included
Charlotte (CLT) to Panama City (ECP)
9.4/10 Exceptional! (93 reviews)
It’s a beautiful option in a beautiful area

Reviewed on Dec 13, 2024

Embassy Suites by Hilton Panama City Beach Resort

Embassy Suites by Hilton Panama City Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $1,025, price is now $713 per person
$713
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
8.6/10 Excellent! (944 reviews)
Could use a revamp and possibly not have dogs all over the place. Came across several dog poops in their grass due to them allowing dogs to be in that hotel. It was a great location, however. Getting in and out of their self parking was poor due to it, not registering your car when you would come back through the entrance.

Reviewed on Aug 23, 2025

The Pearl Hotel

The Pearl Hotel

4 out of 5
Rosemary Beach
Save 100% on your flight
Price was $2,483, price is now $1,780 per person
$1,780
per person
Nov 14 - Nov 20
found 18 hours ago
Roundtrip flight included
Dallas (DFW) to Panama City (ECP)
9.4/10 Exceptional! (173 reviews)
Nice service, experience and food.

Reviewed on Aug 9, 2025

Bluegreen's Bayside Resort and Spa

Bluegreen's Bayside Resort and Spa

4.5 out of 5
Price was $698, price is now $501 per person
$501
per person
Oct 24 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Panama City (ECP)
7.2/10 Good! (295 reviews)
Absolutely love how clean and well kept the property is. Convenient to choices of things to do like sunset cruises and dolphin watching. Absolutely love the private beach to watch the boats go by. The property is so beautiful. Glad to have access to the very clean pool, laundry room , game room , bikes and spa. I will be booking again real soon.

Reviewed on Aug 13, 2025

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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

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
$51 nightly
The price is $58 total per night from Aug 28 to Aug 29
$58 total
Aug 28 - Aug 29
Total with taxes and fees
7.8/10 Good! (1,781 reviews)
"Would stay again."

Reviewed on Aug 22, 2025

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
Fully refundable
$85 nightly
The price is $96 total per night from Aug 27 to Aug 28
$96 total
Aug 27 - Aug 28
Total with taxes and fees
7/10 Good! (2,331 reviews)
"Love that it was right on the beach. Friendly staff great food within walking distance. Hotel a little outdated but clean no issues. Will stay again. Good value price wise very fair pricing."

Reviewed on Aug 22, 2025

Radisson Beachfront Hotel - Panama City Beach
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
$119 nightly
The price is $134 total per night from Sep 1 to Sep 2
$134 total
Sep 1 - Sep 2
Total with taxes and fees
8.6/10 Excellent! (1,907 reviews)
"We had a good time. No negative things to say."

Reviewed on Aug 23, 2025

Hampton Inn & Suites Panama City Beach-Beachfront
See all 7,815 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.

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Frequently asked questions

How much does a Chipley vacation package cost?
You'll find cheap prices from $435 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.