Chipley Vacations from $556

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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
Save 100% on your flight
Price was $967, price is now $556 per person
$556
per person
Apr 3 - Apr 7
found 1 day ago
Roundtrip flight included
Boston (BOS) 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

Camp Creek Inn

Camp Creek Inn

4 out of 5
Save 100% on your flight
Price was $1,447, price is now $1,063 per person
$1,063
per person
Mar 20 - Mar 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Panama City (ECP)
9.8/10 Exceptional! (125 reviews)
My stay at Camp Creek Inn was absolutely wonderful from start to finish. The grounds are stunningly beautiful, the atmosphere is peaceful, and the rooms were comfortable, inviting, and well-appointed. The staff truly made this experience exceptional. Jeff in valet was absolutely amazing, as was the young gentleman who assisted me the night before on 1/2/26 (I unfortunately didn’t catch his name). Both went above and beyond to ensure I was taken care of every step of the way. They were incredibly welcoming, assisted me with my bike, and offered great advice on places to visit and things to do—making my stay even more enjoyable. I would also like to give a special and heartfelt shout-out to Nicole Uribe, who was absolutely wonderful. She made my check-in experience smooth and seamless, took the time to walk me around the main areas of the property, gave me a personal tour, and truly made me feel welcomed. Her warmth and attention to detail were outstanding.

Reviewed on Jan 4, 2026

South Shore 30A by Avantstay Gulf View Pool + Bonfires

South Shore 30A by Avantstay Gulf View Pool + Bonfires

3 out of 5
Rosemary Beach
Save 100% on your flight
Price was $3,399, price is now $2,521 per person
$2,521
per person
Apr 9 - Apr 13
found 4 hours ago
Roundtrip flight included
Minneapolis (MSP) to Panama City (ECP)
6/10 (1 review)
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
Price was $4,672, price is now $3,488 per person
$3,488
per person
Apr 17 - Apr 24
found 1 day 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
$50 nightly
The price is $56 total per night from Feb 16 to Feb 17
$56 total
Feb 16 - Feb 17
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! (2,395 reviews)
Beautiful view, very clean facility and friendly staff!

Reviewed on Feb 9, 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
$101 nightly
The price is $114 total per night from Feb 22 to Feb 23
$114 total
Feb 22 - Feb 23
Total with taxes and fees
9.2/10 Wonderful! (1,644 reviews)
Our room was spotless. The view of the ocean was incredible! We used a chair to prop open the heavy door to sleep with the sound of the water. Breakfast was pretty good and standard, but I would have liked a non-pork meat option. The breakfast attendants were very quick and kept the food stocked ...

Reviewed on Feb 7, 2026

Hyatt Place Panama City Beach
See all 7,745 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 $556 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.